Enzyme Nomenclature

Glossary of Chemical Names

The inevitable use of trivial names to describe enzyme reactions may have produced entries which are readily understood only by experts in that field. To help other readers, systematic chemical names are given below for many trivial names used in the enzyme list. The reader is reminded that the Compendium produced by the International Union of Biochemistry and Molecular Biology (Biochemical Nomenclature and Related Documents: Portland Press, London, 1992) includes detailed recommendations for amino acids, nucleic acids, lipids, steroids, carbohydrates, vitamins and other classes of biochemical compounds. Most compounds listed there are not repeated in this glossary.

The following list previously appeared in Enzyme Nomenclature, 1992. Additional glossary entries have been added from subsequent supplements and where relevant linked to separate entries showing the structure or reaction schemes where the structure is shown.

Details of systematic organic nomenclature may be found in the Nomenclature of Organic Chemistry A, B, C, D, E, F and H, issued by the Commission on the Nomenclature of Organic Chemistry (Pergamon Press, Oxford, 1979) and A Guide to IUPAC Nomenclature of Organic Chemistry, Recommendations 1993 (Blackwell Scientific Publications, 1993).

Fast move to entries starting with A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, Q, R, S, T, U, V, W, X, Y, Z.

(+)-abscisic acid (9Z)-(S)-6-hydroxy-3-oxo-11-apo-β-carotenoic acid
D(-)-acetoin (R)-3-hydroxybutan-2-one
N-acetylindoxyl N-acetylindol-3-ol
N-acetylisatin N-acetyl-1H-indole-2,3-dione
cis-aconitate (Z)-prop-1-ene-1,2,3-tricarboxylate
trans-aconitate (E)-prop-1-ene-1,2,3-tricarboxylate
acrolein prop-2-enal
acrylate prop-2-enoate
aculeacin A a cyclic peptide antibiotic*
adrenalin (R)-2-(methylamino)-1-(3,4-dihydroxyphenyl)ethanol
agaritine glutamic 5-[N'-[4-(hydroxymethyl)phenyl]hydrazine]
agarose a polysaccharide (structure)
agmatine (4-aminobutyl)guanidine
ajmalan an alkaloid*
alanopine meso-2,2'-iminodipropanoate
β-alanopine N-(D-1-carboxyethyl)-β-alanine
albendazole methyl [5-(propylthio)benzimidazol-2-yl]carbamate
alizarin 1,2-dihydroxyanthracene-9,10-dione
allantoate diureidoacetate
allantoin (2,5-dioxoimidazolidin-4-yl)urea
allyl alcohol prop-2-en-1-ol
amastatin Leu[1ψ2,CHOHCONH]ValValAsp
L-2-aminoadipate
  6-semialdehyde
(S)-2-amino-6-oxohexanoate
S-aminoethylcysteine
  ketimine
5,6-dihydro-2H-1,4-thiazine-3-carboxylate
S-2-aminomuconate
  6-semialdehyde
2-amino-6-oxohexa-2,4-dienoate
amygdalin 2-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)-2-phenylacetonitrile
androsterone 3α-hydroxy-5α-androstan-17-one
anhydrotetracycline an antibiotic*
anserine Nα-(β-alanyl)-Nπ-methylhistidine
anthranilate 2-aminobenzoate
anthrapurpurin 1,2,7-trihydroxyanthraquinone
arachidonate (all-Z)-icosa-5,8,11,14-tetraenoate
L-argininosuccinate Nω-[(S)-1,2-dicarboxyethyl]-L-arginine
aristolochene a sesquiterpenoid*
arogenate 3-(r-1-carboxy-c-4-hydroxycyclohexa-2,5-dien-1-yl) -L-alanine
arphamenine A Arg[1ψ2,COCH2]Phe
arphamenine B Arg[1ψ2,COCH2]Tyr
asparagusate 1,2-dithiolane-4-carboxylate
L-aspartate
  4-semialdehyde
(S)-2-amino-4-oxobutanoate
aspulvinone E 4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one
atropine tropine ester of (±)-tropate (see below)
azurin a blue copper protein found in many bacteria, which undergoes oxidation-reduction between Cu(I) and Cu(II), and transfers single electrons between enzymes
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bactoprenol 2,3-dihydroundecaprenol
barbituric acid pyrimidine-2,4,6-(1H,3H,5H)-trione
benzoin 2-hydroxy-1,2-diphenylethanone
benzyl viologen 1,1'-dibenzyl-4,4'-bipyridinium
berberine an alkaloid*
bergaptol 4-hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
betaine N,N,N-trimethylammonioacetate
betaine aldehyde N,N,N-trimethyl-2-oxoethylammonium
biochanin A 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-[1]benzopyran-4-one
biuret imidodicarbonic diamide
bleomycin an antibiotic*
(+)-borneol (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
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cadaverine pentane-1,5-diamine
trans-caffeate (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
caldesmon a protein
calmodulin a protein
(-)-1,2-campholide (1R,5R)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one
(+)-camphor (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
captopril (2S)-1-(3-mercapto-2-methyl-propanoyl)-L-proline
L-5-carboxymethyl-
  hydantoin
(S)-5-carboxymethylimidazolidine-2,4-dione
(-)-carnitine (R)-3-hydroxy-4-(trimethylammonio)butanoate
carnosine Nα-(β-alanyl)-L-histidine
(-)-casbene (2E,6E,10E)-(1R,14S)-3,7,11,1 5,15-pentamethylbicyclo[12.1.0]pentadeca-2,6,10-triene
catechol benzene-1,2-diol
cephalosporin C β-lactam antibiotic*
cetraxate 3-[4-(trans-4-methylaminocyclohexylcarbonyloxy)phenyl]propanoate
chalcone 1,3-diphenylprop-2-en-1-one
chlordecone 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
chlorogenate 5-caffeate ester of quinic acid (see below)
cholesterol cholest-5-en-3β-ol
choline (2-hydroxyethyl)trimethylammonium
chorismate (3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate
1,8-cineole 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, a monoterpenoid
cinnamyl alcohol 3-phenylprop-2-en-1-ol
(+)-citramalate (S)-2-hydroxy-2-methylbutanedioate
citrate 2-hydroxypropane-1,2,3-tricarboxylate
(+)-citronellol (R)-3,7-dimethyloct-6-en-1-ol
L-citrulline (S)-2-amino-5-ureidopentanoic acid
cocaine methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylate
codeine an alkaloid* (structure)
coenzyme-B N-(7-mercaptoheptanoyl)-L-threonine 3-O-phosphate (structure)
coenzyme M (CoM) 2-mercaptoethanesulfonate
coformycin (8R)-3-(β-D-ribofuranosyl)-3,5,7,8-tetrahydro-imidazo[4,5-d][1,3]diazepin-8-ol
columbamine an alkaloid*
compound E-64 (2S,3S)-3-(N-{(S)-1-[N-(4-guanidinobutyl)carbamoyl]3-methyl-
butyl}carbamoyl)oxirane-2-carboxylic acid (structure)
coniferin 4-(3-hydroxyprop-1-enyl)-2-methoxyphenyl β-D-glucopyranoside
coniferyl alcohol 3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ol
cortisol 11β,17,21-trihydroxypregn-4-ene-3,20-dione
cortisone 17,21-dihydroxypregn-4-ene-3,11,20-trione
4-coumaryl alcohol 3-(4-hydroxyphenyl)prop-2-en-1-ol
creatine (1-methylguanidino)acetate
creatinine 2-amino-1,5-dihydro-1-methylimidazol-4-one
crepenynic acid octadec-9-en-12-ynoic acid
crotonobetaine 4-(trimethylammonio)but-2-enoate
cucurbitacin a plant triterpenoid*
cumate 4-isopropylbenzoate
cyanuric acid 1,3,5-triazine-2,4,6(1H,3H,5H)-trione
cycasin (methyl-ONN-azoxy)methyl β-D-glucopyranoside
cyclopeptine an alkaloid*
cystathionine 2-amino-4[(2-amino-2-carboxyethyl)thio]butanoate
cystatin the protein inhibitor of cysteine endopeptidases from chicken egg-white
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daidzein 7-hydroxy-3-(4-hydroxyphenyl)-4H-[1]benzopyran-4-one
daphnin 7-(β-D-glucopyranosyloxy)-8-hydroxy-2H-1-benzopyran-2-one
12-dehydrotetracycline an antibiotic*
deoxycoformycin (8R)-3-(2-deoxy-β-D-erythro-pentafuranosyl)-3,5,7,8-tetrahydro-
  imidazo[4,5-d][1,3]diazepin-8-ol
11-deoxycorticosterone 21-hydroxypregn-4-ene-3,20-dione
deoxyhypusine N6-(4-aminobutyl)lysine
desmosterol cholesta-5,24-dien-3β-ol
2,6-dichloroindophenol 4-(2,6-dichloro-4-hydroxyphenylimino)cyclohexa-2,5-dien-1-one
desmycosin a macrolide antibiotic*
destomycin an antibiotic*
meso-2,6-diamino-
  pimelate
(2R,6S)-2,6-diaminoheptanedioate
7,8-dihydrobiopterin 2-amino-7,8-dihydro-6-[(1S,2R)-1,2-dihydroxypropyl ]-1H-pteridin-4-one
dihydrodipicolinate (2S)-2,3-dihydropyridine-2,6-dicarboxylate
2,3-dihydropicolinate 2,3-dihydropyridine-2-carboxylate
7,8-dihydroxy-
  kynurenate
4,7,8-trihydroxyquinoline-2-carboxylate
(+)-2,5-diketocamphane (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2,5-dione
dimethylmaleate (Z)-2,3-dimethylbut-2-enedioate
S,S-dimethyl-
  -β-propiothetin
3-(dimethylsulfonio)propanoate
diphthamide 2-[3-carbamoyl-3-(trimethylammonio)propyl]-L-histidine
diphthine 2-[3-carboxy-3-(trimethylammonio)propyl]-L-histidine
dipicolinate pyridine-2,6-dicarboxylate
dolichol 2,3-dihydropolyprenol (C55-C100)
L-dopa (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
dopachrome 2,3,5,6-tetrahydro-5,6-dioxo-1H-indole-2-carboxylate
dopaquinone (S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate
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E64 (2S,3S)-3-(N-{(S)-1-[N-(4-guanidinobutyl)carbamoyl]3-methyl-
butyl}carbamoyl)oxirane-2-carboxylic acid (structure)
α-ecdysone (22R)-2β,3β,14,22,25-pentahydroxy-5β-cholest-7-en-6-one
emodin 1,3,8-trihydroxy-6-methylanthraquinone
(-)-ephedrine (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
ergosterol (22E,24S)-24-methylcholesta-5,7,22-trien-3β-ol
eriodictyol (S)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-chromen-4-one
erythromycin a macrolide antibiotic*
erythronolide an antibiotic*
estradiol-17α estra-1,3,5(10)-triene-3,17α-diol
estradiol-17β estra-1,3,5(10)-triene-3,17β-diol
estriol estra-1,3,5(10)-triene-3,16α,17β-triol
estrone 3-hydroxyestra-1,3,5(10)-trien-17-one
ethanolamine 2-aminoethan-1-ol
etiocholanolone 3α-hydroxy-5β-androstan-17-one
farnesol 3,7,11-trimethyldodeca-2,6,10-trien-1-ol
(–)-α-fenchol (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
(+)-fenchone (1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
ferulate 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
fibronectin a glycoprotein
ficaprenol tri-trans,poly-cis-undecaprenol
fluorene cyclopenta[1,2:3,4]dibenzene
formononetin 7-hydroxy-3-(4-methoxyphenyl)-4H-[1]benzopyran-4-one
fucosterol (24E)-24-ethylidenecholest-5-en-3β-ol
4-fumarylacetoacetate (E)-4,6-dioxooct-2-enedioate
3-fumarylpyruvate (E)-4,6-dioxohept-2-enedioate
fusarinine N5-(cis-5-hydroxy-3-methylpent-2-enoyl)-N5-hydroxy-L-ornithine
fusarinine C a cyclic trihydroxamic acid formed by esterification of 3 molecules of fusarinine
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gallate 3,4,5-trihydroxybenzoate
genistein 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-[1]benzopyran-4-one
gentisate 2,5-dihydroxybenzoate
(+)-geodin methyl
  5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-
  spiro[benzofuran-2(3H),1'-cyclohexa-2',5'-diene]-2'-carboxylate
geraniol (E)-3,7-dimethylocta-2,6-dien-1-ol
germacrene A a sesquiterpenoid* (structure)
gibberellin a terpenoid* (structure)
globomycin an antibiotic*
glucotropeolin β-D-glucosyl 2-phenylthioacetohydroximate O-sulfate
glutaconate pent-2-enedioate
L-glutamate
  5-semialdehyde
(S)-2-amino-5-oxopentanoate
glutarate
   semialdehyde
5-oxopentanoate
glutathionylspermidine N1-(γ-L-glutamyl-L-cysteinyl-glycyl)-spermidine
glyceollin I (6aS,11bR)-2,2-dimethyl-2H,6H-benzofuro[3,2-c]-
  pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol
sn-glycerol 3-phosphate (R)-glycerol 3-phosphate
glycerone 1,3-dihydroxypropan-2-one
glycolaldehyde 2-hydroxyethanal
glycolate 2-hydroxyacetate
glycyrhizinate a terpenoid*
glycyrrhetinate a terpenoid*
glyoxylate 2-oxoacetate
guaiacol 2-methoxyphenol
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hepoxilin A3 (5Z,9E,14Z)-(8,11R,12S)-11,12 -epoxy-8-hydroxyicosa-5,9,14-trienoate
heteropyrithiamin 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyridinium
hippurate N-benzoylglycine
homogentisate (2,5-dihydroxyphenyl)acetate
sym-homospermidine N-(4-aminobutyl)butane-1,4-diamine
humulene (1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene
hydroxyacetone
  phosphate
2-oxopropyl phosphate
(+)-5-exo-hydroxy-
  camphor
(1R,4R,5R)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-one
2-hydroxy-3-carboxy-
  adipate
1-hydroxybutane-1,2,4-tricarboxylate
4-hydroxycatechol benzene-1,2,4-triol;
1,2,4-trihydroxybenzene
2-hydroxy-4-methyl-
  -3-carboxyvalerate
2-hydroxy-3-isopropylbutanedioate
3α-hydroxy-
  5β-cholanate
3α-hydroxy-5β-cholan-24-oate
4-hydroxyhydratropate 2-(4-hydroxyphenyl)propanoate
3-hydroxyisobutyrate 3-hydroxy-2-methylpropanoate
6-hydroxymellein (R)-3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin
2-hydroxymuconate semialdehyde 2-hydroxy-6-oxohexa-2,4-dienoate
2-hydroxyquinoline quinolin-2-ol exists largely as the quinolin-2(1H)-one tautomer.
4-hydroxyquinoline quinolin-4-ol exists largely as the quinolin-4(1H)-one tautomer.
D-2-hydroxystearate (R)-2-hydroxyoctadecanoate
hygromycin B an antibiotic*
L-hyoscyamine an alkaloid*
hyponitrous acid HO-N=N-OH
hypotaurine 2-aminoethanesulfinate
hypotaurocyamine 2-guanidinoethanesulfinate
hypusine N6-[(R)-4-amino-2-hydroxybutyl]-L-lysine
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inulobiose D-fructosyl-2,1-α-D-fructose
isochorismate (5S,6S)-5-[(1-carboxyvinyl)oxy]-6-hydroxycyclohexa -1,3-diene-1-carboxylate
isocitrate 1-hydroxypropane-1,2,3-tricarboxylate. Unless stated otherwise, the isomer involved is (1R,2S)-1-hydroxypropane-1,2,3-tricarboxylate, formerly called threo-DS-isocitrate
isolychnose O-α-D-galactopyranosyl-(1[arrow right]3)-β-D-fructofuranosyl
  O-α-D-galactopyranosyl-(1[arrow right]6)-α-D-glucopyranoside
isonocardicin A a β-lactam antibiotic*
isophenoxazine 2-amino-3H-phenoxazin-3-one
(-)-trans-isopiperitenol (1S,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-ol
isowillardiine 3-(uracil-3-yl)-L-alanine
itaconate 2-methylenebutanedioate
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jasmonate 2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetate
juglone 5-hydroxynaphthalene-1,4-dione
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kaempferol 3,5,7-trihydroxy-2-(4-hydroxphenyl)-4H-[1]-benzopyran-4-one
kievitone 3-(2,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
kievitone hydrate 3-(2,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-hydroxy-3-methylbutyl)chromen-4-one
kynurenate 4-hydroxyquinoline-2-carboxylate
L-kynurenine 3-(2-aminobenzoyl)-L-alanine
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L-lactaldehyde (S)-2-hydroxypropanal
L-lactate (S)-2-hydroxypropanoate
lactenosin a macrolide antibiotic*
lanosterol 4,4,14-trimethyl-5α-cholesta-8,24-dien-3β-ol
leucopelargonidin 3,4-dihydro-2-(4-hydroxyphenyl)-2H-[1]benzopyran-3,4,5,7- tetrol
licodione 2,4,4'-trihydroxydibenzoylmethane
limonene (4S)-1-methyl-4-isopropenylcyclohex-1-ene (structure)
α-linolenate (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
γ-linolenate (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
linalool 3,7-dimethylocta-1,6-dien-3-ol
linamarin 2-(β-D-glucopyranosyloxy)-2-methylpropanenitrile
linoleate (9Z,12Z)-octadeca-9,12-dienoate
γ-linolenate (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
lipoamide 5-(1,2-dithiolan-3-yl)pentanamide
lipoate 5-(1,2-dithiolan-3-yl)pentanoate
lombricine O3-([2-guanidinoethoxy]phosphono)-L-serine
lophenol 4α-methyl-5α-cholesta-7-en-3β-ol
lumazine 1H,3H-pteridine-2,4-dione
lumichrome 7,8-dimethyl-1H,3H-benzo[g]pteridine-2,4-di one
lupinate (S)-2-amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoate (structure)
luteolin 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
lychnose O-α-D-galactopyranosyl-(1[arrow right]1)-O-β-D-fructofuranosyl
  O-α-D-galactopyranosyl-(1[arrow right]6)-α-D-glucopyranoside
D-lysopine N2-(D-1-carboxyethyl)-L-lysine
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maackiain (6aR,12aS)-6a,12a-dihydro-6H-[1,3]dioxolo[5 ,6]-
  benzofuro[3,2-c][1]benzopyran-3-ol
macrocin a macrolide antibiotic*
L-malate (S)-2-hydroxybutanedioate
maleamate (Z)-3-carbamoylprop-2-enoate
2-maleylacetate (Z)-4-oxohex-2-enedioate
4-maleylacetoacetate (Z)-4,6-dioxooct-2-enedioate
3-maleylpyruvate (Z)-4,6-dioxohept-2-enedioate
malonate semialdehyde 3-oxopropanoate
L-mandelate (S)-2-hydroxy-2-phenylacetate
mandelonitrile 2-hydroxy-2-phenylacetonitrile
medicarpin (6aR,11aS)-6a,11a-dihydro-9-methoxy-
  -6H-benzofurano[3,2-c][1]benzopyran-3-ol
melatonin N-acetyl-2-(5-methoxyindol-3-yl)ethylamine
melilotate 3-(2-hydroxyphenyl)propanoate
menadione 2-methyl-1,4-naphthoquinone
(-)-menthol (1R,2S,5R)-2-isopropyl-5-methylcyclohexanol
mesaconate (E)-2-methylbut-2-enedioate
methanofuran 4-[N-(4,5,7-tricarboxyheptanoyl)-γ-L-glutamyl-γ-L-glutamyl-4-(2-aminoethyl)-
  phenoxymethyl]-2-(aminomethyl)furan
methanopterin 1-O-[2,3,4-trihydroxy(4-{[1-(2-amino-1,4-dihydro-7-methyl-4-oxopteridin-6-yl)-
  ethyl]amino}phenyl)-pentyl]-α-D-ribofuranose 5[(1,3-dicarboxypropyl) phosphate
methylglyoxal 2-oxopropanal
N-methylhydantoin 1-methylimidazolidene-2,4-dione
methylitaconate 2-methyl-3-methylenebutanedioate
methylmalonate semialdehyde 2-methyl-3-oxopropanoate
3-methyloxindole 1,3-dihydro-3-methylindol-2-one
methyl viologen 1,1'-dimethyl-4,4'-bipyridinium
mevaldate 3-hydroxy-3-methyl-5-oxopentanoate
(-)-mevalonate (R)-3,5-dihydroxy-3-methylpentanoate
L-mimosine 3-(3-hydroxy-4-pyridon-1-yl)-L-alanine
morphine an alkaloid* (structure)
morphinone an alkaloid* (structure)
cis,cis-muconate (2Z,4Z)-hexa-2,4-dienedioate
mycocerosate a fatty acid with a methyl branch
mycothiol 1-O-(2-[N-acetyl-L-cysteinyl]amido-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol (structure)
mycothione oxidized (disulfide) form of mycothiol
myrcene 7-methyl-3-methyleneocta-1,6-diene (structure)
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naloxone an alkaloid*
naringenin chalcone 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-prop-2-en-1-one
(+)-neomenthol (1S,2S,4R)-2-isopropyl-5-methylcyclohexanol
nerol (Z)-3,7-dimethylocta-2,6-dien-1-ol
NHMec 7-(4-methyl)coumarylamide
L(-)-nicotine (S)-3-(N-methylpyrrolidin-2-yl)pyridine
nocardicin A a β-lactam antibiotic*
D-nopaline N2-(D-1,3-dicarboxypropyl)-L-arginine
noradrenalin 2-amino-1-(3,4-dihydroxyphenyl)ethanol
norcoclaurine an alkaloid* (structure)
(+)-norephedrine (1S,2R)-2-amino-1-phenylpropan-1-ol
normorphine an alkaloid*
norvaline 2-aminopentanoic acid
nuatigenin (20S,22S,25S)-22,25-epoxyfurost-5-ene-3β,26-diol
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obtusifoliol 4α,14α-dimethyl-5α-ergosta-8,24(28)-dien-3β-ol or 4α,14α-dimethyl-24-methylene-5α-cholesta-8-en-3β-ol
D-octopine N2-(D-1-carboxyethyl)-L-arginine
oleandomycin a macrocyclic antibiotic*
oleate (Z)-octadec-9-enoate
orcinol 5-methylbenzene-1,3-diol
organyl Any organic substituent group, regardless of functional type, having one free valence at a carbon atom
orotate 1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylate
orsellinate 2,4-dihydroxy-6-methylbenzoate
4-oxalmesaconate 4-oxobut-1-ene-1,2,4-tricarboxylate
oxaloacetate 2-oxobutanedioate
oxalocrotonate 5-oxohex-2-enedioate
oxaloglycolate 2-hydroxy-3-oxobutanedioate
oxalomalate 1-hydroxy-3-oxopropane-1,2,3-tricarboxylate
oxalureate 2-oxo-2-ureidoacetate
oxidized glutathione The term 'oxidized glutathione' has been replaced by the term 'glutathione disulfide' as the former is ambiguous. S,S'-Biglutathione may also be used to refer to this compound
oxidized thioredoxin The term 'oxidized thioredoxin' has been replaced by 'thioredoxin disulfide' as the former is ambiguous
5-oxo-1,2-campholide (1R,5R)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octane- 3,6-dione
(+)-6-oxocineole (1S,4R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one
2-oxoisocaproate 6-methyl-2-oxoheptanoate
2-oxosuccinamate 3-carbamoyl-2-oxopropanoate
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palatinose isomaltulose
pantetheine amide of pantothenate (see below) with 3-aminopropane-1-thiol
(R)-pantoate (R)-2,4-dihydroxy-3,3-dimethylbutanoate
pantothenate amide of pantoate (see above) with 3-aminopropanoate
pantoyl lactone (R)-2-hydroxy-3,3-dimethylbutan-4-olide
PAPS 3'-phosphoadenylyl sulfate (structure)
paraoxon diethyl 4-nitrophenyl phosphate
pentalenene (1R,3aS,5aS,8aR)-1,2,3,3a,5a,6,7,8-octahydro-
  -1,4,7,7-tetramethylcyclopenta[c]pentalene
pepstatin isovaleryl-L-valyl-L-valyl-4-amino-3-hydroxy-6-methyl-
  heptanoyl-L-alanyl-4-amino-3-hydroxy-6-methylheptanoic acid
perillyl alcohol mentha-1,8-dien-7-ol
phenazine methosulfate 5-methylphenazinium methyl sulfate
phenosafranin 3,7-diamino-5-phenylphenazinium
phloretate 3-(4-hydroxyphenyl)propanoate
phloretin 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-propan-1-one
phloroglucinol benzene-1,3,5-triol
phorbol a diterpenoid* (structure)
phosphoenolpyruvate 2-(phosphonooxy)prop-2-enoate
phytanate 3,7,11,15-tetramethylhexadecanoate
phytodienoate 8-{(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-enyl}octanoate
pimelic acid heptanedioic acid
pinene (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (structure)
L-pipecolate (S)-piperidine-2-carboxylate
trans-piperitenol (1R,6R)-6-isopropyl-3-methylcyclohex-2-en-1-ol
planteose O-α-D-galactopyranosyl-(1[arrow right]6)-β-D-fructofuranosyl-
  -αD-glucopyranoside
porphyran a polysaccharide (structure)
pregnenolone 3β-hydroxypregn-5-en-20-one
prephenate 3-(r-1-carboxy-c-4-hydroxycyclohexa-2,5-dien-1-yl)-2-oxopropanoate
presqualene diphosphate [(1R,2R,3R)-2-[(E)-4,8-dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-
  -2,6,10-trimethylundeca-1,5, 9-trienyl]cyclopropan-1-yl] methyl diphosphate (structure)
pretyrosine 3-(r-1-carboxy-c-4-hydroxycyclohexa-2,5-dien-1-yl)-
  -L-alanine (also called arogenate)
primeverose 6-O-(β-D-xylopyranosyl)-D-glucose
progesterone pregn-4-ene-3,20-dione
protocatechuate 3,4-dihydroxybenzoate
2-protocatechuoyl-
  phloroglucinolcarboxylate
2,4-dihydroxy-6-(3,4-dihydroxybenzoyloxy)benzoate
L-prunasin (S)-2-(β-D-glucopyranosyloxy)-2-phenylacetonitrile
pseudobaptigenin 3-(1,3-benzodioxol-5-yl)-7-hydroxy-[1]benzopyran-3-one
(+)-pseudoephedrine (1S,2S)-2-methylamino-1-phenylpropan-1-ol
pseudotropine exo-8-methyl-8-azabicyclo[3.2.1]octan-3-ol
psychosine (E)-(2R,3S)-2-amino-3-hydroxyoctadec-4-enyl β-D-galactopyranoside
pterocarpan (6aR,11aR)-6a,11a-dihydro-6H-benzofuro[3,2-c]-[1]benzopyran
(+)-trans-pulegol (1S,5R)-2-isopropylidene-5-methylcyclohexan-1-ol
pullulan A linear polymer of 1,6-linked maltotriose units.
putrescine butane-1,4-diamine
pyrimidodiazepine 6-acetyl-2-amino-8,9-dihydro-3H-pyrimido[4,5-b]-[1,4]diazepin-4-one
pyrogallol benzene-1,2,3-triol
L-pyroglutamate 5-oxo-L-proline
pyruvate 2-oxopropanoate
6-pyruvoyltetrahydropterin 1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2- dione
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quercetagetin 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-[1]benzopyran-4-one
quercetin 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-[1]benzopyran-4-one
quercitrin quercetin 3-rhamnoside
questin 1,6-dihydroxy-8-methoxy-3-methylanthraquinone
(-)-quinate (3R,5R)-1(OH),3,4/5-tetrahydroxycyclohexanecarboxylate (structure)
quinine an alkaloid (structure)
quinizarin 1,4-dihydroxyanthraquinone
quisqualic acid 3-(3,5-dioxo-1,2,4-oxazadiazolidin-2-yl)Ala
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raucaffricine an alkaloid*
Rieske cluster A [2Fe-2S] cluster having Cys2 coordination at one iron, and His2 coordination at the other
resveratrol (E)-stilbene-3,4',5-triol
reticulene an alkaloid*
ricinine 1,2-dihydro-4-methoxy-N-methyl-2-oxopyridine-3-carbonitrile
ricinoleic acid (9Z,12R)-12-hydroxyoctadec-9-enoic acid
rosmarinic acid 3-(3,4-dihydroxycinnamoyloxy)-3-(3,4-dihydroxy-phenyl)propanoic acid
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sabinene hydrate 2-methyl-5-isopropylbicyclo[3.1.0]hexan-2-ol
(+)-cis-sabinol (1S,3R,5S)-1-isopropyl-4-methylenebicyclo[3.1.0]hexan-3-ol
saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine
salicin 2-(hydroxymethyl)phenyl β-D-glucopyranoside
α-santonin a sesquiterpenoid*
sarcosine N-methylglycine
sarsapogenin (25S)-5β-spirostan-3β-ol
scoulerene an alkaloid* (structure)
scytalone 3,4-dihydro-3,6,8-trihydroxynaphthalen-1(2H)-one
secologanin methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyl-
  oxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate
sepiapterin 1-(2-amino-7,8-dihydro-4-hydroxypteridine-6-yl)-2-hydroxypropan-1-one
serotonin 3-(2-aminoethyl)-1H-indol-5-ol
(-)-shikimate (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
sinapate 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
sinapyl alcohol 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-ol
solanesol all-trans-nonaprenol
spermidine N-(3-aminopropyl)butane-1,4-diamine
spermine N,N'-bis(3-aminopropyl)butane-1,4-diamine
spiramycin a macrolide antibiotic*
squalene (all-E)-2,6,10,15,19,23-hexamethyltetraicosa-2,6,10,14,18,22-hexaene
stearate octadecanoate
sterigmatocystin 3a,12c-dihydro-8-hydroxy-6-methoxyfuro[3',2':4,5]furo[2,3-c]xanthen-7-one
stilbene 1,2-diphenylethene (or styrylbenzene)
stipitatate 3,6-dihydroxy-5-oxocyclohepta-1,3,6-triene-1-carboxylate
stipitatonic acid 4,7-dihydroxy-1H-cyclohepta[c]furan-1,3,6-trione
3-α(S)-strictosidine an alkaloid*
L-strombine N-(carboxymethyl)-L-alanine
succinate semialdehyde 4-oxobutanoate
sulcatol 6-methylhept-5-en-2-ol
sulcatone 6-methylhept-5-en-2-one
sulfoacetaldehyde 2-oxoethylsulfonate
sulochrin methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate
superoxide O2-
(-)-sympatol (R)-1-(4-hydroxyphenyl)-2-methylaminoethan-1-ol
synephrine 1-(4-hydroxyphenyl)-2-(methylamino)ethanol
syringin 4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenyl β-D-glucopyranoside
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tabersonine an alkaloid*
L(+)-tartrate (2R,3R)-2,3-dihydroxybutanedioate
tartronate semialdehyde 2-hydroxy-3-oxopropanoate
taurine 2-aminoethanesulfonate
taurocyamine 2-guanidinoethanesulfonate
tauropine N2-(D-1-carboxyethyl)-2-aminoethanesulfonate
taxiphyllin 2-(β-D-glucopyranosyloxy)-2-(4-hydroxyphenyl)acetonitrile
testololactone β3-oxo-13,17-secoandrost-4-ene-17,13α-lactone
testosterone 17β-hydroxyandrost-4-en-3-one
tetrahydroberberine an alkaloid*
tetrahydrocolumbamine an alkaloid*
L-thalassemine N,N-dimethyl-O3-([2-guanidinoethoxy]phosphono)-L-serine
theanine N5-ethyl-L-glutamine
thetin S,S-dialkyl-1,2λ4-oxothietan-4-one, i.e. dimethylsulfonioacetate
(+)-thujan-3-ol (1S,3S,4S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol
(-)-thujol (1S,3S,4R,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol
tigloate trans-2-methylbut-2-enoate
triacetate lactone 4-hydroxy-6-methylpyran-2-one
trichodiene a terpenoid*
trioxilin A3 8,11,12-trihydroxyicosa-5,9,14-trienoate
(-)-tropate (S)-2-(hydroxymethyl)-2-phenylacetate
tropine (3R)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol
tropinone 8-methyl-8-azabicyclo[3.2.1]octan-3-one
trypanothione disulfide the oxidized form of N1,N8-bis(glutathionyl)-spermidine
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umbelliferone 7-hydroxy-1-benzopyran-2-one
ureidoglycolate 2-hydroxy-2-ureidoacetate
uric acid 7,9-dihydro-1H-purine-2,6,8(3H)-trione
urocanate 3-(1H-imidazol-4-yl)prop-2-enoate
L-usnic acid (S)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-dibenzofuran-1(9bH)-one (structure)
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5-valerolactone pentan-5-olide
validamine 1-amino-1,5,6-trideoxy-5-(hydroxymethyl)-D-chiro-inositol
vanillate 4-hydroxy-3-methoxybenzoate
vanillin 3-hydroxy-4-methoxybenzaldehyde
vermelone 3,4-dihydro-3,8-dihydroxynaphthalen-1(2H)-one
vernolic acid (9Z,12S,13R)-12,13-epoxyoctadec-9-enoic acid
vestitone 2,3-dihydro-7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-[1]benzopyran-4-one
vicianin (R)-2-(6-O-α-L-arabinopyranosyl-β-D-glucopyranosyloxy)-2-phenylacetonitrile
vicianose 6-O-(α-L-arabinopyranosyl)-D-glucose
vindoline an alkaloid*
vomifoliol (6R,9S)-6,9-dihydroxy-9-apo-ε-caroten-3-one
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warfarin 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-[1]benzopyran-2-one
willardiine 3-(uracil-1-yl)-L-alanine
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xanthommatin 2-amino-4-(3-carboxy-1-hydroxy-5-oxo-5H-pyrido[3,2-a]phenoxazine-11-yl)-
  -4-hydroxybutanoate
xanthopterin-B2 1-(7,8-dihydro-2,4-dihydroxypteridin-6-yl)-2-hydroxypropan-1-one
xanthotoxol 9-hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
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zeatin 2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol (structure)
zymostrol 5α-cholesta-8,24-dien-3β-ol

*Many alkaloids, antibiotics and terpenoids, such as those marked with an asterisk, have structures that are too complex for a systematic name to be given in tabular form. The reader is referred to the standard dictionaries of these compounds, such as:

Bycroft, B.W.(Ed.), Dictionary of antibiotics and related substances, Chapman and Hall, 1987.

Collins, P.M. Carbohydrates, Chapman and Hall, 1987.

Glasby, J.S. Encyclopedia of the Alkaloids, Plenum Press, 1975-1983.

Glasby, J.S. Encyclopedia of Antibiotics, 2nd edn., Wiley, 1979.

Glasby, J.S. Encyclopedia of the Terpenoids, Wiley, 1983.


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