moleculeline

More Molecules with
Silly or Unusual Names

moleculeline

Rudolphomycin and Rednose

Rudolphomycin is a antitumor antibiotic compound. It was named following a series of such molecules derived from 'bohemic acid' - which was given its name because the discoverer Dr Nettleton of the Bristol-Myers Compnay was an avid opera fan and called it after the Puccini opera La Bohème. Derivatives of this were then given names from characters in the opera, such as mussettamycin and marcellomycin, after Musetta and Marcello, and rudolphomycin after the character Rudolph. Other molecules named in a similar fashion include: alcindoromycin, bohemamine, collinemycin, mimimycin, and schaunardimycin. According to his daughter Mignon, the joke in their family was that their father started naming his chemical compounds after opera characters because he ran out of daughters, all four of which had been named after female opera characters. (Mignon was named from the opera Mignon by Ambroise Thomas).

On degradation of rudolphomycin, a new sugar was obtained, which was christened 'rednose'. This rather silly name was probably allowed to stand since the paper was submitted on December 21st 1978, and the Journal editor probably had the Yuletide spirit! Again, according to Mignon, her father actually got reprimanded at the company for not taking his job seriously enough. Unlike the Journal editor, the company bosses were not filled with the Christmas spirit, and it was probably long past December when they found out about it. However, since the name had been accepted already, there was nothing they could do about it.

The same group also named a new antibiotic Rebeccamycin, which is also apparently from an opera popular at the time (probably Rebecca by Wilfred Josephs, based on the book by Daphne du Maurier).

Thanks to Janet McBride for suggesting these Christmas-ey molecules, to Jan Linders for rebeccamycin, and to Mignon Schriek (nee Nettleton) for the insight into her father's naming of these compounds. More info: J. Am. Chem. Soc. 101 (1979) 7041, and J. Antibiotics 15 (1987) 668.



George and Bi-George

The story goes that when undergraduate James Carnahan achieved the synthesis of a new cage structure at Columbia University, he asked his supervisor Prof Katz to suggest a name for it. Since trivial names are often arbitrary, he suggested 'George'. When George was heated with a Rh catalyst, it dimerised to produce Bi-George!

Eurekamic Acid

Eureka! was supposedly the exclamation used by Archimedes when he found something interesting in his bath water. It means 'I have found it', and so when researchers at May and Baker discovered this acid, they felt it was such a 'Eureka moment' that they named the molecule after it.

Catherine

I don't know much about this molecule except that its name comes from the plant Catharanthus roseus. I'm surprised, though, that it's not wheel shaped...

Complicatic Acid

This molecule didn't get its name because it was complicated to make, rather from the plant Stereum complicatum from which it was isolated.

Ptelefolone

This molecule rings a bell...It gets its name from the hop tree Ptelea trifoliata, but I don't know much else about it.

Pterodactyladiene

This is a group of molecules that resemble the ancient flying reptiles. The R groups can be altered to give different sized 'heads' or 'tails'.

Thanks to Ewart Shaw for suggesting this molecule.


Miazole and Urazole

If you pronounce the 'a' as in 'cat', and the 'z' as an 's', then you get the classic chemistry joke: What's the difference between miazole and urazole? The size of the ring...
And shouldn't there be a 'herazole', a 'theirazole' and an 'ourazole' to get a complete bunch of azoles? Actually, the proper name for miazole is imidazol, but that spoils the joke a bit.... There is even a largazole, but not yet a huge-azole or complete-azole.

Thanks to Steve Stinson for suggesting the azoles, and to Jan Linders for the reference to largazoles: K.E. Cole et al, JACS 133 (2011) 12473.

Largazole

Stylissazoles and Hymenialdisine

Another bunch of azoles have recently been extracted from the Pacific sea sponge (Stylissa carteri) and have been called stylissazoles... I'm sure I've met a few of those in my time...

A structurally related molecule is called hymenialdisine (shown on the right)...I wonder if this is a constituent of extra-virgin olive oil...?

Thanks to Jan Linders for the refs to styllisazoles: K. Patel et al., Angew. Chem. Int. Ed. 49 (2010) 4775. Thanks also to Thomas Bannister for correcting its structure, and also for suggesting hymenialdisine.

hymenialdisine

Ethyl Lactate

This is another standard undergraduate chemistry joke, based around the fact that Ethyl sounds like a common female name. "How do you make Ethyl lactate...?" Other names involving "Ethyl" such as Ethyl palpitate, Ethyl fornicate and the spinster Ethyl celibate also make good jokes, but unfortunately the corresponding acids (palpitic, fornic and celibatic) are unknown. In a similar vein, is copper tartrate what's paid to policewomen who are impersonating prostitutes?

Thanks to John Figueras for suggesting this molecule and to Suds Mixer for info about it, and Colin Metcalf and to Peter Rice for the ethyl celibate and tartrate jokes, respectively.

Cristane

So what's so amusing about cristane? Well, for the non-biologists amongst you, a 'crissum' is the name given to the anus of a bird! Tricyclo[5.3.0.0]decane, was nicknamed cristane since on the evening it was first discovered in Brown University, someone left the window open. A pigeon got into the lab overnight and did what pigeons do - all over the lab and equipment. The clean-up crew named the new molecule in honour of the part of the bird's anatomy that had provided the 'surprisingly abundant gift'.

Birdcage

This molecule is so called because it, um, resembles a birdcage, duh. Maybe it should have been used to capture the aberrant pigeon from cristane, above...


Apolloane and Rocketene

Apolloane was created at the same time as the Apollo 11 moon landings. When drawn as a flat diagram the structure bears a striking similarity to a rocket, with side fins and exhaust. And the OH is even located at carbon 11, to get apolloane-11-ol. Apparently, Neil Armstrong's personal memorabilia include a reprint of the chemistry publication which named it: [A. Nickon, et al., J. Am. Chem. Soc. 92 (1970) 1688.]
On a similar theme, Rocketene was also named for its structural resemblance to a rocket.

Thanks to Jarrod Ward for suggesting this molecule.

Manxane and Manxine

Manxane resembles the coat of arms of the Isle of Man (called a triskelion) which consists of 3 armoured legs in a circle. Bicyclo[3.3.3]undecane was named Manxane since it closely resembles this Manx emblem. Later on, a group of researchers at the University of Illinois created an analog of Maxane with a bridgehead nitrogen, and so called it Manxine. Professor Leonard, who created this molecule, thought Manxine sounded like a girl's name - so we now have the male (manxane) and female (manxine) versions of the molecule, with the difference being what is situated between their legs!

Cornerstone

Ok, this is a bit of a cheat, since its real name is b-corrnorsterone, but it's known as 'cornerstone' by all those that work with it. It got its name since it's a ketone with a norsteroid structure (hence 'norsterone') and the discoverer, Robert Woodward at Harvard, thought it might eventually be possible to transform it into a corrinoid.

Adamsite

This molecule was named after the renowned chemist Roger Adams of the University of Illinois. It's actually a chemical warfare agent, and is 'a damn sight' better at killing people than most other molecules...

BON-BONs

These ring structures are not what makes French sweets taste sweet. Heterocyclic dimers like the one shown in the picture (where you vary the R, R' and R" groups) are named from the fact that the ring atoms in sequence spell out BON-BON.

Performic Acid

An actor's favourite chemical? As you might expect from a per-acid, it's a very strong oxidising agent, and always puts on a great per-formance!

Thanks to Andy Dicks of the University of Toronto, for suggesting this molecule.

R-CMP

As anyone from Canada will know, RCMP are the initials for the Royal Canadian Mounted Police, but this molecule isn't their emblem. R-CMP is actually short for R-cytidine monophosphate, and is actually a component of RNA, the nucleic acid which transcribes the genetic information from the DNA so that it can be translated into protein.

Thanks to Amanda Musgrove from the University of Alberta, Canada (of course) for suggesting this molecule.

Sonic Hedgehog

Fruitfly genetics has a rich history of 'creative' nomenclature, often based on the appearance of flies that have the gene in a mutated form. One of these mutated genes made fruitfly embryos look like hedgehogs, since their spines grew all over their body rather than just in specific places - so it was name the 'hedgehog' gene. The vertebrate analogue was called 'Sonic' Hedgehog in order to distinguish it from its insect-forming version, and was given the abbreviation Shh. Geneticists studying other organisms are happy to elaborate on this when they can get away with it, and there are other variety of hedgehog genes called Indian hedgehog (Ihh), Desert hedgehog (Dhh), and even 'Tiggy-Winkle hedgehog' (TWhh)! There are also genes called Sleeping Beauty, Tubby, and most recently the puberty gene, "Harry Potter".
In early 2009, US scientists at discovered a potential inhibitor of the Hedgehog signalling pathway. One of the co-authors of the paper in Nature Chem. Biol., Lee Peng, of Harvard Medical School, said the team had a little fun with the naming rights to the new molecule. "As Sonic hedgehog was deliberately named after the Sega videogame character Sonic the hedgehog, we wished to adhere to the convention established by the original investigators in naming our inhibitor of Sonic hedgehog signalling," he said. "Dr Robotnik is Sonic's archenemy, so we decided that 'robotnikin' was an appropriate name for our compound." To me, robot-nikin' sounds like the occupation of a thief who steals androids.

Thanks to Greg Valure for suggesting this gene, and to Richard Williams from the Institute of Cancer Research and Geraldine VdA for providing some of the info about it, to David Bradley for the other gene names, and to Jan Linders for the robotnikin details. More details on Sonic. Ref: B.Z Stanton et al, Nature Chem. Biol. 5, (2009) 154. More fruitfly gene names and their stories can be obtained from www.flynome.com, and thanks to Jeremy Bracegirdle for supplying this link.

Gibberelic Acid

Gibberelic acid isn't a psychotropic drug that makes you gibber insanely like a monkey...it's actually one of a number of gibberelins, which are plant hormones which control various aspects of plant growth.

Thanks to Mathias Disney for suggesting this molecule.

Darlingine

This molecule is lovingly extracted from the Brown Silky Oak tree, Darlingia darlingiana.. It hasn't been analyzed biologically yet, but may have activities similar to other tropane alkaloids, such as muscle contraction and stimulation...(But it only works if you treat it nicely...)

Thanks to Christopher Wells for info on this molecule.

Jesterone

This playful and mischievous molecule is found in a fungus, Pestalotiopsis jesteri, which lives inside yew trees.

Thanks to Christopher Wells for info on this molecule.

Trunkamide

Trunkamide has nothing to do with elephants, although its spacefill structure shown right looks a bit like an elephant. It was isolated from a sea squirt living in the Great Barrier Reef, and is reported to have anti-tumor properties.

Thanks to Christopher Wells for info on this molecule.

Diurea

As you might expect, this molecule and its derivatives are often used as a fertiliser, being splattered liberally around fields of crops. It's also known as biurea, but its proper chemical name is N,N'-dicarbamoylhydrazine. It's also sometimes used as flow improver in paints and greases. So next time you paint your house you can tell people you're covering it with diurea...

Thanks to Gene Morselander for info on this molecule.


If it's Paris-ite, there should be an Eiffel Tower.

Parisite

This mineral sounds like it grows on other minerals. It is found in Columbia, and it's named after J. J. Paris, who was a mine proprietor at Muzo, north of Bogota, Columbia. It is a member of the Bastnasite group of complex carbonate-fluoride minerals, and has the formula Ca(Nd,Ce,La)2(CO3)3F2.

Thanks to Tanuki the Raccoon-dog for info on this mineral.

Clintonite

This mineral sounds like it should be found in close proximity to 'internite' or 'lewinskyite'..., but it was actually named after American Statesman De Witt Clinton (1769-1828), not the notorious ex-President. Its formula is Ca(Mg,Al)3(Al3Si)O10(OH)2 (a calcium magnesium aluminosilicate hydroxide mineral), and it's related to margarite. It is found abundantly in the northern extent of New York.

Thanks to Friedrich.Menges and Steven A. Hardinger for info on this mineral, and to Hans Hillewaert for the link to the image.

Sodamide

This is the shorthand name given to the common chemical, sodium amide, NaNH2. It sounds like it belongs in close proximity to other molecules in this list, such as arsole, anol, skatole, and maybe fruticolone...But I'm not letting it get anywhere near miazole!

Thanks to Germanicus Hansa-Wilkinson for suggesting this molecule.

dUMP

Maybe dUMP is the molecule into which all the waste atoms are thrown? In fact dUMP is the acronym for 2'-deoxyuridine-5'-monophosphate, and is an RNA transcription subunit - or a bit of the thing that makes proteins, and is one of the building blocks of DNA. Maybe dUMP makes so-called junk-DNA? dUMP is a deoxygenated form of RUMP, which is another of the bases found in (near the bottom of?) RNA. If you want to have a 3D dump, click on the structure to the left.

Thanks to Christopher Putnam of the Ludwig Institute For Cancer Research, La Jolla, CA, and Peter Traill from the University of Dundee, and John Gosden for info on this molecule.

BARF

There are two molecules that are called by their shorthand name of BARF. The first, often written as BArF, is a halide abstracting reagent B[3,5-(CF3)2C6H3]4-, i.e. two CF3 groups on each phenyl, and four of those phenyls on a boron. The second is written BARF, and is the shorthand for tripentafluorophenylborane (B-Ar-F), see structure on the right. It is mainly used as a strong Lewis acid to abstract a methyl group in the reaction to make a highly active ethylene polymerization catalyst. So you really can barf into a plastic bag...

Thanks to Ken Weakley for suggesting the second BARF, and to Thomas Vaid at Washington University for the first BArF.

Small-breasted-dog

Yes, it really is called that, but in Spanish! The molecule is actually named 'Perrottetin-a' which (almost) literally means "small-breasted-dog" (Perro=dog, tetita=small breast). The molecule gets its name from the liverwort plant from whence it is extracted, Hepatica Radula perrottetii, which itself was named after the botanist George Samuel Perrottet (1793-1870). There is another related compound, perrottetinene, which is structurally similar to THC, the active ingredient in cannabis. Maybe this molecule should be called 'stoned small-breasted dog'!

Thanks to Enrique Pandolfi and Kay Dekker for providing the info on this molecule. See: Y. Asakawa, K. Takikawa, M. Toyota, T. Takemoto, Phytochem., 21, (1982) 2481.

Centaureidin

Centaurs are creatures which are half horse, half human. The molecule centaureidin got its name because it was extracted from a flower called Centaurea corcubionensis, which is related to the cornflower. It was discovered along with a molecule named centaurein, found in the same plant.

Thanks to Victoria Barclay from ACD in Toronto and to ShadowFox for providing the info on this molecule. Here is a scientific article about Centaureidin.

Sandwicensin

John Montagu, The Fourth Earl of Sandwich, was a notorious gambler who would often go from pub to pub in London on gambling marathons. To satisfy his hunger while continuing to gamble, he would order slices of meat between two pieces of bread. Thus, was the sandwich born. But how about "Sandwicensin"? As a newly identified cytotoxin, isolated from a soggy old sponge at that, we guess that it must be somewhat less than appetizing!

Thanks to Victoria Barclay from ACD in Toronto for providing the info on this molecule.

Magic Acid

'Magic Acid' is the name given to one of the strongest of the inorganic 'superacids'. It is made by mixing together antimony pentafluoride (SbF5) and fluorosulphonic acid (HSO3F), and it is so strong (pKa = -20) that it is capable of protonating even saturated alkanes, like methane, to produce carbonium ions.
On a similar theme, Aldrich used to sell methyl fluorosulfate, which they labelled "Magic Methyl" because it methylates nearly every functional group. However magic methyl was withdrawn due to it being dangerously reactive... but you can still buy the slightly less hostile molecule methyl trifluorosulfate.
Also, Magic Factor-1 (derived from the acronym for Met-Activating Genetically Improved Chimeric Factor-1) is an engineered protein that helps keep certain cells alive and which may be used to treat muscular dystrophy. It's been shown to improve the running speed of mice which have previously had wasted leg muscles...magic indeed!

Thanks to Indranil Sen from the Utah State University for suggesting magic acid, Roger Alder for magic methyl, and to Rob Towart for Magic F-1 (See: M. Cassano, et al, PLoS ONE 3, (2008) e3223).





Profilactin

Actin is an intracellular fiber protein (best known in muscle contraction), and profilin is a protein that interacts with actin to "promote filament" formation. When profilin and actin are bound together, the complex was originally labelled: "Profilactin", which is most appropriate since it was first isolated in sea urchin sperm. However, I'm told this name was not officially recognised. Also, the first submission of a name for this protein was "screw-in"...because when the filament is ejected from the tip of the sperm, the globular actin shoots outward in a screwlike motion. Although this, too, was a clever name given the protein's location...it was turned down as well. Its official name is now 'the profilin-actin complex'.

Thanks to Blair Boehmer from Duke University, Shefa Gordon at Berkeley and to Leigh Arino de la Rubia for info on this molecule.


Profilin bound to an actin monomer. The profilin protein molecule is shown in blue and the actin in red. ATP is shown in green. [Modified from the original image in 'Molecular Biology of the Cell' by Alberts, et al.]

Crocidolite

This has nothing to do with crocodiles, but is actually the name of the mineral form of blue asbestos, with formula Na2Fe5Si8O22(OH)2. It either got its name from the Greek word for 'woolly', or it was named from the geographic location of where it was first discovered. viz. the Crocodile River Valley in South Africa. This is just outside Nelspruit in Mpumalanga South Africa (look on the Eastern part of a SA map - next to the Kruger National Game Park).

Thanks to Indranil Sen for suggesting this molecule and to Stuart Kidd and Grant Little for providing some of the information about it.



Bellendine

For non-English readers, I won't tell you what 'bell-end' is slang for, but a clue might be that the molecule is extracted from the flower Bellenda Montana, which should have a purple head...

Piano Stool

These are a group of molecules made from a transition metal bonded to a cyclopentadienyl ligand, so that they resemble a 3-legged piano stool. I don't know if molecules have been made with other numbers of 'legs', such as milking stools, etc. But would a sample of this molecule be called a 'stool sample'?

Thanks to Sean Pearce for suggesting this molecule, and to Dennis Gorden for the joke.



Megatomic Acid

This molecule has nothing to do with nuclear explosions, and neither is it the magic formula that creates a superhero. But it is in fact named after the black carpet beetle Attagenus megatoma (Fabricius), in which it is the principle component of the beetle's sex attractant. Its proper name is (3E,5Z)-3,5-tetradecadienoic acid.

Thanks to Simon Cotton for suggesting this molecule, and for more info see: New J.Chem. 25 (2001) 223.

Grass-Hopper Ketone

I'm guessing that this molecule gets its name as a result of laziness. It's extracted from the defensive secretions of the flightless grasshopper Romalea microptera, and I assume that after spending hours in the field, annoying the grasshoppers, and then catching them and 'milking them', the scientists involved were too tired to think of a proper IUPAC name, so they came up with the inspired name, grasshopper ketone.

Thanks to Polyploid2 for suggesting this molecule, and for more info see: J. Meinwald and L. Hendry, Tetrahedron Lett., 1657 (1969)



Shattuckite

This mineral sounds painful, but is actually just named after the locality in which it is found, the Shattuck mine in Arizona. Its actual formula is Cu5Si4O12(OH)2.

Thanks to Martin Harris for suggesting this mineral.

G(olf) proteins

These are a class of proteins called G-type proteins, some of which are linked to the olfactory system - hence the name G(olf) proteins. They help trigger the biochemical synthesis of neurotransmitters, which eventually leads to signalling, and gives us a sense of smell.

Thanks to Boaz Laadan for suggesting this mineral. More info at: http://www.leffingwell.com/olfact3.htm



Germylene

The GeH2 radical is called germylene, which is similar to an antiseptic ointment found in the UK called Germolene. I doubt that germolene contains germylene, though, as GeH2 is very toxic...

Thanks to Victor Sussman for suggesting this molecule.

Khanneshite

It's amazing how this name got past the International Mineralogical Association when they approved the new mineral name. It was named after the discovery locality at Khanneshin, Afghanistan. All minerals have the suffix '-ite'. and so the name they gave to this mineral is - Khanneshite. I can only presume that there were no Scots on the committee that approved the name... I can't find any photos or structural images of khanneshite, so the image on the right is actually of the burbankite structure which, according to the literature is identical to that of khanneshite.

Thanks to Brian Jackson from the National Museums of Scotland for suggesting this mineral.



BCNU

Bis(Chloroethyl) NitrosoUrea has got quite an appropriate acronym, BCNU (be seein' you...), since in early medical studies it was found to be so toxic, it killed the patient! It is actually highly carcinogenic, causing tumors in rats, mice, rabbits, and probably humans as well. Ironically, it is actually used as a treatment for brain cancer and other diseases such as Hodgkin's lymphoma.

Thanks to Terence Bartlett for suggesting this molecule.

SEX

SEX is the official abbreviation of sodium ethyl xanthate, which is a floatation agent used in the mining industry. Apparently you can get SEX in both solid and liquid forms (should that be hard and wet SEX?), and according to Australia's National Industrial Chemicals Notification and Assessment Scheme signs of high exposure to SEX include 'dizziness, tremors, difficulty breathing, blurred vision, headaches, vomiting and death'. Sound familiar...?
On a related note, there's another flotation reagent, KAX, potassium amyl xanthate, which has the same function, and the same smell!

There's another molecule that sometimes called 'sex'. A byproduct impurity in the explosive RDX, 1-acetyl-3,5,7-trinitro-1,3,5,7-tetrazacyclooctane, has been dubbed SEX by some researchers. I haven't yet found out why this acronym was used, other than to be silly and maybe to keep people awake during long, boring conference talks. But, again, it leads to some great descriptions in papers. After synthesis, the impure material can be called 'dirty sex' or even 'crude sex', and when extracted it can produce 'analytically pure sex'.

Thanks to Joseph Wiman and for suggesting this molecule and Nicholas J. Welham for some of the info about KAX. Thanks also to Rob Schmidt for info about the RDX version of sex.


Austin

Austin has nothing to do with Austin cars, Austin Texas, or even Austin Powers...it's actually a mycotoxin, which comes from the fungus Aspergillus ustus, which might have given it it's name but I'm not sure.

Thanks to Chris Fellows for suggesting this molecule and to Mark Johnston for suggesting how it got its name.



Pantolactone

This molecule sounds like it belongs in underwear, or on stage in a pantomime. As you might expect, it is used as a reagent in the synthesis of CAMP ligands (cis-2-(aminomethyl)-1-carboxycyclopropane)...

Thanks to Gary Randall for suggesting this molecule.

Technetium Cow

'Cow' terminology comes from the nuclear industry, and it has nothing to do with the unfortunate cattle that live near nuclear power plants. A radionuclide, such as 99Mo (as its ammonium salt), is stored in a column, called a 'cow'. Its decay product, technetium-99m, is continually produced, and it can be flushed out of the "cow column" in a process called 'milking the cow'. The 'technetium cow' isotope is then used in bone scans, and has a 6 hour half-life. And I'm told that there used to be an 'Americium Cow' in Harwell in the 1950s. On a related theme, molybdic acid anhydride (MoO3) is often referred to as 'Moo'.

Thanks to 'Plutonium' Page Sebring for providing the info about this element, Ian Ferguson for the Am Cow info, and to Jonathan Montgomery for info on Moo.


Erectone

No, this isn't one of the ingredients in Viagra...but is actually one of a group of compounds extracted from the Japanese/Chinese herb Hypericum erectum, which is often used in traditional Chinese medicine to treat arthritis, rheumatism, and as an astringent.

Thanks to Christopher C. Wells for providing the info about this molecule.

Abiguene

Ambiguenes are cytotoxic and fungicidal indole alkaloids that are extracted from blue-green algae. As many as 7 are known. Although it could just be 5. Or 10. Or maybe they are a different type of molecule altogether...? It is very appropriate that in 1980 Pelletier et al. had to revise the original structure, since it was wrong the first time around.

Thanks to Christopher C. Wells for providing the info about this molecule. See: S.W. Pelletier et al, J. Am. Chem. Soc. 103 (1981) 6536.

Lovenone

This is a cytotoxic agent isolated from the skin of a nudibranch (of course) Adalaria loveni which lives in the North Sea.

Thanks to Christopher C. Wells for providing the info about this molecule.

Boldine

This is an aporphine alkaloid extracted from the plant Peumus boldus. It is a good antioxidant and can protect the liver, although there are rumours it makes your hair fall out...

Thanks to Christopher C. Wells for providing the info about this molecule.

Inflatene

This is a hydrocarbon compound that is isolated from soft coral (Clavularia inflata) and is apparently toxic to fish - maybe it makes them all look like puffer fish ;-).

Thanks to Christopher C. Wells for providing the info about this molecule.

Bowtiediene

This is another molecule named after its shape - although the preferred name is spiropentadiene.

Thanks to Isaiah Shavitt for providing the info about this molecule.

Prodigiozan

This molecule has a name that sounds like the Biblical 'prodigal son', who finally returned home. The structure shown is actually the related molecule, prodigiosin, since I can't find the structure of Prodigozan...well, not until it finally comes back here. :-) Both molecules are antibiotic pigments produced by Chromobacterium prodigiosum, with antimicrobial and cytotoxic properties. There are also a whole range of related molecules called prodiginines, presumably extracted from the same bacteria.

Thanks to Susanne Wikman from Vaxjo University, Sweden, for providing the info about this molecule, and to Jan Linders for prodiginines.

Arachidonic Acid

This molecule sounds like it has something to do with spiders, but it's actually made in the human body. It is synthesised from linoleic acid and plays an important stage in the inflammatory process of the human body - some Non-Steroidal Anti-Inflammatory Drugs (NSAID's) are believed to work by inhibiting this stage. But nobody has managed yet to artificially produce medical grade arachadonic acid (it's mainly used in infants) so the only source is rats urine - it needs a day's worth of urine from 10,000 rats to produce a single dose! Now, that really is taking the p***!

Thanks to Mark Croker for providing the info about this molecule, and to Howard Wilk for correcting the structure.




Warfarin

This molecule sounds like it could be a warfare agent, and it is...if you're a rat. It's a rat poison which stops the blood clotting, so the rats bleed to death. It also has medical uses in blood thinning and clot prevention. Apparently it gets its name since WARFarin was the first patentable product of the Wisconsin Alumni Research Foundation (WARF). An interesting story about warfarin is that it may have been used to kill Stalin.

Thanks to Charles Turner and Michael Bailey and Larry Baum for providing the info about this molecule.

(R)-DICHED

This is the abbreviation for (R,R)-1,2-dicyclohexyl-1,2-ethanediol. The authors of the paper which describes it (Organometallics, 2001, 20, 2920) state "a number of DICHED boronic esters were screened by NMR...". I wonder who the real DIC-HED is?

Thanks to Alex Yuen of the University of Sydney for providing the info about this molecule.

Lunatoic Acid

Lunatoic acid is an azaphilone isolated from Cochliobolus lunatus. It is a good antibiotic and also causes sporation in fungi. Perhaps it kills bacteria by causing them to die by insanity, in the same way canine distemper kills animals.

Thanks to Christopher Wells of the University of Sydney for providing the info about this molecule.

Microlite

Microlite is not one of the components of a small airplane, but is a tantalum/niobium oxide mineral that can be slightly radioactive. Its correct formula is: (Ca, Na)2Ta2O6(O, OH, F).

Thanks to Neil Brew for suggesting this mineral. More info can be found here.

beta-BuTX

This molecule sounds like the sales pitch for an exercise regime (get better buttocks using this!), but it's actually a snake venom with full name beta-Bungarotoxin). maybe the venom is more potent if the snake bites you on the Butx. :-)

Thanks to Satan's Little Helper and Joerg Fruechtel for info on this molecule.

DAMN

DAMN is the acronym for diaminomaleonitrile, which is a particularly nasty molecule containing lots of cyanide groups.

Thanks to Michael Stewart for suggesting this molecule.

"Frankly my dear, I couldn't give a Diaminomaleonitrile..."

Allene

Allene is quite a sad molecule in Holland, since in Dutch it is called 'alleen', which simply means 'alone'. And if you add a benzene-ring you'll get Benzo-allene which means "I'm so lonely" in Dutch. Ahhhh....

Thanks to Karel Vervaeke and Harmen Lelivelt for info on this molecule.

Proton Sponge

This molecule is 1,8-bis(dimethylamino)naphtalene, and according to the Aldrich Chemical Catalog, it is a very strong base with weak nucleophilic character due to steric effects. Therefore it goes by the nickname 'proton sponge', since it mops up all available protons. Similar compounds (e.g. 1,6-diazabicyclo[4.4.4]tetradecane) exist, where you can get a proton inside, but you can never take it out again without destroying the compound. This might be named a 'proton coffin'?

Thanks to Fernando Perna and Roger Alder for info on this molecule.

Mirasorvone

This molecule is part of the defensive chemistry of Thermonectus marmoratus, a beetle recently named the "sunburst diving beetle". The discoverers' at Cornell University named it in honour of the actress Mira Sorvino (right), who, as Dr Susan Tyler in the motion picture Mimic, successfully confronted the ultimate insect challenge.

Thanks to Andy Cal for info on this molecule, and more info is available at: http://www.pnas.org/cgi/content/full/95/6/2733.

Stichtite

Stichtite is a lilac coloured mineral which is a hydrated magnesium chromium carbonate hydroxide. This is fairly common as streaks and small lenses in the green Serpentine in the metamorphic rocks of Western Tasmania, but is very rare elsewhere. It was named after Robert Sticht, a director of a mining company.

Thanks to Martin Harris for info on this mineral.

Cumene

Luckily, this molecule is actually pronounde 'coo-mene', so as to avoid sticky problems when ordering it. It's a fairly standard organic solvent, with a distinctive odour, that is used to make resins, polycarbonate, synthetic fibers such as nylon, and other plastics. Although pronounced the same, it has nothing to do with the Indian curry spice, cumin.

Thanks to J.J. Keating for info on this molecule.


Flea

This is the commonly used name for the amphetamine, N-hydroxy-N-methyl-3,4-methylenedioxymethamphetamine (the N-hydroxylated version of MDMA, Ecstasy). The origin of its name is a bit strange, and is related to the fact that a commonly used code name for the parent compound, MDMA was ADAM. The 6-Methyl homologue was then called MADAM, and, following this pattern, the 6-Fluoroanalogue was to be FLADAM. So, with the N-Hydroxy analogue, the obvious choice was HADAM. But this brought to mind the classic description of Adam's earliest complaint, an infestation of fleas. The poem was short and direct: "Adam had 'em." So, in place of HAD 'EM, the term FLEA jumped into being.

See: http://www.erowid.org/library/books_online/pihkal/pihkal081.shtml for a full description of this naming process. Thanks to J.J. Keating for info on this molecule.

Wheelbarrow Molecule

Here's a molecule that has been designed to look like a wheelbarrow. It doesn't seem to have a full name yet, so it's just called Wheelbarrow Molecule. What's next, a molecular lawn mower? Pruning shears?

Thanks to Plutonium Page for info on this molecule, and the full paper can be seen at: Tet. Lett. 44 (2003) 6261.

Syringic Acid

This molecule is named after the lilac plant, since the Latin name of lilac genus is Syringa. Lilac bushes possess hollow sticks which were used in ancient times to make flutes. In fact, there is a kind of flute that is called "siringa" in Spanish. In Latin the meaning of the word siringa was extended to include hollow tubes made of any material, including metal. Later, when hollow needles began to be used to inject liquids in the body, quite naturally they were called syringes. Funnily enough, syringic acid can be found in blueberry plants, which, in Latin, are called Vaccinium. Quite a coincidence! On a related theme, there is also a Vaccenic acid (Z-11-octadecenoic acid, also known as asclepic acid) although its structure is not related to that of Syringic Acid.

Thanks to Andrei V. Rogoza, Kastytis Beitas, Gabriel Tojo and to ShadowFox for info on this molecule, and to Tue Bruun Petersen for the info about vaccenic acid./p>

Tortuosine

This molecule is an alkaloid extracted from the plant Amaryllidaceae, but I bet it was extracted very sloooowwwllly. In fact, this naturally occurring organic compound and the following one (assoanine) had plant-derived names that were so compelling that Lee Flippin designed and executed total syntheses of them just for the fun of it.

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 65 (2000) 3227.

Assoanine

This molecule gets its superb asinine name from the plant from which it is extracted, the gloriously named Narcissus assoanus!

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 59 (1994) 3497.

Bicyclohexyl

This molecule not only has a name that sounds like a bicycle, ironically it even looks like one too. In fact, the bicyclohexyl compound with isopropyl and methyl sidechains (2-isopropyl-3'-methylbicyclohexyl, shown in the diagram) looks even more like a bicycle. There is also tricyclene, but unfortunately its structure looks nothing like a tricycle. Replacing the two cyclohexyl rings with two cyclobutadienyl rings would produce square tyres so the bike could ride on a road paved with repeated cycloidal-shaped bricks. Any doubts about this mathematical oddity should be directed to the French mathematician Jacques Tits (Yes, that's his real name! He mainly worked on group theory, and is famous for the so-called Tits buildings, Tits alternative and Tits group). Of course, this bike could only be used when it's very cold because of the instability of the four-membered rings.

Thanks to Joris van den Heuvel for suggesting this molecule and to Geoff Hallas for correcting the structure, and to Dennis Gorden for the cyclobutadienyl ring version and info on Tits.

NanoPutian Molecules

And today's award for the 'How did they possibly get a grant to do that?' paper, goes to the J. Org. Chem. article by Chanteau and Tour from Rice University in Texas. It concerns making anthropomorphic molecules - i.e. molecules that look like humans...but why anyone would want to do this I don't know... They have been named NanoPutians, after the little men from Lilliput in the book 'Gulliver's Travels'. They come in many forms - the basic building block is the NanoKid (shown right), and from this other variants can be made, such as NanoAthlete and NanoBaker.

Thanks to Neil Edwards for suggesting these molecules.



Nanocars and Nanotrikes

These are the perfect vehicles for driving Nanoputians around their nanoworld. They are made from a rigid framework of benzenes and acetylene groups, with either three or four C60 molecules attached at the ends as 'wheels'. I always wanted a compact...

Thanks to Andrew Byro for suggesting these molecules.
See: Y. Shirai et al, Nano Letts. 5(11), (2005) 2330.

Anisole

Anisole sounds like a molecule the devil would be very interested in collecting, or maybe it's James Brown's ('The Godfather of Soul') favourite molecule? Anisole is aromatic in both the chemical and olfactory sense, and is used in perfumery. It is also an insect pheromone. If you have a lisp, please don't confuse anisole with anethole, which is a structurally related natural product which, incidentally, has the flavour of aniseed.

Thanks to Eric van der Horst for suggesting this molecule and to Matthew Piggott for providing more info about it.

Dopamine

Dopamine (pronounced DOPE-a-mean) is a neurotransmitter in the brain. It is connected to pleasurable sensations (feeling doped) and has been shown to be connected to drug abuse and addiction. Maybe that's why Dopey always had that silly grin on his face...

Thanks to Andrew Byro for suggesting this molecule.

BIG CHAP

This wonderfully named molecule has nothing to do with reproductive hormones, but is actually a detergent with proper name N,N-bis(3-D-gluconamidopropyl)cholamide. Apparently the molecule has reduced electrostatic interactions that prevent your BIG CHAP getting stuck in a chromatography column...

Thanks to Stephen FTM Thompson for suggesting this molecule.

ASS

This is the commonly used acronym for argininosuccinate synthetase, which is a chemical found in the brain. So it seems some people really do think with their ASSes...

Thanks to Allart Kok for suggesting this molecule.

Horseradish Peroxidase

This is the version of the peroxidase enzyme that is isolated from the horseradish plant. Like all peroxidases, it converts harmful peroxide molecules (H2O2) into water molecules (H2O). It is also used to label proteins and nucleic acids as an alternative to radio labelling. The molecule to be labelled is attached to the horseradish peroxidase molecule, and the mixture is then exposed to a substrate that changes from clear to coloured when it is oxidized by HRP. When some of the variations of this enzyme are used as a labels for antibodies, they go by names such as anti-mouse, anti-rabbit, and worryingly...anti-human.

Thanks to Andrew Patterson for suggesting this molecule.

Kojik Acid

This sounds like Telly Savalas' favourite molecule. He was the star of the US TV cop show from the 1970s called 'Kojak'. Kojic acid is used as a skin whitener...but does it work especially well on bald heads?

Thanks to Jerry Van Cleeff for suggesting this molecule.

Porkane

I'm pretty certain this is a spoof molecule, since one of the carbons has 5 bonds. These pig-shaped molecules, where the 'tail' can point up or down, are apparently isolated from porcine lard (pig fat). There are various derivatives of this, including norporkanone, epiporkanone and neoporkanone. For more info on the porkanes, see here.

Thanks to Victor Nikolaev for suggesting this molecule.

Spiroagnosterol (Vice Presidential Steroid)

Years ago this molecule was called the "Vice Presidential Steroid" because of the similarity in name to Spiro Agnew. Mr Agnew was, of course, the Vice President of the U.S. from January 1969 until October 1973, when he resigned. (I've never found a proper reference to this molecule in the literature - does anyone have it?)

Thanks to John L. Meisenheimer, Sr for suggesting this molecule.

Nagarse

Nagarse is a broad-specificity protease, also known as Bacillus amyloliquefaciens subtilisin. It seems to be used to break apart proteins and DNA strands for analysis purposes. Its source is a bacterium and a leech (hirudo medicinalis). Nagarse is actually a trade name, named after the Nagarse (sometimes written 'Nagase') Company of Osaka, Japan.

Thanks to Richard Cammack for suggesting this molecule.

Hardwickiic acid

This is a diterpene which got its name since it was first isolated from the Indian tree Hardwickia pinnata. I assume the tree was named after someone called Hardwick. Anyone know?

Thanks to J.J. Keating from University College Cork for suggesting this molecule and to ShadowFox for more info about it. Ref: R. Misra, R.C. Pandey, S. Dev, Tetrahedron 35 (1979) 2301.

Aristolochic acid A

This aristocratic sounding molecule is derived from species of the birthwort plant (aristolochia). Plants containing the compound were used in herbal medicine as anti-inflammatory agents, but they are now banned in the US and Europe as the compound is nephrotoxic (toxic to the kidney).

Thanks to J.J. Keating from University College Cork for suggesting this molecule. Ref: Fundamentals of Pharmacognosy and Phytotherapy by M. Heinrich, J. Barnes, S. Gibbons and E. Williamson (Churchill Livingstone, 2004., pg 165)

CAMP

This is actually short for cyclic adenosine monophosphate (cAMP) and is a signalling molecule which can be found in almost all eukaryotic organisms. For example, it is used as a nutrient sensor in yeast, and is one of the building blocks of DNA. I wonder if it's responsible for the so-called 'gay gene'...

Thanks to Han Lim for suggesting this molecule and to Tom for info about it.

Cucurbituril

This molecule, which is shaped like a Halloween Jack'o'Lantern, is named after the Latin word for pumpkin (Curcubita pepo). It is now finding lots of use in medical drugs or in potential molecular electronic devices due to the fact that other long thin molecules can be threaded through the hole in the centre to make so-called 'rotaxanes'.

Hipposudoric Acid

This is a malodorous blood-red pigment found in hippo sweat. It absorbs ultraviolet light, thus blocking out the sun's rays like a sunscreen. It is also a natural antiseptic. Its red colour is responsible for the myth that hippos sweat blood.
And still on the hippo theme, there's a molecule called Hipposulphate A, which is a poisonous sulfated sesterterpenoid that's found in a sponge, Hippospongia metachromans, living near Okinawa.

Thanks to Charles Turner for suggesting Hipposudoric Acid, and to Christopher Wells for Hipposulphate A.

Old Yellow Enzyme

This is a flavoprotein that reversibly oxidises NADPH to NADP and a reduced acceptor. In fact, yellow enzymes are any of a number of enzymes having a flavin as a prosthetic group. Historically, NADPH dehydrogenase (occurring in plants and yeast) was called the Old Yellow Enzyme to distinguish it from D-amino acid oxidase, known as, of course, the New Yellow Enzyme.

Thanks to John Moody for suggesting this enzyme.

Ladderane

Ladderane is a chain of fused cyclobutane rings that make up the bulk of dense membranes in certain unusual bacteria. They were discovered in anammox bacteria, which anaerobically oxidize ammonia to dinitrogen. The staircaselike structure of cis-fused cyclobutanes has never before been seen in nature. The most abundant lipid in the bacteria is the methyl ester of a C20 fatty acid with five fused rings. Other ladderane lipids contain three fused cyclobutane rings attached to a cyclohexane.

Thanks to Erik Holtzapple for suggesting this molecule.

Snottites

These are gelatinous, dripping microbial draperies ("mucus stalactites") composed of elemental sulphur, iron oxide crusts, gypsum, and densely packed bacteria, and are found in caves. They are formally known as biovermiculations, although snottite is more descriptive. Snottites are produced by sulfurphilic micro-organisms and drip sulfuric acid with a pH of 0.3 to 0.7. Other microbial structures include "blue goo," which are lavender structures attached to the walls of the cave, and "red goo," a complex clay breakdown product containing clusters of bacterial cells and having a pH ranging from 3.9 to 2.5. Other microbial stalactites go by the fancifully names of "phlegm balls," "green slime," "punk rocks," "hairy sausages," "slime balls," and "beads on a string."
On a similar theme we also have: Coprolites, which are fossil feces, Regurgitalites, which are fossil vomit or pellets, and Cololites, fossilised stomach, gut, or colon contents.

Thanks to Charles Turner for suggesting these.

Coalingite

This superbly named mineral takes some licking... It is actually an interstratified hydroxyl carbonate, but whenever anyone says its name, they normally lower their voices for the rest of the discussion, probably because it sounds like a contraction of coitus and lingus. But it was fact a mineral named after being found in the vicinity of the town of Coalinga, California, which was itself named after 'Coaling Station A'.

Thanks to Phillip W Barak of the Virtual Museum of Minerals and Molecules for suggesting this mineral.

Nootkatone

This molecule with a very silly name is used as a food additive to give grapefruit flavours, as well as in the perfume industry to give odours of citrus fruits and orange peel. It got its name from the yellow cedar, or Camaecyparis nootkatensis, which was itlself named after the native North American called the Nootka.

Thanks to Jim Gobert for suggesting nootkatone and to ShadowFox for some info about its name. Click here for more info on the structure of nootkatin.

Bongkrekic acid

Any visitor to an Indonesian market or dinner table will almost certainly come across tempe (below left), though wonder what on earth it really is. Closely resembling a Camembert cheese in colour and texture with a mushroom-like aroma, tempe is in fact one of the world's first soybean foods. It is composed of cooked soybeans that have been fermented through by an edible fungus which, when mature (like a cheese) becomes an attractive and aromatic white cake suitable for a variety of uses in hundreds of local dishes.

       

But deep in the mountain villages in Central Java, there used to be one rare deadly variety of tempe. Very rare nowadays, and never sold openly anymore, this tempe has killed hundreds. So dangerous is this tempe that the government has banned manufacture of it and imposed a prison sentences to anybody caught making or selling it, since this tempe can contain a toxin more deadly than cyanide. This is tempe Bongkrek. Made from coconut residue after the oil has been extracted, and nothing like good safe soybean tempe, this tempe has the problem that it may become contaminated with a deadly bacterium that lives on the fermented coconut, called Pseudomonas. The coconut only grows the bacterium if it is heavily contaminated, and may produce a deadly respiratory toxin called Bongkrekic acid (above right). In 1988 one batch killed 40 people within two days and over a hundred others were hospitalised. The community in this area, well aware of the risks, have nevertheless continued to eat Bongkrek despite a ban by the government, so irresistible is the taste and texture of this dangerous and illicit pleasure.

Thanks to Tim Lyon for suggesting this molecule.

Bullvalene

This is a very unusual molecule, in that it is fluxional...all the carbons are equivalent due to the rapid movement of the double bonds around the structure. It was first predicted to be like this over 20 years ago by Professor 'Bull' Doering, and was only synthesised in the lab many years later, whereupon his controversial predictions about the structure were verified. The origin of the name is unclear. It is thought to be derived either from his nickname, 'Bull', or from his seminars were affectionately(?) known as Doering's 'bull sessions', since it was at one of these that the structure was first written on the board. Other reports, however, suggest that it was given its name by an irreverent and skeptical graduate student that thought such a structure couldn't exist, and so called it 'Bull-valene'.

Thanks to Marc Kaminski of the University of Freiburg for suggesting this molecule, and to John Perkins for info about the name origin. See: J. Chem. Edu. 78 (2001) 924, for more info.

Barrelene

This molecule is closely related to bullvalene, and got its name from its similarity to the shape and structure of a barrel. Peter Lykos emailed me to say how it happened: "When Howie Zimmerman was getting started at Northwestern University I heard he had synthesized a molecule that in effect was three ethylene molecules condensed about two methyl axes. I could not give it the correct organic chemist's systematic name (I am a quantum chemist) but was fascinated by the notion that there might be a delocalization of six π-electrons around the molecule. So when I called him about its spectroscopic properties I referred to it as 'barrelene' following the idea that the lateral delocalization mught be like the staves of a barrel. He apparently liked that name so that became its trivial standard name".

Thanks to Peter Lykos for suggesting this molecule.

SnOT

Tritiated tin hydroxide goes by the wonderful chemical formula of SnOT. David Ball, a chemist in Cleveland Ohio, was working on isotopomers of SnOH, and after tritiating it found he got SnOT. His paper concludes with the wonderful phrase "Since Wang et al did not use tritium substitution, we can state with certainty that there was no SnOT in their samples".

Thanks to David Ball for studying SnOT and suggesting it for this page. See: D.W. Ball, J. Mol. Struc. (Theochem) 626 (2003) 217, for more info. Thanks also to Sky for the use of the photo of him playing a beggar in a re-enactment of the English Civil War for the Sealed Knot Society.

DOPE

Apparently, DOPE is commonly used by membrane chemists and biochemists - which is something I've always suspected... It's actually short for 1,2-Dioleoyl-sn-Glycero-3-Phosphoethanolamine, and it's a phospholipid used for research into membrane structures. A variant on this is called DOGS, so if you take DOPE, you may go to the DOGS...

Thanks to Sophie Weiss of Leeds University for suggesting this molecule. More info from www.avantilipids.com

Flufenamic Acid

This molecule with a very fluffy name has anti-inflammatory and antipyretic properties, and is used to treat inflammatory rheumatoid diseases and relieve acute pain. Its chemical name is N-(3-trifluoromethylphenyl)anthranilic acid, which doesn't sound quite as friendly and fluffy as its common name. In other languages it is called Flufenaminsäure (German), flufenaminezuur (Dutch), ácido flufenamico! (Spanish), and acide flufenamique (French).