Yet More Molecules with
Silly or Unusual Names

SNOG

SNOG is a utility carrier of nitric oxide which breaks down to produce nitric oxide and a glutathione radical at pH 7.4. Its proper chemical name is S–Nitrosoglutathione. Unsurprisingly, one effect of SNOG is that it apparently causes smooth muscle relaxation... For those of you unfamiliar with UK slang, a 'snog' is a deep passionate kiss, similar to the one Britney is giving Madonna in the photo on the right...

Thanks to Mackay Steffensen from Oxford University for suggesting this molecule.


Hirsutene

This is an important biological molecule, although what its function is, I'm not sure. Perhaps it makes things hairy...?

Forskolin

Despite the odd name, forskolin is not what they remove from the baby during ritual circumcision. In India, practitioners of traditional Ayurvedic medicine have long used the herb Coleus forskohlii to treat asthma, heart disease, and a range of other ailments. In the 1970s, researchers isolated a chemically active ingredient in the herb and called it forskolin. Now available in supplement form, this extract is commonly recommended for treating hypothyroidism, a condition in which the thyroid gland produces too little thyroid hormone. Forskolin is believed to stimulate the release of thyroid hormone, thus relieving symptoms as fatigue, depression, weight gain, and... dry skin.

Thanks to Kyle Daly for suggesting this molecule.

Wrenchnolol

This is a molecule that looks like a wrench, and is an anti-cancer drug. The "jaw" part of the compound mimics the helical interface of the activation domain of a transcription factor molecule, and the "handle" region accepts chemical modifications for a range of analysis.

Thanks to Mackay Steffensen for suggesting this molecule. More details: J. Am. Chem. Soc. 126 (2004) 3461.

Sex Muscle Abnormal Protein 5

The European Bioinformatics Institute houses the Macromolecular Structural Database, and for quite a few years the most downloaded structure from that site was PDB code 2SEM: it contained a protein called "Sex muscle abnormal protein 5". Obviously, search engines had indexed all the PDB files, and you can guess what kind of searches had returned this structure! The protein comes from Caenorhabditis Elegans, which is a tiny worm (about 1 mm long) and was the first true animal to have its genome completely sequenced. The people who reported this protein were investigating its crucial role in the development of the worm's vulva (Clark et al, Nature, 1992 Mar 26, 356(6367):285-6). As the amount of dubious material available on the internet has grown, interest in this protein from persons 'outside the scientific community' has declined. On a similar theme, there's another molecule called SexA I, which is a restriction enzyme from Streptomyces exfoliatus that cleaves the DNA sequence A/CCWGGT.

Thanks to Peter Keller of the Macromolecular Structural Database, European Bioinformatics Institute, and Lily Zhou from the University of Michigan, for suggesting these molecules and telling me their details.

Sillimanite

This mineral wasn't named after the clumsy fool that tripped over it, but was named in honour of the American mineralogist Benjamin Silliman (1779-1864), who was a chemistry professor at Yale. It is a form of aluminium silicate, with no real value, except in Idaho, where the Clearwater River Valley has sillimanite cobbles that are carved into figurines and sold as souvenirs of Idaho.

Thanks to Hope Nesmith for suggesting this mineral.

Indenyl

This sounds like it could be a pollutant found in some Egyptian rivers (i.e. in de Nile...), but it's actually a fusion of a cyclopentadienyl ring with a benzene ring, and is often used as a ligand for metallocene synthesis.

Thanks to Kenneth Koon for suggesting this radical.

Thebacon

This molecule certainly brings home the-bacon. It has a similar structure to diamorphine (heroin) but has only one acetyl group instead of two, and the other group is replaced with a CH3O- group. Apparently, thebacon hydrochloride is a centrally acting cough suppressant sometimes used to treat coughs. This molecule isn't to be confused with BaCoN (barium cobalt nitride), which is a black crystalline solid with a layered structure (strips of BaCoN?)

Thanks to Matt Wright from University Hospital Birmingham NHS Foundation Trust and Aston University, and Bastiaan Vos for suggesting these molecules. More info in BaCoN from: A. Tennstedt and R. Kniep, Z. anorg. allg. Chem. 620 (1994) 1781.

Cryogenine

Cryogenine A (also known as Vertine) is the active constituent of Sinicuichi plant. It apparently can give audio hallucinations, but I don't know why it is called cryogenine...maybe because after you stop using it you go through very, very cold turkey? In fact there are two totally unrelated, and different molecules called cryogenine. The other one, Cryogenine B, is usually called phenylsemicarbazide, and has been found to be carcinogenic in mice.

Thanks to Michael F Aldersley from Rensselaer Polytechnic Institute, Troy, NY, for suggesting this molecule, and to Fox for info on Cryogenine B.

Lagerine and Bebeerine

I wonder if lagerine is sold by the pint? It actually has nothing to do with beer, it gets its name from being a constituent of the crape myrtle (Lagerstroemia indica L.) plant. Bebeerine too, has nothing to do with beer. It's an alkaloid molecule derived from the Caribbean bebeeru tree, and helps to protect it from beetles.

Thanks to Michael F Aldersley from Rensselaer Polytechnic Institute, Troy, NY, for suggesting this molecule. Ref: E. Spath, F. Kuffner, Ber. Deutch Chem. Gess. 67 (1934) 55.

Jawsamycin, Histrionicotoxin and Yessotoxin

These three molecules are all highly toxic, and are normally isolated from biological sources. Jawsamycin was discovered in 1989 by Fujisawa, a Japanese pharaceutical company, it has only recently been synthesised. The metabalite is composed of a chain of five carbon triangles (cyclopropyls), giving it its name because of the resemblance to shark's teeth. The compound, however, has 10 chiral centres, points about which mirror images of the molecule can form for a total of 1024 possible isomers, only one of which is jawsamycin.
Histrionicotoxin is a poison found on the skin of a certain tree frog in South America (Dendrobates histrionicus), and is used by the native indians on their blow-pipe darts.
Yessotoxin was first isolated from the digestive organs from scallops (Patinopecten yessoensis) in Japan and is believed to be produced by microalgae.

Thanks to James Waterman from Nottingham University for suggesting these molecules.

Sarcosine

This is one for all our French readers... Nicolas Sarkozy (right) is currently the President of France, and, as such, it's appropriate that he has a molecule with a similar name. Sarcosine is a sweetish crystalline amino acid found in muscles and other tissues, and is also called N-methylglycine. A functionalised version of this, N-laurylsarcosine, is known as 'sarkosyl detergent', which is an anionic surfactant perhaps reflecting the detergent effect of the French president.
Another molecule which sounds odd in French (but not in English) is pyralene, which has been used in the past as an insulating oil in electric transformers. In French it is pronounced "pire haleine", which means "worst breath". This is ironic, since use of pyralene was abandoned after transformer fires were giving off toxic fumes.

Thanks to Thomas Jeanmaire for suggesting sarcosine, Christophe Brun for info about sarkosyl detergent, and Marc Schaefer for the translation of pyralene.

Enflurane

Yet another one for the French speakers... Enflure in French means a twit, a clot, or a jerk, or can also mean a swelling or inflamation. Enflurane is an outdated halogenated ether that was commonly used for inhalation anesthesia during the 1970's and 1980's. A curious (but apparently true) story about enflurane relates to its pre-human work. Enflurane and Isoflurane are isomers, and they were being investigated for their safety and efficacy as anaesthetics. Isoflurane is by far the better of the two, but was initially held back from clinical use because test experiments showed it gave cancer to rats. It turns out that the rats that were given enflurane were given different food to the ones using isofluran, and those exposed to isoflurane were being fed pellets which had become contaminated with a known carcinogen. By the time the toxicity experiments were repeated (and isoflurane found to be innocent in this regard), the poor relation, enflurane (which had passed all the previous tests with flying colours), had already been on the market for a few years. Had the contamination not occurred, it is doubtful that enflurane would ever have made it on to the market at all. Enflurane was never popular, and its manufacture has ceased because the makers could not sell enough of it to make its production economical. Isoflurane, meanwhile, led the way as the mainstay of inhalational anaesthesia in the Western world for several decades.

Thanks to Thomas Jeanmaire for suggesting this molecule, and to Ken Ruiz for the isoflurane story.

Shikimic Acid

Here's one for our German-speaking readers. Shikimic sounds very like the German word 'Schickimicki', which means a (snobbish) member of the in-crowd, a trend-setter, or a 'designer-label-wearing' sort of person, for example, Posh and Becks in the picture, left. Shikimic acid was first isolated from the Japanese flower shikimi, hence its name. It's used as a starting molecule in the synthesis of the anti-flu drug Tamiflu.

Thanks to Kutti for suggesting this molecule.

Mandelic Acid

Mandelic acid is not named after Nelson Mandela, the world famous South African polician and winner of the 1993 Nobel Peace Prize, although his youthful appearance might be due to it....as mandelic acid is often used in skin creams to smooth away wrinkles. It's also used as an antiseptic ingredient particularly against urinary tract infections. An interesting related anecdote is that a chemist called Leon Mandel from Emory University in the US, gave a talk at Princeton in the mid-60s on the total synthesis of leontine, an alkaloid. He said his final step was to be the reaction of leontine with mandelic acid (yielding, of course, leon(tine) mandel(ate)).
Mandelates do actually exist, as in the title of this paper from the University of Cape Town (of course): "Quininium mandelates - a systematic study of chiral discrimination in crystals of diastereomeric salts". Is this, perhaps, the first association between Mandela and discrimination?

Thanks to Antony Bigot for suggesting this molecule, to Bob Buntrock for the leontine mandelate anecdote, and to Simon Cotton for the paper on mandelates.

Soddyite

This is a silicate mineral that was named after Frederick Soddy (1877-1956), the British physicist and radiochemist. In German it's known as Soddyit and it has the formula (UO2)2SiO4·2H2O.

Thanks to Sean Pearce for suggesting this mineral.

Kutnahorite

This is a another mineral that geology students love to mispronounce as "cuttin' a whore right". It's a CaMn(CO3)2 mineral originally from Czechoslovakia, and described as a massive and granular material occurring in veins. Its color is almost always some shade of pink, with well-developed cleavage with cleavage surfaces that are commonly curved (aren't they always?).

Thanks to Dave Chapman and Jason Stouffer for suggesting this mineral.

Mucic Acid

Pronounced 'Music acid', this is quite different to Acid Music... This chemical is obtained by the nitric acid oxidation of milk sugar (lactose), dulcite, galactose, quercite and most varieties of gum. It is also called Galactaric Acid. The "mucic acid test" in basic biochemistry lab is a well-known test for D- or L-galactose. The test is carried out by oxidising the sample with concentrated nitric acid; mucic acid crystals will form after leaving the solution overnight. Isn't chemistry great? Just add some acid, and you get some music...

Thanks to Warut Roonguthai for suggesting this molecule.

Burpalite

This mineral with the wonderful name of burpalite, Na2CaZrSi2O7F2, is named after the Burpala massif in Buryatia, Russia. It sounds a bit like a medicine you give to babies to make them burp...

Thanks to Willem Schipper for suggesting this mineral.

Rhamnetin

This molecule with an amusingly double-entendre name (ram'n it in) actually gets its name from the Buckthorn berry (Rhamnus cathartica), of which it is a derivative. It is a yellow pigment used in the dye industry.

Thanks to Geoff Hallas for suggesting this molecule.

DNA origami

This is a new development in which strands of various lengths of DNA can be 'stitched' together to make nanoshapes. The picture (left) shows AFM images of just some of these shapes (scalebar = 100 nm), including nanostars, and nanosmileys, but you can even write nanomessages using nanoletters and draw nanomaps of the world (see below).

One obvious application of patterned DNA origami would be the creation of a ‘nanobreadboard’, to which diverse components could be added. The attachment of proteins, for example, might allow novel biological experiments aimed at modelling complex protein assemblies and examining the effects of spatial organization, whereas molecular electronic or plasmonic circuits might be created by attaching nanowires, carbon nanotubes or gold nanoparticles.

See: P.W. Rothemund, Nature 440 (2006) 297.

Olympiadane and Olympicene

Olympiadane (left) consists of five tiny interlocking rings, which mimics the Olympic Games symbol, and so is named 'Olympiadane'. It was first made in 1996, in commemoration of that year's Olympic Games. The successful linkage of these highly complex synthetic molecules means that molecular chains of any length could be constructed with many applications, particularly in the areas of information storage systems and the creation of a 'molecular computer'. Similarly, olympicene is a fragment of a graphene sheet comprising 5 rings. The image on the left is of the actual miolecule taken by atomic force microscopy. It was made by chemists at the University of Warwick in the Uk, after a request by the Royal Society of Chemistry to make the molecule to commemorate the 2012 London Olympics.

Thanks to Wendy Hunt for suggesting Olympiadane, and to Charles Turner and Victoria Ludowici for Olympicene. Ref: BBC news 2012

AFM image of olympicene

MAP-kinase-kinase-kinase

Mitogen-activated protein (MAP) kinases are proteins that respond to extracellular stimuli (mitogens, e.g. a chemical or protein) and regulate various cellular activities, such as gene expression, mitosis, differentiation, and cell survival or death. In the cell signalling pathway for inflammation there is a MAP-kinase, and of the couple of dozen things activated by this, one is (MAP-kinase)-activated protein kinase, sometimes shortened to MAPKAPK-2. Another is ((MAP-kinase)-activated protein kinase)-activated protein kinase, or MAPKAPK-3. Sometimes this is just shortened to 'MAP-kinase-kinase-kinase'. It's a good thing that the next things downstream had already been given their own names. If they, too, had been named functionally, we would have MAPKAPKAPK, MAPKAPKAPKAPK, and so on, in a stuttering series of speech impedimentia.

Thanks to Leigh S. Arino de la Rubia for suggesting this molecule, and to Rick Bryan for more information on the nomenclature.

Coproverdine

This molecule is a new anti-tumor drug that was isolated by the University of Canterbury (Christchurch, New Zealand) from a sponge which was discovered off the coast of New Zealand. In the National Institute for Water and Atmospheric research (NIWA) archives, it is recorded as being "Green-sheep-sh*t like in appearance". The alkaloid they discovered was cytotoxic, but they needed a catchy name for it. They settled on "Coproverdine": Copro - sh*t, Ovis - sheep, and verdi - green.

Thanks to Martin Lee from the University of Canterbury, NZ, for suggesting this molecule, and who apparently spent a year trying to make it! Ref: S. Urban, J.W. Blunt, M.H.G. Munro, J. Nat. Prod. 65, (2002) 1371.

Labradorite

Labradorite is a silicate mineral that is named after Labrador in eastern Canada, where it was first discovered. Labradorite can produce a colourful play of light across cleavage planes and in sliced sections, called labradorescence, which sounds a bit like a perfume based on the smell of old dogs, or maybe the glow from a radioactive dog! The usually intense colours range from the typical blues and violets through greens, yellows and oranges. The colour display is from lamellar intergrowths inside the crystal.

Thanks to Chris Miller for suggesting this mineral.

'Banana' Borane

This isn't an official name, but I'm told that many chemists who work in the organoborane field use the nickname 'banana borane' to describe molecules such as 9-borabicyclo[3,3,1]nonane, abbreviated BBN. This is because rather than draw out the proper structure (top), they simply draw the borane as a banana shape with the bridging B group sticking out.

Thanks to Rob Saunders for suggesting this fruity molecule and for a link to it in a thesis.


Skunky Thiol

This molecule is what makes beer taste bad after it's been left exposed to sunlight for a few hours. The actual name is 3-methylbut-2-ene-1-thiol, or 3-MBT for short, but since it's related to molecules found in skunk spray, and it stinks, it's also known as skunky thiol. Only a few nanograms of this thiol in one litre of beer are enough to give the offensive flavour.

Thanks to Matthew Latto for suggesting this smelly molecule. More info: K. Huvaere et al., Photochem. Photobiol. Sci., 5 (2006) 961.

Fartox

On a related theme, this molecule is actually called pentachloronitrobenzene, but goes by a variety of tradenames, including Quintozene, Earthcide and best of all, Fartox. It seems somehow appropriate that Fartox should be a pale yellow solid with a slightly musty odour. It has been used as a soil fungicide since the 1930's, but I have no idea how it came to have this silly name. Maybe it was due to a side-effect of eating fruit sprayed with it?

Dinocap

Dinocap sounds like a dinosaur's hat, or a hat that looks like a dinosaur. It's a dark red viscous liquid that's used to kill mites, fungus and mildew on crops, and goes by the trade name Karathane. There are 2 different versions of dinocap; dinocap-4 is the one shown on the left, and dinocap-6 has the positions of the two blue side-groups swapped. In either case, the liquid is actually a mixture of different isomers, with R1=CH3(CH2)n and R2=CH3(CH2)5-n. I'm pretty sure the 'dino-' part of the name comes from 'dinitro-', and the 'cap' part may be because of it being an ester between crotonic acid and the phenolic rest of the molecule.

Thanks to Brendon Bosman for suggestions about the origin of the name.

Naftazone

This sounds like a pretty naff molecule. (For non-UK readers, 'naff' is English slang for poor quality, unfashionable or rubbish). It's used as a drug to protect blood vessels (a 'vasoprotector') - so, maybe it's not quite so naff after all. Its name comes from a contraction of its full name (1,2-naphthoquinone-2-semicarbazone) and has nothing whatsoever to do with the North American Free Trade Agreement (NAFTA).

NUN

This molecule could be habit-forming...It's actually a linear molecule of uranium nitride N-U-N, made by inserting uranium atoms into molecular N2.

Thanks to Ian for suggesting this pious molecule. More info: R.D. Hunt, J.T. Yustein and L. Andrews, J. Chem. Phys., 98, (1993) 6070.

Discodermolide

Could this be John Travolta's favourite molecule? It's a recently discovered polyketide natural product found to be a potent inhibitor of tumor cell growth, and it gets its name since it was first isolated in 1990 from the Caribbean marine sponge Discodermia dissoluta. Since the compound is light-sensitive, the sponge must be harvested at a minimum depth of 33 metres - so, no disco lighting there then...
An unrelated group of alkaloids isolated from from New Zealand marine sponges are called discorhabdins.  I'm told that groups that work with these compaounds refer to them as 'disco(s)' for short.

More info: Wikipedia. Thanks to Dr Dave Fairley from Singapore for the info about discorhabdins.

Jimthompsonite

This is actually a mineral - a mixture of iron and magnesium silicates, with formula (Mg;Fe2+)5Si6O16(OH)2 - that's found in a talc quarry, near Chester, Vermont, USA. It was named after Professor James Burleigh Thompson, Jr., who was an eminent petrologist of Harvard University in the 1940s and 1950s. This is a different Jim Thompson to the one who helped establish the silk industry in Thailand. There's a slightly different version (monoclinic crystal) of this mineral called clinojimthompsonite.

Thanks to David French for suggesting this mineral.

Pregnane

This is a steroid molecule that is the parent compound for many hormones, including the pregnancy hormone progesterone.

Thanks to Vincent Schüler for suggesting this molecule.

Asparagine

I wonder if this molecule tastes of asparagus? In fact it gets its name since it was first isolated in 1806 from asparagus juice, and was the first amino acid to be isolated. It is one of the 20 most common natural amino acids on Earth and can be synthesised in the body. Interestingly, the smell observed in the urine of some individuals after consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol.

Thanks to Vincent Schüler for suggesting this molecule.

Analcite

I thought it was time to show you my analcite! Actually it's a mineral, and although analcite is a valid name for it, it normally goes by the less amusing name of analcime. It's a form of sodium aluminium silicate, and it gets its name from the Greek word meaning 'weak', referring to a weak electrical charge developed on rubbing. So if you rub your analcite, you may get a shock...

Thanks to Daniel Manke of Central Michigan University for suggesting this mineral.

Gingerol

Gingerol isn't the molecule responsible for ginger hair and freckles. Instead, it's the active constituent of fresh ginger. Gingerol is a relative of capsaicin, the compound that gives chilli peppers their spiciness. It's normally found as a pungent yellow oil, but also can form a low-melting crystalline solid. Cooking ginger transforms gingerol into the compound with a 'zing', zingerone.

Thanks to Neil Anderson from Denmark for suggesting this molecule.

Porphyrin Hamburger

A team of researchers at Osaka University, Japan, fused a molybdenum-porphyrin complex and a tungsten polyoxometalate to form a compound they have named the 'porphyrin hamburger'. Two saddle-shaped porphyrin complexes make up the burger buns, while a cluster of tungsten oxide anions surrounding a central silicon cation, known as a polyoxometalate, forms the meat sandwiched between them. The molecules are joined by stable coordination bonds.

This must give plenty of opportunity for derivatives along the lines of Porphyrin Cheeseburger. Or perhaps you could even attach penguinone to make a penguin burger? Or even attach a molecule of cocaine to get a burger and coke?

Thanks to Matt Latto for suggesting this molecule. Original article: A. Yokoyama, T. Kojima, K. Ohkubo, S. Fukuzumi, Chem. Commun., (2007), DOI: 10.1039/b704994c


The porphyrin hamburger: W atoms are shown in pink, O in red, Mo in green, C in grey and N in blue. The central Si ion is shown in dark grey.

Folk Acid

This is nothing to do with folk music, or even acid folk, it is simply a mis-spelling of folic acid, which itself gets its name from the Latin word folium meaning 'leaf'. This seems to be a particlarly common mis-spelling, and occurs even in scientific papers and textbooks (try it on google), maybe a result of word-processing programs automatically 'correcting' words they don't recognise, or just that scientists can't spell.

Thanks to David Bromage from the Australian National University for suggesting this molecule.

PORN

Now that we have the word 'PORN' on this site, it'll either get banned or increase the hit rates hugely! Unfortunately, this PORN is simply the acronym for poly-L-ornithine, a molecule used in cell culture experiments. I suppose that to form a polymer it does involve lots of frantic couplings...so PORN maybe isn't such an inappropriate name after all.

Thanks to Debbie Radtke for suggesting this molecule.

CuNT

This one must be mother of all silly acronyms! Carbon nanotubes are often abbreviated to CNTs, and single-walled ones to SWCNTs. But when a Chinese group recently fabricated copper nanotubes, unbelievably they decided to call them CuNTs! In the same paper they describe bismuth nanotubes, and called them BiNTs. Either they named these 2 structures for a bet - just to see if the Royal Society of Chemistry would publish a paper containing numerous (over 50!) references to BiNTs and CuNTs, or they just didn't realise the meanings of these two acronyms. Or maybe they just did it to increase the number of hits they receive from online searches...

Thanks to Keith Bromley for spotting this paper, which is: D. Yang, G. Meng, S. Zhang, Y. Hao, X. An, Q. Wei, M. Yea and L. Zhang, Chem. Commun., (2007), 1733.

Scorpionate ligands

The scorpionate ligand gets its name from the fact that the ligand can bind a metal with two donor sites like the pincers of a scorpion. The third donor site reaches over the plane formed by the metal and the other two donor atoms to bind to the metal, like a scorpion grabbing the metal with two pincers before stinging it. The most popular class of scorpionates are the tris(pyrazolyl)hydroborates or Tp ligands, and this is shown bonding to a Mn(CO)3 group, below. Another scorpion-like molecule is bis([1,2]dithiolo)-[1,4]thiazine, which is sometimes unofficially called scorpionine.

Thanks to Warut Roonguthai for suggesting these two molecules. For more details see: http://en.wikipedia.org/wiki/Scorpionate_ligand, or http://www.chm.bris.ac.uk/motm/sscorpionine/sscorpionine.htm

Puberulin

This wonderfully named molecule gets its name from the fact that it's isolated from the African shrub A. puberula. Hmm, I wonder what you'd measure with a pube-rula...

For more details see: S.A. brown, R.E. March, D.E.A. Rivett, H.J. Thompson, Phytochem. 27 (1988) 391.

Bender's salt

Is this what gay chemists put on their fries? (In the UK, a 'Bender' is a derogatory slang name for a male homosexual). Or maybe it's the salt that Bender from Futurama would use. It's potassium ethylthiocarbonate (C3H5KO2S) and is named after the German Chemist Friedrich Bender.

For more details see: R. Fischer, G. Fessler, Pharmazie. 10 (1955) 349.

Biline

A reporter's favourite molecule? (They always want their by-line). This is a bile pigment, and there are various versions depending upon which nitrogen the H goes (in the diagram it's on N-21, so the molecule shown is 21H-biline), and what side chains (if any) there are.

Blasticidin

And here's one for the military, or maybe just a gung ho chemist (Blast its side in!). It's actually an antibiotic fungicide, and is also used in genetic engineering experiments to fuse pieces of DNA together to make resistant genes.

For more details see: http://www.blasticidin.com.

Noselite

A superb mineral name, that sounds like just the sort of thing a geologist needs to find his way around ina dark cave. It's a silicate mineral with formula Na8[SO4|Al6Si6O24], and named after the German mineralogist Karl Wilhelm Nose, and also goes by the name of nosean - as in "I've just been nosean around this rock face". For experiments involving real nose-lights, where the researcher stuck lightbulbs up the noses of volunteers to see how it affected their visual performance, see the wonderfully bonkers paper by N.E. Wetherick (Nature 266 (1977) 442.)

For more details see: http://www.webmineral.com. Thanks to Peter Rice for the Nature reference.

Brick Acid

'Brick acid' is the nickname given to good old hydrochloric acid (a.k.a. muriatic acid), since it's commonly used by builders to clean up the mortar smudges in brickworks and paving. Some manufacturers sell 'brick acid' as a mixture of 10-30% aqueous HCl with added detergent and sulfuric acid.

Thanks to Michael Buxton for suggesting this molecule.



Pigeonite

Pigeonite is a silicate mineral named after Pigeon Point in Minnesota where it was first found. It forms dark green crystals that are found in volcanic rocks on Earth and in meteorites from Mars or the Moon. Those darn pigeons get everywhere...

Thanks to Dennis J. Walden for suggesting this mineral.



MEAN

MEAN is definitely a mean molecule. It stands for monoethanolamine nitrate, which is an explosive used as a sensitiser in 'slurry explosives' (mixtures of ammonium nitrate, sodium nitrate, a gelling agent and water). Slurry explosives are sometimes used in mining and quarrying, but nowadays they are on various governments' watch-lists as potential terrorist weapons due to their ease of manufacture. I believe it's also used in small quantities as a fertiliser, and doesn't cost too much - so it's a favourite with mean gardeners.

Thanks to Maxime Van den Bossche for suggesting this mean molecule.



Duranterectoside

I'm not sure I like the sound of an 'erectoside'...it sounds like it's a sort of reverse-Viagra! Actually it's a type of glucoside derived from the Japanese plant Duranta erecta. There are several different versions, the one shown is duranterectoside A.

Thanks to Bastiaan Vos for suggesting this molecule. For more details see: Y. Takeda, et al, Phytochem. 39 (1995) 829.



Star Wars 'Tie-Fighter' Molecule

It looks like chemists are trying to outdo each other with making molecules which have weird shapes. This one is described in the paper as being shaped like the Tie-Fighters from the movie Star Wars, and may be used to harvest light in photoelectronic applications. Is this in order to stop everyone going to the dark side...? They are made from a central buckyball with two cyanine 'plates' on each side. Perhaps if many of these were joined together, they could make a light sabre...?

Thanks to Jan Linders for suggesting this molecule. For more details see: F. D'Souza, S. Gadde, M.E. El-Khouly, M.E. Zandler, Y. Araki and O. Ito, J. Porphyrins & Phthalocyanines, 9, (2005) 698, "A supramolecular Star Wars Tie Fighter Ship: electron transfer in a self-assembled triad composed of two zinc naphthalocyanines and a fullerene."



Chitose

This molecule also has the same name as the Japanese city, and is also a common Japanese girl's name. The molecule is a sugar, and gets its name since it's derived from chitin, which comes from the Greek for 'tunic' (chiton). Chitose is one of those molecule names that you have be careful to pronounce, as some people pronounce the 'ch' as 'sh', which makes it sound like an unfortunate toilet accident.

Thanks to FengJun for suggesting this molecule.



Whisky Lactone

Whisky lactone, also known as β-methyl-γ-octalactone or quercus lactone (from the Latin for oak tree Quercus alba), is a flavouring found in American bourbon whiskies, and is also found in all types of oak. The flavour gets into the whisky when it's matured in oak barrels. The pure molecule has a fierce, strong, and sweet smell and can be dissolved in alcohol in any proportion.

Thanks to Charles Turner for suggesting this molecule. See: L. Poisson, P. Schieberle, J. Agric. Food Chem. 56 (2008) 5820.



Ranasmurfin

Ranasmurfin has nothing to do with the blue cartoon Smurfs from Belgium. But it is blue! It's an unusual blue protein isolated from the nests of a Malaysian tree frog, Polypedates leucomystax. During mating, the female produces a protein-rich fluid that she and the male frog, whip up into a sticky foam nest containing the fertilized eggs. These nests exhibit a variety of colours - when first formed they are usually pale creamy white/orange, but frequently develop a darkblue/green color within a few hours or days. This blue colour is due to the protein ranasmurfin.

Thanks to Jan Linders for suggesting this protein. See: M. Oke, et al, Angew. Chem. Int. Ed. 47, (2008) 7853.



Bottle-brush polymers

Bottlebrush compounds are usually polymers in which the main chain adopts an extremely stiff conformation, which is surrounded by expanded but still flexible side chains, thus making the molecules resemble the bottle-brushes used for cleaning test-tubes and, er, bottles, in any chemistry lab.

Thanks to Jan Linders for suggesting this polymer. See: M. Wintermantel, et al, Macromolecules 29, (1996) 978.


Top: A bottlebrush polymer. Bottom: A real bottle brush



Morpholino

A Morpholino sounds like an expensive type of coffee available at Starbuck's ("I'll have a cappucino and my wife will have a morpholino, no sugar"). In fact, Morpholinos are synthetic molecules which result from a redesign of natural nucleic acid structures. They are usually 25 bases in length and they bind to complementary sequences of RNA and modify gene expression. The word "morpholino" can occur in other chemical names, referring to chemicals containing the 'morpholine' ring (shown in the picture). To help avoid confusion between the 2 types of molecules with the same name, when describing the nucleic acid version "Morpholino" is often capitalized. Because of the amine group, morpholine is a base, and it's commonly added in ppm concentrations in power plant steam systems to adjust the pH. Its conjugate acid is given the wonderful name 'morpholinium', e.g. in the salt morpholinium chloride.

See: J. Summerton and D. Weller, Antisense & Nucleic Acid Drug Development (1997) 7 187



Studtite and Metastudtite

Studtite isn't the glue which keeps tongue-studs into place, nor is it the secret formula for Hollywood male actors. It's actually a uranium mineral containing peroxide of formula (UO2)O2·4(H2O) formed by the radioactive decay of nuclear fuel or uranium ores. It occurs as white yellow needle-like crystals, and as a mineral it was named for Franz Edward Studt, a English prospector and geologist who was working in the Belgian Congo.

Thanks to Charles Turner for suggesting this mineral. For more info, see webmineral.com.



N-Confused Porphyrins

If you thought chemistry was confusing, here's your proof - even the molecules are confused! "N-confused" porphyrins are so named because instead of have 4 N's in the central core, they have 2 or 3, making them asymmetrical. These rings, often called 'mutated porphyrins', are not planar, but are twisted. The core H's can flip from one N to another, making the molecule twist and change shape. No wonder they're confused...

Thanks to Joannes T.M. Linders for suggesting this confused molecule. For more info, see J.L. Sessler, Angew. Chem., Int. Ed. Engl. 33 (1994) 1348.



Clintonioside

Staying on the presidential theme, clintonioside is not a molecule specially designed to rid the world of the Clintons. It's a steroidal glycoside extracted from the East Asian plant Clintonia udensis. According to the paper below, the rhizomes of this plant have long been used in traditional Chinese medicine for the treatment of fatigue and 'blow' - which is most appropriate given Bill Clinton's past history...

Thanks to Joannes T.M. Linders for suggesting this molecule. For more info, see Y. Mimaki, K. Watanabe, Helvetica Chimica Acta 91 (2008) 2097.



HAMLET

If you take normal α-lactalbumin (see structure, right), and chemically treat it so it folds up in a specific way, you can change it to be (or not to be?) lethal to cancer cells. Thus, we get HAMLET, human alpha-lactalbumin made lethal to tumor cells. So, as the great man said: "Diseases desperate grown, By desperate appliance are relieved, Or not at all." - William Shakespeare, Hamlet, 4.3.

Thanks to Joannes T.M. Linders for suggesting this literary molecule. For more info, see M. Svensson, A. Håkansson, A.-K. Mossberg, S. Linse, and C. Svanborg, P.N.A.S. 97 (2000) 4221, or the superbly titled paper "Who Is Mr. HAMLET?", E.L. Knyazeva, V.M. Grishchenko, R.S. Fadeev, V.S. Akatov, S.E. Permyakov, and E.A. Permyakov, Biochem, 47 (2008) 13127.


α-lactalbumin
"The devil hath power To assume a pleasing shape." - William Shakespeare, Hamlet, 2.2.



Abyssomicin

Abyssomicins are a class of antibiotics that were found in marine creatures that were collected from a depth of 289 m below the surface of the Sea of Japan. This habitat, 'the Abyss', decisively influenced the naming of this class of natural product, which became known as abyssomicins. Different versions were given different code letters, B, C (shown left), D, etc, but curiously, the letter A was left out of the naming, as if that privilege was reserved for an important compound yet to be discovered from the same source.

Thanks to Joannes T.M. Linders for suggesting this molecule. For more info, see "Discoveries from the Abyss: The Abyssomicins and Their Total Synthesis", K.C. Nicolaou, S.T. Harrison, J.S. Chena, Synthesis, (2008).



Poster from the movie "The Abyss".



Elephantin

There are a whole bunch of naturally occurring sesquiterpenes that have been isolated from the plant Elephantopus elatus Bertol (a.k.a. 'Tall Elephantsfoot' or 'Florida Elephant's-Foot'), and which have been given the prefix 'elephant-' as a result. There's elephantin (structure shown in the picture), elephantol, elephantopin, and dihydroelephantolide. Most of the compounds are cytotoxic and have antileukemic activity. I bet chemists have great fun ordering a flask to do reactions with this compound: "Can I have a round-bottomed flask?" "How big?" "Big enough to fit an elephatin!"

Thanks to J.J. Keating for suggesting these molecules. For more info, see: S.M. Kupchan et al, J. Org. Chem. 34 (1969) 3867.



Persinol

Here's another molecule - and this time it's persinol ! Persinol (structure, right) is a a flavanone derived from the Asian-African herb Aerva persica and is believed to have anti-oxidant properties. A similarly named, but completely different, molecule is persin, which comes from a variety of Guatemalan avocados (Persea americana). This toxic chemical causes damage to the mammary tissues of animals that eat the leaves of this avocado plant, stopping milk production.

Thanks to Kay Dekker for suggesting these molecules. For more info, see: E. Ahmed et al, Arch. Pharm. Res. 29 (2006) 343, and Toxic plants and other natural toxicants by T. Garland and A. C. Barr (CABI, 1998), Chapter 19.



Fawcettimine

Unfortunately, this molecule was not named after Charlie's Angel's star Farrah Fawcett Majors. Instead it was named this way because it was isolated from the Jamaican moss Lycopodium fawcetti.

Thanks to Jan Linders for suggesting these molecules. For more info, see: X. Ma and D.R. Gang, The Lycopodium alkaloids, Nat. Prod. Rep. (RSC, 2004), or J. Org. Chem. 1989, 54, 1548.



Pimpinellin

Pimpinellin sounds like the smooooothest of all molecules... or, alternatively, one that forces other molecules to interact with other molecules. In fact it is a furocoumarin extracted from the roots of the cow parsnip plant. It is thought to be phototoxic, so that if someone ingests this molecule, they become sensitive to light. The molecule probably gets its name from the plant genus Pimpinella, from which I assume it was first isolated (can anyone let me know if that's correct?).

Thanks to Christian Pierce for suggesting this molecule.



Micrococcin

The antibiotic micrococcin is a potent growth inhibitor of the human malaria parasite. It gets its name since it's obtained from a bacterium of the genus Micrococcus isolated from sewage. Apparently, male chemists synthesising this molecule are often very reticent to talk about their work for some reason... Maybe it's because they keep getting asked if they've managed to get their micrococcin yet.

Thanks to Frank Moffatt for suggesting this molecule.



Siamese Twin Molecules

In nature, peptide molecules often cyclise into rings. Sometimes these rings are doubled, with a portion of each ring being shared by each partner. Owing to the resulting proximity of both structurally identical cycles, they have been called 'Siamese depsipeptides', since they resemble conjoined twins or 'Siamese' twins. Two examples made from the starting peptide sansalvamide (SA) are shown in the diagram on the right, where the bold bonds indicate the shared atoms.

Thanks to Jan Linders for suggesting these molecules. Ref: Angew. Chem. Int. Ed. 2009, 48, 8564.



NanoPaNTS, Nanokebabs and Nanodumbbells

Nanopants sound like the clothing required for the Nanoputians we saw earlier. And are nanokebabs what they eat when coming home from the nanopub late at night, just in time for them to do a workout with their nanodumbbells? In fact both these 'molecules' are combinations of nanotubes and nanoparticles. NanoPaNTs are nanotubes that have had metallic nanoparticles attached to their ends using magnetic fields. They can give rise to dumbbell-like structures as shown left. Again using magnetic fields, nanotubes can be made to curl back on themselves to make rings, and straight nanotubes can be threaded through these to make shish-kebab-like structures, as shown right. If you think I'm making all this up, check the reference below...

Thanks to Tim Harrison for suggesting these molecules. Ref: J.G. Duque, et al, J. Phys. Chem. C (2009) 113, 18863.



Diketene

Diketene should really have a hyphen to make it read di-ketene, but without the hyphen it could be pronounced 'dike-tene' - the favourite molecule of lesbian teenagers? Its name in Dutch is 'diketeen', which sounds like 'dikke teen', which means a fat toe!

Thanks to Henk Bosch for suggesting this molecule. Ref: wikipedia.



Carmoterol

This is a drug being developed for asthma treatment by an Italian Pharmaceutical company. The only problem is the name - if you were an asthmatic, would you like to inhale something that sounds like 'car motor oil'?

Thanks to Chris Hall for suggesting this molecule.



Fagomine and Fagarine

Hmm, it's difficult to make any jokes about these molecule names with being very politically incorrect. But we'll do it anyway. :-) Maybe 'fagomine' is how you'd describe a rent-boy to a friend. Since 'fag' in the UK is simply slang for cigarette, saying to someone "would you like a fagomine" is quite innocent. But don't try this in the US... Fagomine was first extracted from buckwheat seeds (Fagopyrum esculentum Moench) and has possible uses to treat diabetic disorders. A related compound with another excellent name, Isofagomine tartrate, is an experimental drug for the treatment of certain forms of Gaucher's disease.
Although sharing a similar-sounding name, fagarine, on the other, hand was extracted from a completely different plant, Argentinian Fagara coco (Rutaceae), and is a potential cardiac drug, although it sounds like a gay figurine.

Thanks to Arnold Martelli for suggesting these molecules. Ref: A. Kato et al., J. Nat. Prod., (1997) 60 312; V. Deulofeu et al., Nature, 162, (1948) 694.



Pikachurin

This is a retinal protein discovered by Japanese researchers in 2008, which was named 'Pikachurin', refering to Pikachu, the mascot of the popular video-games series Pokemon. This name was inspired by the parallel between the protein action ("dystroglycan-interacting protein which has an essential role in the precise interactions between the photoreceptor ribbon synapse and the bipolar dendrites", i.e. it enhances visual acuity), and Pikachu's "lightning-fast moves and shocking electric effects"...

Thanks to Arnaud Demilecamps for suggesting this protein. Ref: S. Sato, et al, Nat. Neurosci. 11 (2008) 923.



Labyrinthopeptins

These are a new type of peptide that are synthesised by bacteria. They gets their name from their apparently complicated, labyrinthine structure, although the structure (right) doesn't look that complex to me. I wouldn't be surprised if someone soon discovers a component to this peptide and calls it minotaurin...

Thanks to Jan Linders for suggesting this molecule. Ref: K. Meindl et al., Ang. Chemie Int. Ed., 49, 1151.



Hangman and Pacman Porphyrins

Pacman molecules are formed by taking two flat, disc-like porphyrin rings and attaching them face-to-face by a stiff bridging linker. The resulting molecule resembles a Pacman from the computer game, and the open cleft between the two porphyrin rings also acts like a 'mouth', gobbling up molecules like oxygen and trapping them in its bite. This process can be reversible, so Pacman porphyrins are being investigated as possible substitutes for haemoglobin. Related to these are Hangman porphyrins, where a small molecule such as -COOH is suspended by a molecular 'gallows' directly above the ring, like a hanged man. The choice of suspended group (shown in red in the structure, right), determines the molecule's ability to reversibly bind O2 and other small species.

Thanks to Jan Linders for suggesting this molecule. Ref: J. Rosenthal, D.G. Nocera, Acc. Chem. Res., 40, (2007) 543.



Retarded acid

Retarded acid is an emulsion formulation used in petroleum and gas production. Although it sounds like it should have the fomula SeN (for Special Educational Needs...), it's composed of a mineral acid (e.g. HCl) capable of dissolving salts out of rocks, an emulsifier (such as an amine salt of dodecylbenzene sulfonic acid, and a corrosion inhibitor. This mixture forms a kind of slow-acting (i.e. 'retarded') strong acid that can penetrate deep into silicate rocks dissolving out the salts and leaving behind channels and percolation pathways through which oil can seep. Faster-acting acids simply react with the rock surface and never get deep enough to dissolve out the salts, which is why they need to be retarded.

Thanks to Jan Linders for suggesting this acid. Ref: C.R. Fast et al., US patent 3681240 (1972).



Bum

Bum is another wonderful abbreviation which stands for the tertiary-Butyloxymethyl group, so the molecule shown in the image is actually Bum-Cl. It doesn't seem to do much except hang off the backside of a peptide, just like a real bum.

Thanks to Neil Allan for suggesting this molecule. Ref: M. Mergler et al., J. Peptide Sci. 7 (2001) 502..




Epibatidine

Phantasmidine

This fantastic, phantasmagorical molecule is not a fantasy, nor a phantom molecule, but a poison from a tiny Amazonian tree frog, Epipedobates anthonyi, which used to be known as the 'Phantasmal poison frog'. It is hoped that this molecule will have similar painkilling effects to the related molecule epibatidene which also occurs in the same frog. The name 'epibatidine' came from the frog Latin name Epipedobates and the fact that it was a diamine, tactfully removing the middle part of the name of the frog (-pedo-) for different connotations in Spanish! This molecule achieved a significant amount of publicity in the popular press when it was first discovered. So much so, that the songwriter, Paul Simon, memorialized it in the song, Senorita With A Necklace of Tears:

Nothing but good news
There is a frog in South America
Whose venom is a cure
For all the suffering that mankind must endure
More powerful than morphine
And soothing as the rain
A frog in South America
Has the antidote for pain.

Thanks to Jan Linders for suggesting these fantastic molecules. Ref: R.W. Fitch et al., J. Nat. Prod. 73 (2010) 331.
H.M. Garraffo, T.F. Spande, M. Williams, Heterocycles, 79, (2009) 207.
P. Simon, 'Senorita with a necklace of tears'. Album: You're The One. Warner Bros Records, 2000, CD 9:47844-5-2.



Papyriferic Acid

This terrific molecule gets its name since it was extracted from the twigs of the juvenile paper birch tree (Betula papynyera ssp. humilis). It's a possible anti-cancer drug which helps with cancers that are multi-drug resistant.

Thanks to Jan Linders for suggesting this terrific molecule. Ref: J. Xiong et al., Bioorg. Med. Chem. 18 (2010) 2964.



Gigantine

This chemical comes in very, very large bottles! It's from the cactus Carnegia gigantea, and is a hallucinogen - so perhaps it just makes everything appear gigantic.

Ref: J.E. Rodgkins, S.D. Brown J.L. Massigill, Tetrahedron Lett. 8 (1967) 1321.



Nudic acid

A molecule for naturists? This is an antibiotic derived from mushrooms, one of which (Tricholomo nudus) was the origin of its name.

Ref: M. Anchel, J. Am. Chem. Soc. 75 (1953) 4621.



Powder of Algaroth

This sounds like one of Harry Potter's wizardly potions, and is the archaic name for antimony oxychloride (SbOCl). It was named after the Italian chemist Vittorio Algarotti who discovered its use as a medical emetic which purges violently both 'upwards' and 'downwards'... Perfect for a party prank, then...



Didymium

Ken Dodd's favourite chemical? This is another old term, this time for a mixture of neodymium and praseodymium, which, due to their similar chemical properties were inseparable for many decades. The name comes from the Greek word for twin (didymos).



Melon

Melon is a flame-retardant chemical. Its name is coined by variation from that of a similar molecule called melem, which got its name from another similar molecule melamine, which got its name from melam, which was just an arbitrary name! Would an aqueous solution of melon be called a water-melon? The picture to the right shows the structure of melon drawn on an actual melon.



Hanuš Reagent

Dudes, this reagent is, like, totally heinous! It's, like, a totally equimolar mixture of iodine and bromine in glacial acetic acid, named after the most excellent, and definitely non-heinous Czech chemist Josef Hanuš. It's used to measure the unsaturation (number of double bonds) in organic substances. Radical!



Strawberry Aldehyde

This molecule's proper name is ethyl methylphenylglycidate and is used in the food industry as artificial stawberry flavour. Despite its common name of strawberry aldehyde, it's not an aldehyde, being classified as an ester and epoxide, and it doesn't come from strawberries, although it does taste of them.



Fluorene and Theobromine

Fluorene is an unusual name in that the molecule doesn't contain the element fluorine! It gets its name from the fact it fluoresces under UV light. Similarly, theobromine doesn't contain any bromine. It's derived from cocoa trees (Theobroma), and is the bitter taste in dark chocolate. Theos actually means 'god' in Greek, and broma means 'food'. So, chocolate really is the food of the gods!


Fluorene


Theobromine



Dodoneine

No, this isn't an extinct molecule. It gets its name since it was isolated from Tapinanthus dodoneinfolius, a parasitic plant that feeds from the sheanut tree in Burkina Faso (West Africa).

Thanks to Jan Linders for suggesting this not-so extinct molecule. Ref: F. Allais and P.-H. Ducrot, Synthesis (2010)..



Coffinite

This mineral has a very appropriate name, considering it's a silicate uranium ore that's highly radioactive. It's named after the American geologist Reuben Clare Coffin. I wonder if this mineral would react well with the sarcophagene or sepulchrate molecules mentioned earlier?


Coffinite - Dracula's favourite mineral?



Cyclopamine

This is definitely a molecule to keep your eye on! In the middle of the 20th century, lambs in sheep herds in Idaho began to be born with severe craniofacial defects; some even had cyclopia — the existence of only one eye placed directly on the forehead. This ailment is named after the Cyclops in Homer's Odyssea. It was discovered that in times of drought the sheep moved to higher grounds and grazed on the flower veratrum californicum. This flower was later shown to contain three compounds which caused the sheep to have cyclopia; one of these was named cyclopamine.

Thanks to Jan Linders for suggesting this not-so extinct molecule. Ref: P. Heretsch et al., Angew. Chemie Int. Ed. 49 (2010).



Chavicine

For non-UK readers, 'chav' is a British slang term for a subcultural stereotype of a youth who's fixated on fashions such as imitation gold, poorly made jewellery and fake designer clothing, combined with elements of working-class British street fashion, such as trainers, tracksuit bottoms and polo shirts. It's not certain what, if anything, 'chav' stands for, but one popular intepretation is 'Council House And Violent'. Chavicine sounds like an ideal molecule for them, since it's the hot, sharp flavour found in black pepper - perfect to put on a late night pizza or kebab on the way home from the pub. Innit?

Ref: R. De Cleyn, M. Verzele, Chromatographia 5 (1972 346).



Carbuncle

This mineral has got nothing to do with skin lesions or sores, except for the red colour. It's an old term that used to refer to any fiery red mineral, but nowadays is restricted to red garnets such as pyrope.


A pyrope gem, certainly not a carbuncle!



Tamuic acid

Tamuic acid is a shorthand term for an organic acid with a huge unwieldy name that's used as a ligand in organometallic chemistry. The name comes from the place it was discovered, Texas A&M University. The related molecule with 4 C=C units was named by the same group texic acid (after Texas). On the same theme, there's also tuftsin, a tetrapeptide named after Tufts University in Boston where it was discovered. If the trend continues, let's hope that Cambridge University Nano-Technology centre don't discover a molecule soon!

Ref: F.A. Cotton, J.P. Donahue, C.A. Murillo, J. Am. Chem. Soc. 125 (2003) 5436.




Ah'm in a fight...
...Ah'm in a fight, too.

Aminoffite

A boxer's favourite mineral? This mineral has formula Ca3Be2(Si3O10)(OH)2 and forms clear pyramidal crystals. It's named after the Swedish Mineralogist Gregori Aminoff.



Bionic acids

I wonder if these cost six million dollars each and give you super strength? Actually, there are a number of bionic acids which are derived from cellobiose, which is a sugar digestion product of cellulose. The differences come from the component sugars which make up the reduced form, and include maltobionic, melibionic, cellobionic, aldobionic and lactobionic acid (the one shown here).



Wanklyn's Soap

No doubt Wanklyn's soap is used a lot by teenaged boys! According to the label it's flammable and has one degree of hardness! Wanklyn's Soap is an ethanolic solution of soap which was formerly used to test for water hardness, and formed the basis of the Wanklyn Scale of hardness.

Thanks to Stephen Ashworth of UEA for suggesting this molecule.



Miraculin

Miraculin is a glycoprotein extracted from the West African 'miracle fruit' shrub. Miraculin itself is not sweet, but, once exposed to miraculin, human tastebuds perceive ordinarily sour foods, such as citrus, as sweet for up to an hour afterwards. Because the miracle fruit itself has no distinct taste, this taste-modifying function of the fruit had been regarded as a miracle - hence the name of the shrub.

Ref: S. Theerasilp, H. Hitotsuya, S. Nakajo, K. Nakaja, Y. Nakamura, J. Biol. Chem. 264 (1989) 6655.


The red berries of the miracle fruit with, below,
the listing of the amino acid residues of miraculin.



Gonadoliberin

This name sounds like this protein makes a guy's most-valued possessions drop off. In fact it's a hormone that is involved in controlling the reproductive cycle of many creatures, including humans.



Splendipherin

This splendidly named protein is a sex attractant pheromone used by the Australian 'Magnificent tree frog' (Litoria Splendida), and was the first pheromone ever to be found in frogs. It comprises 25 amino acid residues, and is water soluble. It's exuded by male frogs who use it to attract females. Splendid!

Ref: P.A. Wabnitz, J.H. Bowie, J.C. Wallace, M.J. Tyler, B.P. Smith, Nature 401 (1999) 444.


Magnificent Tree Frog, and the amino acid sequence of its splendiferous pheromone.




Structure of carlsbergite.

Carlsbergite

Is this (probably) the best mineral in the world? This mineral was named after the Carlsberg Foundation of Copenhagen, Denmark (yes, the same one that makes the beer), which supported the recovery and cutting of the Agpalilik meteorite wherein it was discovered. On the same theme, there's a nickel-sulfide mineral called millerite, which isn't to be confused with Miller-lite, the beer


Oh, I thought you said a Carlsberg Lite?



Crosbyanols

These sound like they should be part of a music group - all we need are the Stills, Nash and Young derivatives to get the full set. In fact crosbyanols are antibiotics derived from the marine cyanobacterium Leptolyngbya crossbyana. This periodically forms extensive blooms on Hawaiian coral reefs and results in significant damage to the underlying corals. There are different versions of crosbyanol, A-D, depending on whether the yellow H's in the structure (shown right) are replaced by other groups such as sulfates.

Thanks to Jan Linders for suggesting this musical molecule. Ref: H. Choi et al., J. Nat. Prod. 73 (2010) 517.


Crosby, Stills, Nash and Young... and crosbyanol A.



Baptisin

A molecule for religious types? It's called this because it's extracted from the wild indigo plant (Baptisia tinctoria). It's sometimes used in herbal medicine as an emetic.

Thanks to J.J. Keating from University College Cork for the details of this molecule.



Hymenin

A molecule for chemistry virgins? Hymenin is a novel bromine-containing alkaloid which was isolated from the Okinawan marine sponge Hymeniacidon sp.

Ref: J. Kobayashi et al, Experientia 42 (1986) 1064.



Lovastatin

Lovastatin is a statin, a class of drugs used for lowering cholesterol in the blood and so helping to prevent heart attacks. It occurs naturally in food such as oyster mushrooms. I don't know why it's called lovastatin - maybe there's a connection with the supposed aphrodisiac properties of oysters?

Thanks to Neil Brew for the details of this molecule. Ref: Wikipedia



Silver FOX

The high-explosive molecule 1,1,-diamino-2,2-dinitroethene often goes by the abbreviation FOX-7, since it was the shortened version of 'FOI Explosive (FOX) number 7'. It was the seventh in a series of new explosives developed by the Swedish Defence Research Agency (FOI, from the full Swedish name Totalförsvarets forskningsinstitut), a name that raises a few eyebrows in English! Reacting FOX-7 with silver produces Silver-Fox, which, as fans of the Marvel comic X-men will know, was a superheroine/villain and a lover of Wolverine.

Thanks to Andrew Byro for this molecule and to Rob Schmidt for the origin of its name. Ref: S. Garg, et al., J. Am. Chem. Soc. (2010).



Enigmazole

This molecule is a bit of a puzzle... Actually it's easily solved - the name comes from the fact it's extracted from the sea sponge Cinachyrella enigmatica. It's involved in cell reproduction and has been implicated in some forms of cell mutation.

Thanks to Jan Linders for this molecule. Ref: C.K. Skepper, et al., J. Am. Chem. Soc. (2010).



Onionin

As you might suspect, onionin is the ingenious name given to a new molecule extracted from, duh, onions, Allium cepa to be precise. It's a sulfur-contining compound which may have tumor suppressing qualities. The preparation method taken from the paper below sounds a bit like a cooking recipe: take a few large onions, roughly chop them, and then put them into a blender with some acetone, and blend into a puree. Leave to soak for 3 days at room temperature before filtering.

Thanks to Jan Linders for this molecule. Ref: M. El-Aasr, et al., J. Nat. Prod. (2010).



Queuine

It seems that vowels are just queueing up to be in this molecule. This molecule has 4 vowels in a row - is the longest uninterrupted row of vowels in a chemical name? And this begs the question...what is the longest uninterrupted row of consonants in a chemical name? I don't know how queuine got its name, but it occurs in the 'wobble' position of four tRNAs.

Thanks to Jan Linders for this molecule. Ref: A.F. Brookes, et al., Tet. Lett. 51 (2010) 4163.



FucM

This wonderfully named gene is short for the 'mammalian fucose mutarotase gene'. The FucM enzyme made by this gene is is known to be involved in incorporating the sugar fucose into protein. It seems that female mice that lack the FucM gene refuse to let males mount them, and will attempt copulation with other female mice. FucM indeed!

Thanks to Charles Turner for suggesting this molecule. Ref: D. park, et al., BMC Genetics. 11 (2010) 62.



Nanoguitar

Ok, so it's not strictly a molecule, but I thought I'd include it since we have a lot of other silly nano-things here already. A few years ago researchers at Cornell University made the world's smallest guitar, about the size of a red-blood cell, to demonstrate the possibility of manufacturing tiny mechanical devices using techniques originally designed for building microelectronic circuits. They've recently made a slightly larger one, modelled on a Gibson Flying 'V' that's actually playable. A laser is used to pluck the strings which vibrate at frequencies 17 octaves higher than those of a real guitar, or about 130,000 times higher pitch. These guys cetainly know how to Rock!

Thanks to Andrew Byro for suggesting this molecule. Ref: Cornell News 2003



Destruxin

Destruxins are anti-cancer agents that were isolated for the first time in the early 60s from the bacteria Mefarhizium anisopliae which was formerely known as Oospora destructor in Japan, hence the name. They were noted because of their toxic effects on silkworms. There are different destruxins labelled A, B, C, etc depending on changes in the various sidegroups.

Thanks to Jan Linders for suggesting this molecule. Ref: M. Yoshida, et al., Org. Letts. (2010); Y. Kodaira, Agric. Biol. Chem., 26, (1962) 36.



Kisspeptin

Kisspeptins are the peptide products of the KiSS-1 gene, and unsurprisingly, play an important role in puberty, reproduction and reproductive development. The KiSS gene itself was named since it was discovered in a laboratory in Hershey, Pennsylvania, home town of the well-known chocolate company whose most famous product is Hershey's Kisses.

Thanks to Rob Towart for suggesting this molecule. Ref: S. Messager, et al, PNAS., 102, (2005) 1761.



Moolooite

Moolooite is not a cow's favourite mineral. It's a rare blue-green mineral formed from hydrated copper oxalate, which is created by the interaction of bird guano with weathering copper sulfides! Its name comes from the location where it was found, Mooloo Downs station, Murchison, Western Australia. A small piece of moolooite is shown in the bottom left-hand side of the photo.

Thanks to Derek Belknap for suggesting this mineral.

A cow and some moolooite


Queen Beatrix of the Netherlands

Koninginin

Although it may not mean much to English speakers, Koningin in Dutch means 'Queen'. This molecule gets its name since it was first isolated from a culture of the fungus Trichoderma koningii. The picture (right) is, appropriately, of Queen Beatrix of the Netherlands, and her queenly molecule.

Thanks to Jan Linders for suggesting this molecule. Ref: G. Liu and Z. Wang, Chem. Comm., (1999) 1129.



A taco

Taconite

Taconite is not a celebration night of partying that involves eating lots of tacos, nor is it a mineral made from minced meat wrapped in tortilla. In fact it's a type of hard, silica-rich iron-ore (photo, right) found in the Lake Superior region of the USA. It got its name because the geologist who discovered it (Newton Horace Winchell) thought it resembled the iron-bearing rocks he'd seen in the Taconic Mountains of New York.

Thanks to Derek Belknap for suggesting this tasty-sounding mineral.

Photo of Taconite


Zippeite

Zippeite

Zippeite sounds like it's named after the children's TV character Zippy from Rainbow (a 1970's program in the UK), and at first sight is almost the same colour! It's actually a hydrous potassium uranium sulfate mineral which forms efflorescent encrustations in underground uranium mines. It was named after the Prague minerologist, F.X.M. Zippe (1791-1863).

Thanks to Derek Belknap for suggesting this mineral.

Zippy


obtusenyne or an obtuse-9, geddit? - click for 3D structure

Obtusenyne

This sounds like an extremely italicised number 9, i.e. one which has an obtuse angle. It's actually a nine-membered ring isolated from Laurencia obtusa, a red algae found in the Aegean sea.

Thanks to Jan Linders for suggesting this mineral. Ref: M.T. Crimmins and M.T. Powell, JACS, 125, (2003) 7592.



Conduritol

This is another one for the French speakers. In French this sounds like con du Ritol, which translates roughly as 'Ritol's idiot'. But as well as 'idiot', con in French, can also be a very rude term for female genitalia. So, another, more vulgar translation is 'Ritol's c**t'. There are six isomers of conduritol, the first of which was isolated in 1908 from the bark of the vine Marsdenia condurango, hence its name.

Thanks to Marc Schaefer for suggesting this molecule.

Conduritol - click for 3D structure


Hemp

This is an acronym for a protein found in mammals called hematopoietic expressed mammalian polycomb which plays a role in development of stem cells. At least now we have conclusive proof that medical students experiment with using hemp...

Thanks to Jan Linders for suggesting this protein. Ref: H. Hondaa, et al, PNAS, 108, (2011) 2468.

HEMP - with part of the structure of the Hemp protein overlaid.


A real bivalve

Bivalvane

This molecule is a half-finished version of dodecahedrane, before the 2 halves are fused together. Because of the striking physical similarity of this molecule to that group of mollusks having dorsally hinged lateral shells (clams, oysters, etc.), it was named bivalvane, although strictly is should be pentasecododecahedrane.

Thanks to David Fairley for suggesting this molecule. Ref: L.A. Paquette, I. Itoh, W.B. Farnhaml, JACS, 97, (1975) 7280.

Bivalvane structure


Saucerneol

This molecule is extracted from the plant Lizard's Tail (Saururus cernuus), hence its name. It hasn't found many applications yet, although maybe it could be used as the fuel source for flying saucers?

Thanks to Jan Linders for suggesting this molecule. Ref: K.V. Rao and F.M. Alvarez, Tet. Letts., 24, (1983) 4947.

A flying saucer


Wee1

This is a protein found in a cell nucleus, and despite its name it has nothing to do with removing excess water from the cell. Its name comes from the Scottish term 'wee' meaning small, because its discoverer, Paul Nurse, was working at the University of Edinburgh at the time of discovery. Wee1 is a key regulator of cell cycle progression, and it influences cell size by preventing the cell dividing. There are also molecules called 'Wee1 inhibitors', which stop Wee1 working properly. Apparently, they have nothing to do with preventing urination, or of stopping pregnancy (stops wee ones!), or for the Dutch speakers - labour pains ('wee' in Dutch = labour pain).

Thanks to Jan Linders for suggesting this molecule.

Wee1


Celine-dion holding her molecule

Selene Dione

No, the canadian singer Celine Dion hasn't got a molecule named after her. This is the trival name for diselenoacetylacetone which is a reagent used for the separation of metal ions.

Thanks to Jan Linders for suggesting this molecule. Ref: T. Honjo, Fresenius Z. Anal. Chem. 327 (1987) 798.



Cloverite

Cloverite

Is this the world's luckiest molecule? This is a zeolite-like cage structure made from gallium and phosphate, which has a large opening through the middle which resembles a 4-leafed clover - hence the name. It has potential uses in shape-selective adsorption, and maybe petroleum cracking, but only if you're lucky.

Thanks to David fairly for suggesting this molecule. Ref: R. L. Bedard, et al, J. Am. Chem. Soc, 115, (1993) 2300.

A 4-leaf clover


Copulins

Copulins are the name given to a group of fatty acids and compounds secreted by females which act as sex pheromones to attract male partners. The word was coined by researcher Richard Michael in 1971. He claimed to have pinpointed compounds in the vaginal secretions of rhesus monkeys, that when sniffed, caused the male monkeys to initiate sex. These compounds were called copulins, although their exact chemical structure was never identified. Critics at the time pointed out that the evidence for these compounds was scarse - only 2 of the male monkeys accounted for 50% of all the data! Nevertheless, the idea of a human pheromone took hold, despite the lack of evidence for there being one - and now you can buy 'copulins' on the internet with promises of becoming 'instantly sexually attractive', although no-one will tell you what's actually in the bottle, and what, if any, evidence exists that they work. Although Kermit seems to be doing ok in the picture on the right...

Thanks to David Fairley for suggesting these molecules. Ref: Bonk by Mark Roach: ISBN: 978-0-393-06464-3. pp288-291.

Even a frog might get lucky...


Trianglamine

I think the chemists who named this molecule had very little imagination. It's triangle-shaped, and an amine, I know, let's call it trianglamine! Maybe it could be the smallest musical instrument in a nano-orchestra! It's used mainly as a chiral reagent for steroespecific synthesis of alcohols.

Thanks to Jan Linders for suggesting this molecule. Ref: A. Gualandi et al, Org. Biomol. Chem. 9 (2011) 4234.

Trianglamine


Drunk guy

Merrilactone

The happiest chemical in the world? Or just one for merry-making? I would have thought that to make people merry it would have been an alcohol rather than a lactone... This happy molecule gets its name from a small Japanese tree called Illicium merrillianum and has possible uses in treating nerve diseases.

Thanks to Jan Linders for suggesting this molecule. Ref: L. Shei, K. Meyer and M.F. Greaney, Angew. Chem. Int. Ed. 49 (2010) 9250.

Merrilactone


Vaticanol

The pope's favourite molecule? However, it's got nothing to do with the Vatican - it gets its name because it was isolated from the bark stem of the vatica rassak tree. It is currently being investigated for its anti-cancer properties - maybe it'll provide miraculous cures?

Thanks to Jan Linders for suggesting this molecule. Ref: Tanaka et al., Phytochem. 54 (2000) 63.

vaticanol


Maoecrystal

And here's another world leader. They don't say for sure, but the Chinese group who managed to isolate this molecule from a Chinese medicinal herb probably named it maoecrystal after Chairman Mao. They also named another molecule extracted from the same plant xingdongnin, maybe after a famous Chinese person called Xing Dong? Anyone know? Either way, I think it should be called the door-bell molecule (Xing dong...).

Thanks to Jan Linders for suggesting these molecule. Ref: Maoecrystal: Shen et al., Phytochem. 35 (1994) 725; Xingdongnin: Han et al, Tet. Lett., 45 (2004) 2833.

Maoecrystal V Chairman Mao xingdongnin M


Loline

Does this molecule make you LOL? Or if it's cooled down does it become an ice-loline? In any case, it's an alkaloid which is produced in grasses (particularly Lolium arundinaceum, hence the name) that are infected with certain types of fungus, and acts as an insecticide.

Thanks to Jan Linders for suggesting this molecule. Ref: Wikipedia.

Loline


MAD - click for a 3D MAD experience

MAD

Here's a molecule with a totally crazy acronym. MAD is short for methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide), which is a monomeric aluminium compound that is used as a reagent in organic reactions. Maybe this one is only for mad scientists...

Thanks to Patrick Stewart for suggesting this molecule. Ref: See here.



Tormentic Acid

...and this one is for tormented souls? It gets its name, not from its tormented structure or from its effects upon users, but simply because it can be isolated from tormentil, a yellow flower of the rose family.

Thanks to Jan Linders for suggesting this tormented molecule.

tormentic acid


Photo of a balloon

HOTAIR and HOTS

HOTAIR is a gene which is responsible for changing the type of skin found at different parts of the body, e.g. the skin of the eyelid differs quite a bit from that on the sole of the foot. Its name comes from HOX antisense intergenic RNA (with an extra 't' added). HOX is a type of gene that regulates how the body develops, 'antisense' is the name given to one of the strands of DNA (or RNA), and intergenic means a part of the DNA (or RNA) strand that contains few or no genes. A related gene, called HOTS (from H19 opposite tumor suppressor), is thought to help prevent tumour growth. So it appears to be quite healthy to have the HOTS.

Thanks to Jan Linders for suggesting these HOT molecules. Ref: http://en.wikipedia.org/wiki/HOTAIR. Ref: P. Onyango and A.P. Feinberg, PNAS 108 (2011) 16759.



A dog doing a cac-alone..?

Cacalone

This is a wonderfully named molecule that sounds like someone is taking a poo by themselves. In fact its name, and that of a closely related molecule, cacalol, arise from the plant from which it was originally derived. Cacafea decomposita is a shrub widely distributed in the northern part of Mexico popularly known as 'matarique' and 'matufin'. Extracts from its roots have been used by the natives for the treatment of diabetes and other diseases for many generations.

Thanks to Jan Linders for suggesting this molecule. Ref: Ref: M. Jimenez-Estrada et al, J. Ethnopharm. 105 (2006) 34.

CacaloneCacalol


psychotripine

Psychotripine

This sounds like a hippy's favourite molecule. It's an alkaloid derived from the plant Psychotria pilifera, hence the name. Despite its trippy name, it doesn't appear to have any hallucinatory effects, nor any medicinal value, and the only unusual thing about it is that its structure contains 11 conjoined rings...unless I've hallucinated that...

Thanks to Jan Linders for suggesting this molecule. Ref: X.-N. Li et al, Org. Letts. (2011).



Diffractaic Acid

This acid didn't get its name due its diffraction pattern, but because it was derived from a lichen named Parmelia diffractaica. It is a type of compound called a depside, which have antibiotic, anti-HIV, antioxidant, and which are potent non-steroidal anti-inflammatories. A slight modification to its structure (replacing the blue methyl group with an H) gives another depside with another strange name: barbatic acid.

Thanks to Jan Linders for suggesting this molecule. Ref: S. Kumar KC and K. Muller et al, Eur. J. Med. Chem. 34 (1999) 1035-1042.

Diffractaic acid - click for 3D structure


A molecule named Joe...

JOE

Here's a molecule simply named JOE! It's a fluorescent dye that's used to label DNA and other proteins so they can be detected in assays. It's full chemical name is 4'-5'-Dichloro-2',7'-dimethoxy-5(6)-carboxyfluorescein. I have yet to find out why it's named JOE, since there's nothing in its chemical name that could be abbreviated to this. Anyone know?

Thanks to Jan Linders for suggesting this molecule. Ref: D.A. Tsybulsky et al, J. Org. Chem. 77 (2012) 977.



Madindoline

What's so mad about this indoline? It was originally extracted from a micro-organism (Streptomyces nitrosporeus), but for some unknown reason the organism then decided not to make it any more (stroppy microbe?), so purely lab synthetic methods needed to be developed. It has potential anti-cancer properties. The only reason I can find for it being called 'mad'-indoline is that the bacterium the compound was isolated from was itself isolated from soil samples from Madison, Wisconsin.

Thanks to Jan Linders for suggesting this molecule, and to Bastiaan Vos for finding out why it's called 'mad'. Ref: L. Wan et al, Org. Lett. 9 (2007) 647.

Mad, mad, mad


Rigidiusculamide A - click for 3D structure

Rigidiusculamide

This stiff-sounding molecule sounds like the name of a comedy Roman centurian - Rigidius Culamide, perhaps the son of Biggus Dickus and Incontentia Buttocks from Monty Python's The Life of Brian? Its name arises because it was first isolated from the crude extract of the fungus Albonectria rigidiuscula. It might have uses as an antibacterial antibiotic drug.

Thanks to Jan Linders for suggesting this molecule. Ref: G.-Y. Chen et al, Chem. Asian J. (2012), doi: 10.1002/asia.201100809.



Christite

This mineral isn't particulary porous, although you might think it should be with such a holy name (geddit?). Maybe it's the rock that stone crucifixes are sculpted from? In fact it is a rare mineral with formula TlHgAsS3 with a bright blood-(?) red colour. It's named after the American mineralogist Dr. Charles L. Christ (strange,...I always thought his first names were Jesus H.?).

Thanks to Mark Morey for suggesting this holy mineral. Ref: http://webmineral.com/data/Christite.shtml.

Structure of christite


Stattic, the molecule, on static, the TV

Stattic

This molecule comes as a bit of a shock! However, it doesn't get its name from static electricity, nor from its lack of movement. Its name comes from STAT three inhibitory compound, although its proper name is 6-nitrobenzo[b]thiophene 1,1-dioxide. STAT-3 is one of a family of STAT biomolecules (Signal transducers and activators of transcription) which transmit signals from the cell membrane to the nucleus. STAT-3 is linked to various cancers, so a molecule which can inhibit its action, such as stattic, has potentially anti-cancer properties.

Thanks to Jan Linders for suggesting this molecule. Ref: J.S. McMurray, Chem and Biol, 13 (2006) 1123.

Static electricity


Shrek

Schrekstoff

This substance is not quite as scary as the ogre, Shrek, but nearly so, because Schrekstoff quite literally means 'scary stuff' in German. It's an alarm chemical that fish release when they've been injured to warn other fish of potential danger. Schrekstoff itself is a mixture of various molecules, but the main active ingredient is chondroitin sulfate (shown in the diagram) which is a sulfonated linear, heterogeneous polymer made of disaccharides.

Another molecule that was alledged to evoke fear was scotophobin, named after scotophobia (fear of the dark) from the Greek for 'darkness'. In one experiment, rats, normally nocturnal animals, were conditioned to fear the dark and scotophobin was supposedly extracted from the rats' brains, and was claimed to be the molecule responsible for the rats remembering this fear. However, these findings were subsequently debunked, so scotophobin doesn't actually exist!

Thanks to Jan Linders for suggesting this molecule. Ref: A.S. Mathuru et al., Curr. Biol. 22 (2012) 1.

Chondroitin sulfate structure


A BIG molecule

BIG

The proper name for BIG is suitably large - bis(1-methylimidazol-2-yl)glyoxal. It's a chelating agent that bonds to various transition metals, and may help in catalysis or asymmetric synthesis.

Thanks to Patrick Stewart for suggesting this molecule. Ref: O. Sarper et al., Inorg. Chem. Acta 363 (2010) 3070.

Now that's BIG!


Harry Potter's basilisk...

Basiliskamide

This scary sounding molecule has nothing to do with lizards, or Harry Potter's huge snake! It's a molecule that shows potential anti-bacterial properties, which is ironic since it was first extracted from another bacterium (PNG-276) found in the waters of a tropical island, close to Papua New Guinea. This island, Loloata, has also given its name to another batch of antibiotic molecules, the loloatins. Basiliskamide was apparently named after marine geographic features in the region of this island, which I suppsoe means there was an underwater rock formation that the locals call Basilisk rock?

Thanks to Jan Linders for suggesting this molecule. Ref: T. Barsby, M.T. Kelly, R.J. Andersen, J. Nat. Prod.. 65 (2002) 1447.

...and the molecule, basiliskamide.  Click for 3D structure.


The Flash

FlAsH

The shorthand name for 4',5'-bis(1,3,2-dithioarsolan-2-yl)fuorescein, FlAsH, is particular appropriate, as this molecule is used to bind to proteins to tag them. When exposed to UV light, the molecule then fluoresces (flashes!), identifying where the labelled protein is in the cell.

Thanks to Patrick Stewart for suggesting this molecule. Ref: H. Yang et al., Bioconj. Chem. 21 (2010) 1341.

FLASH!


Bogorol, the molecule

Bogorol

This is another antibiotic molecule extracted from the same bacterium as basiliskamide, above. I have no idea why it's called bogorol, though. Maybe the scientists ran out of toilet paper on their diving expedition and needed an absorbent molecule...

Ref: T. Barsby, et al, Org. Lett.. 3 (2001) 437.

Bogroll, the bog-roll


NOSH compounds

Despite their name, NOSH compounds aren't particularly good to eat, as they are derivatives of aspirin. Their names comes from the nitric acid (NO) and hydrogen sulfide (H2S) releasing mioeties that have been attached to the aspirin backbone. They are far more potent than standard aspirin, and have anti-cancer properties.

Thanks to Jan Linders for suggesting this molecule. Ref: R. Kodela et al, ACS Med. Chem Lett.. 3 (2012) 257.

NOSH1 - click for 3D structure


Stampidine structure

Stampidine

This molecule has nothing to do with the Penny Black, but it does stamp its authority as it's an anti-HIV drug.

Thanks to Jan Linders for suggesting this molecule. Ref: wikipedia.

Stamp out the structure...


Babe - the pig

BABE

This molecule wasn't named for its good looks, or for its resemblance to a film pig. It's actually an acronym of bromo-acetylamidobenzyl-EDTA, where EDTA itself (the blue part of the structure, right) is short for ethylenediamine tetraacetic acid. BABE is a chelating agent that can be used to bind to proteins, labelling them for subsequent separation and diagnosis.

Thanks to Patrick Stewart for suggesting this molecule.

BABE


Navelbine structure

Navelbine

Nothing to do with bellybuttons...Navelbine is actually the tradename of the drug Vinorelbine, which is a type of anti-cancer treatment. Vinorelbine gets its name because it was obtained by semi-synthesis from alkaloids extracted from the rosy periwinkle flower (now called Catharanthus roseus) whose previous Latin name was Vinca rosea. But why the French scientists at the CNRS who discovered it decided to market it under the name navelbine is anyone's guess. Maybe they were just navel-gazing, or maybe they thought that if it was named 'vin-' the other French researchers might confuse it with wine...

Thanks to Jan Linders for suggesting this molecule. Ref: Wikipedia



Homoeriodictyol

This wonderfully named molecule has a name with so many potential double entendres that it seems like it's been made up deliberately. But it actually gets its name from the fact that is extracted from the American plant Herba Santa (Eriodictyon californicum). Apparently it's used as a taste modifier to mask bitter flavours, such as those in some drugs like paracetamol and quinine. So, next time you swallow something bitter, ask your pharmacist for some sweet homoeriodictyol...

Thanks to Melanie Wagner for suggesting this molecule. Ref: Wikipedia

Homoeriodictyol


pizda structure

Pizda

Although in English, this name might not seem funny, in the Slavic-languages (Russian, Romanian, etc) this is just about as vulgar as a word can be. In those languages it literally means 'vulva' (or, more accurately, c*nt) and is often used as an insult for someone you don't like. It has gained a lot of publicity and notoriety recently in Russia, particularly because the use of 'obscene language' in official documents or the media is banned there. It's a shorthand for 1-(2"-hydroxyl cyclohexyl)-3-[didecyldimethylammonium]-4-[3'-didecyldimethylammonium] piperazine, and it's believed that a bunch of Iranian chemists came up with the shortened name. I wonder if any of them spoke Russian and knew what 'pizda' meant? As you might imagine, Russian chemistry students have had a field day with this molecule, with questions appearing on the net such as: 'What does pizda taste like?', and 'Does pizda increase in volume when wet?', and 'If you probe pizda with a laser beam does it get excited?'.

Thanks to Krsto Herenda for suggesting this molecule. Ref: Wikipedia



Longdaysin

When scientists discovered a molecule that affected the circadian rhythm in mammals, and in fact lengthened the animal's day period, they of course named it longdaysin. The more longdaysin that's administered, the longer the animal's circadian day period became. This might be used in therapeutic treatments of insomnia or jet-lag. I assume the hunt is now on for the molecule that shortens the period...shortdaysin?

Thanks to Jan Linders for suggesting this molecule. Ref: T. Hirota, et al., PLoS Biol. 8 (2010) e1000559.

Baby yawning - click for 3D structure of longdaysin


Obscurine

Obscurine

This molecule is decidedly obscure... It gets its name because it was first isolated from the equally obscure marine organism Lycopodium obscurum L. It's only a minor alkloid, so its uses are also a bit obscure. There are actually 3 obscurines, the one shown in the picture is alpha-obscurine, with beta-obscurine having an extra double-bond in the lower ring. Just to confuse things completely, a group from Cameroon decided to call their newly discovered molecule obscurine too (because they got theirs from the tropical tree Beilschmiedia obscura), although they may well have to rename it to prevent conflict.

Thanks to Jan Linders for suggesting this molecule. Ref: W.A. Ayer, et al., Tetrahedron. 18 (1962) 567.



A dog's bum

Rimadog

This is a big marketing mistake by Pfizer. Their new non-steroidal anti-inflammatory for dogs, called rimadyl (or carprofen) was originally marketed under the name Rimadog. Pfizer even had an online marketing campaign that invited consumers to Rim-a-Dog! They even have their own URL (rimadog.com) which redirects you to the official site. A spokesman for Pfizer said: "We recently learned that an unintended – and unfortunate – definition has been connected to the RimaDog moniker. We regret if anyone was offended." Yeah, right! I bet someone at Pfizer knew exactly what rim-a-dog meant and tried to see if the senior management would pass it...which they did!

Thanks to Jan Linders for suggesting this molecule. Ref: http://www.pharmalot.com/2012/07/rim-a-dog-pfizer-extends-an-invitation/

Rimadyl


Lubiprotone

Lubiprostone

This is a drug used to remedy constipation and has the tradename Amitiza. The ester derivative of this would probably be called 'lubiprostate', which sounds like it could also be a description of the procedures necessary to cure constipation...

Thanks to Jan Linders for suggesting this molecule. Ref: Lubiprostone website, Wikipedia



Z8E2w-undecaprenol

Z,Z,Z,Z,Z,Z,Z,Z,E,E,ω-Undecaprenol

Surely there must be a limit to the number of Z's there can be in a molecule name? As any chemist knows, the Z refers to the cis-isomer of a double-bonded structure, and every double bond can be either Z (cis) or E (trans). This particular molecule has 8 cis and 2 trans bonds, leading to the very long formal name. With so many Z's it looks like the sleepiest molecule in the world. In theory one could keep extending the chain length indefintely, ensuring that every double bond was cis, resulting in a molecule name with dozens, or hundreds, or Z's. Now that really would be zilly.

Thanks to Jan Linders for suggesting this molecule. Ref: D. Hesek et al, JACS (2012) (dx.doi.org/10.1021/ja306184m).

Sleepy


Barbital

Barbital

This molecule has nothing to do with Barbi-dolls. It's actually a well known sleeping pill and forms part of the barbiturate family, which get their name(s) from being derivatives of barbituric acid (malonyl urea). Barbituric acid was discovered in December 4, 1864, which is the feast of Saint Barbara, and the newly discovered molecule was name in honour of her. So, in a way, barbital is related to Barbi after all - St Barbi!

Thanks to Jan Linders for suggesting this molecule. Ref: Wikipedia.



Fukutin

This unfortunately named protein isn't the result of an expletive uttered by a frustrated biochemist. It's named after the Japanese city of Fukuyama, which also gave it's name to a type of inherited muscular dystrophy first found in that area. Mutations in this protein are thought to be responsible for causing this illness, and so it was named fukutin.

Thanks to Jan Linders for suggesting this molecule. Ref: Wikipedia, and Kuchta et al, Nucl. Acids Res. (2009) [doi: 10.1093/nar/gkp854].

Fukutin


Matrimony

Matrimony

This protein inhibits the processes occurring during the cell division responsible for making egg cells for reproduction. In females (including humans), egg cells can remain dormant for years or even decades as a result of Matrimony inhibiting their development. However, following a chemical trigger, Matrimony is destroyed, and the egg cells can mature and be released ready for fertilisation. So, contrary to popular custom, it is best to conceive a child out of matrimony...

Thanks to Jan Linders for suggesting this molecule. Ref: S. Kendall Smith et al, Cell Cycle 7:6, (2008) 698.



An arm with triceps

TRICEPS

A molecule with muscle? This molecule has been specially created to have 3 reactive sites to allow identification of the different parts of proteins and cells: one that binds ligands containing an amino group, a second that binds glycosylated receptors on living cells, and a biotin tag for purifying the receptor peptides for identification by quantitative mass spectrometry. The name is derived from trifunctional chemoproteomic reagents. Why hasn't anyone made one with only functional moieties so it can be called BICEPS?

Thanks to Jan Linders for suggesting this molecule. Ref: A.P. Frei et al, Nature Biotech (2012).

TRICEPS



Paul Cezanne

Cezanne

Nothing to do with the artist of the same name, this is another protein with a name constructed from an acronym. It stands for cellular zinc finger anti-NF-kB, and is a protein which regulates the inflammatory response in cells.

Thanks to Jan Linders for suggesting this protein. Ref: P.C Evans et al, Biochem. J. 357, (2001) 617.



Parasiticein

Despite its name, this protein isn't a parasite nor is it made of plasticine. It's actually a necrotic compound which causes cell death in the leaves of certain plants, such as tobacco plants. It gets its name from the plant Phytophthora parasitica from which it was first extracted.

Thanks to Victoria Ludowici for suggesting this protein. Ref: C. Nespoulous et al, Planta 186, (1992) 551.



Polydatin

A parrot having a romantic meal? Or someone going on a date with more than one other person at once? Or, more likely, a molecule found in grape juice. Its other name is trans-piceid, since it can be found in the bark of the Picea sitchensis tree. The name polydatin probably originates from the fact that it can be extracted from the root of the Chinese Polygonum cuspidatum herb (but why the '-datin' suffix?). It is used in China as a medicine to treat various cardiovascular diseases, although its efficacy has not been proven.

Thanks to Jan Linders for suggesting this molecule.

Polydatin structure

Poly-dating?


Mallard Blue

This is a dye that's recently been developed to bind to the blood factor, heparin, very quickly. Because of its blue colour, and the fact it works so quickly, the chemists at the University of York who developed the dye named it Mallard Blue, after the fastest steam train in the world, The Mallard, which is in the National Railway Museum in York, and is this same shade of blue.

Thanks to Jan Linders for suggesting this molecule. The image below is from their paper.

Thanks to Jan Linders for suggesting this molecule. Ref: S.M. Bromfield et al., JACS (2013); dx.doi.org/10.1021/ja311734d

Mallard Blue



Fat dog

Rotundic Acid

This acid isn't a weightwatcher's nightmare - or even a particularly round-shaped molecule. It gets its name from being isolated from the holly bush (Ilex Rotunda), and is being suggested as a possible chemotherapy drug to combat cancer.

Thanks to Jan Linders for suggesting this molecule. Ref: Y-F. He, et al, Bioorg. Med. Chem. Lett. 23 (2013) 2543–2547.

Rotundic acid


Herniarin

Herniarin

A side-splitting molecule, but perhaps not in the funny sense? It actually has nothing to do with medical hernias, but gets its name from the plant from which it's extracted, the superbly named 'smooth rupturewort' (Herniaria glabra). This molecule can be considered to be the methoxy analog of thr equally wonderfully named molecule, umbelliferone.

Thanks to Jan Linders for suggesting this molecule. Ref: F.S. Santamour L.G.H. and Riedel, Biochem. System. and Ecol. 22 (1994) 197–201.



Antipathine

Is this the molecule that all the other molecules dislike? It's actually an alkaloid that's derived from the South China Sea black coral Antipathes dichotoma.

Thanks to Jan Linders for suggesting this molecule. Ref: "A. Berndt et al., Synlet. 24 (2013) A–E.

Antipathine


Texaphyrin

Texaphyrin

A texaphyrin is an enlarged version of the porphyrin rings that form the basis of chlorophyll and hemoglobin. Normally these have 4 amine groups bonded to a central metal, but because this new molecule was synthesised in Austin, Texas, and everything is bigger in Texas, this one's got 5 amine groups, and a larger ring. The resulting molecule has a flat 5-pointed star, which closely resembles the 'lone star' on the flag of Texas, and that's how the molecule got its name. It was going to be adopted as the official 'molecule of Texas', but got beaten by buckyballs.

Thanks to Andrew Dalebrook for suggesting this molecule. Ref: C. Preihs et al., Inorg. Chem. (2013) dx.doi.org/10/1021/ic400226g.

Texas flag


Frustration

Frustrated Lewis Pairs

As you may know, a Lewis acid is a molecule that bonds to another by accepting a pair of donated electrons, whilst a Lewis base is a molecule that donates a pair of electrons to form a bond. If there are large, bulky sidegroups near the donating atom, the donation and/or acceptance of the electrons can be prevented or hindered, and in this case we get what's called 'frustrated' Lewis acids and bases'. Some molecules contain 2 groups, one an acceptor and one a donor, which usually link together in a polymerisation reaction. However, if these atoms are both sterically hindered by bulky groups, the reaction cannot occur and so the molecule is said to possess a 'frustrated Lewis pair'. An example of one is shown in the diagram, where the B would like to be the acceptor atom (Lewis acid) and the P the donor atom (Lewis base), but they can't react due to the steric hindrance - and it makes them so, so frustrated!

Thanks to Rob Schmidt for suggesting this molecule. Ref: D.W. Stephan and G. Erker, Angew. Chem. Int. Ed. 49, (2010) 46.

FLP


Schizocommunin

Schizocommunin

This sounds like a place where paranoid hippies go to relax. It gets its name after being extracted from m the liquid culture medium of Schizophyllum commune which was isolated from the mucous plugs obstructing the bronchus of a patient with a lung disease. I bet that's a day etched in the memory of the poor grad student, when their supervisor handed them a bucket of infected lung goo and asked them to extract something useful from this! It might have been worth it, as this molecule shows some anti-cancer properties.

Thanks to Jan Linders for suggesting this molecule. Ref: K. Uehata, et al, J. Nat. Prods (2013).



Pyrimidoblamic acid

This has an unusual name - it doesn't appear to be pyrimidal, and I can't see where the 'blamic' part comes from either. But it's a fragment of Bleomycin A2 (the major component of the clinical anticancer drug Blenoxane). If it were explosive, maybe it'd be renamed pyrimido-kablam-ic acid!

Thanks to Jan Linders for suggesting this molecule. Ref: A.S. Duerfeldt and D.L. Bloger, J.A.C.S. (2013) dx.doi.org/10.1021/ja412298c.

pyrimdoblamic-acid


bilirubin

Bilirubin

Billy Who? This molecule is not named after a person called Billy. In fact it's short for bilis (bile in Latin) and ruber (red), and was named after the yellow/red pigment found in bile. It's also what makes urine yellow, the brown color of feces, the yellow discoloration in jaundice, and the yellow colour of bruises. It is a breakdown product of haem, and is light sensitive. Billy's brother, billiverdin, is the green pigment found in bile and the two pigments can be converted back and forth by reduction and oxidation.



Obewan Kenobe

Kinobeon

A long time ago, in a galaxy far, far away... there was a molecule that sounded like it was named after the Star Wars character Obewan Kenobi. It's actually a biological antioxidant that's derived from safflower.

Thanks to Alexander Wolf for suggesting this molecule. Ref: T. Kanehira, et al, Life Sci. 74 (2003) 87.

Kinobeon A


Putnisite

Putnisite

No, Vladimir Putin hasn't named a mineral after himself (yet). This is a newly discovered purple strontium-calcium-chromium-sulfate-carbonate mineral from Australia, named after the two miners that found it Andrew and Christine Putnis. But its name resembles geologists' nickname for a useless rock, leverite, as in: leave 'er right there. Putnisite could be 'puttin it aside'.

Thanks to Bastiaan Vos for suggesting this mineral. Ref: Huffington Post, May 7th 2014.



Sux

This molecule really Sux, man. In fact it doesn't suck, it's actually quite useful. Sux is the standard abbreviation for Suxamethonium chloride, which is used medically for muscle relaxation and paralysis. Its main use is to relax the throat muscles during intubation (putting a tube down the throat into the lungs), or to relax a patient's muscles during electric-shock therapy. It's also used in combination with sedatives and analgesics to immobilise and euthanise horses. So, I suppose, if you're a horse, this molecule really sux.

Thanks to Tim Harrison for suggesting this molecule. Ref: H.R. Dorkins, Med. Hist. 26 (1982) 145.

SUX


TEA

TEA

This molecule isn't the one found in tea, but is actually an acronym for triethyl aluminium. TEA is one of the components of the Ziegler-Natta catalyst used to make polystyrene, and is quite unusual in that it's a dimer where the bridging carbons nominally have 5 bonds. Another molecule with the same acronym is triethylamine, which has a fishy ammonia-like smell. Yet another molecule with the acronym TEA is triethanolamine, which is an emulsifier and surfactant often found in detergents, cleaning fluids and shaving foam.

Thanks to Tim Harrison for suggesting this molecule.

teacup


Duvel

Duvelisib

This molecule should be a favourite in Belgium, where the beer Duvel is brewed. It sounds like someone asked Yoda which is his favourite beer: "It is Duvel, I sip". It's actually a newly discovered drug which may help with immune diseases.

Thanks to Jan Linders for suggesting this molecule.

Duvelisib


Pending...

There are some molecules that I've heard of but don't have information about or I don't know the structure. I'm not even sure if some are genuine molecules. If you can help with any of these, please let me know. They are: Cyrillic Acid, Sarcastic acid, Barbaric acid, Sardonic acid (do any of these 3 exist?).