NYMPHAEOL A

A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy group at positions 5, 7, 3' and 4' and a geranyl group at position 6. Isolated from Macaranga tanarius and propolis collected in Okinawa, it exhibits radical scavenging activity.


NYMPHAEOL B

A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy group at positions 5, 7, 3' and 4' and a geranyl group at position 2'. Isolated from Macaranga tanarius and propolis collected in Okinawa, it exhibits radical scavenging activity.


NYMPHAEOL C

A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy group at positions 5, 7, 3' and 4', a geranyl group at position 2' and a prenyl group at position 6. Isolated from Macaranga tanarius and propolis collected in Okinawa, it exhibits radical scavenging activity.


maackiaflavanone A

A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 2', a methoxy group at position 7, a prenyl group at position 8 and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 4' and 5'. Isolated from the stem barks of Maackia amurensis, it exhibits cytotoxicity against human cancer cell lines.


maackiaflavanone B

A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 7, prenyl groups at positions 8 and 3' and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 4' and 5'. Isolated from the stem barks of Maackia amurensis, it exhibits cytotoxicity against human cancer cell lines.


maackiapterocarpan A

A member of the class of pterocarpans that is pterocarpan substituted by a hydroxy group at position 3, a methylenedioxy group across positions 8 and 9 and a 2,2-dimethyltetrahydro-2H-pyran ring fused across positions 1 and 2 (the 8aR,14aR stereoisomer). Isolated from the stem barks of Maackia amurensis,it exhibits cytotoxicity against human cancer cell lines.


macabarterin

A ellagitannin isolated  from the stem bark of Macaranga barteri and has been shown to exhibit anti-inflammatory activity.


MACAFLAVANONE G

A trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 4', a prenyl group at position 6 and a (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)tetrahydro-2H-pyran ring fused across positions 2' and 3'. Isolated from the leaves of Macaranga tanarius, it exhibits antineoplastic activity.


macaranone A

A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 7, 3' and 4', a geranyl group at position 2' and a prenyl group at position 5'. Isolated from the leaves of Macaranga sampsonii, it exhibits cytotoxicity against several human cancer cell lines.


MACLURAXANTHONE B

A member of the class of xanthones  that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3, 6 and 7, a dimethylallyl group at position 2 and a prenyl group at position 4. Isolated from Maclura tinctoria and Cudrania tricuspidata, it exhibits anti-HIV and antineoplastic activity.


MACLURAXANTHONE C

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3, 5 and 6, a dimethylallyl group at position 2 and a prenyl group at position 4. Isolated from Maclura tinctoria and Cudrania tricuspidata, it exhibits anti-HIV and antineoplastic activity.


madecassoside

A triterpenoid saponin that is a trisaccharide derivative of madecassic acid. Isolated from    Centella asiatica, it exhibits anti-inflammatory, antioxidant and antirheumatic activities.


madhucoside A

A triterpenoid saponin that consists of protobassic acid as the aglycone moiety. Isolated from the barks of Madhuca indica, it exhibits radical scavenging activity.


(+)-makassaric acid

A meroterpenoid isolated from the marine sponge Acanthodendrilla sp. It exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7.11.1).


mallotophilippen A

A chromenol that is 2H-chromene-5,7-diol substituted by geminal methyl groups at position 2, a 2-methylbutanoyl group at position 8 and a 2,4,6-trihydroxy-3-methyl-5-(2-methylpropanoyl)benzyl group at position 6. Isolated from Mallotus philippensis, it exhibits anti-inflammatory activity.


mallotophilippen B

A chromenol that is 2H-chromene-5,7-diol substituted by geminal methyl groups at position 2, a 2-methylbutanoyl group at position 8 and a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6. Isolated from Mallotus philippensis, it exhibits anti-inflammatory activity.


mallotophilippen C

A member of the class of chalcones that is chalcone substituted by hydroxy groups at positions 4, 2' and 4', a geranyl group at position 3' and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 5' and 6'. Isolated from the fruits of Mallotus philippensis, it exhibits anti-inflammatory and immunoregulatory activities.


mallotophilippen D

A member of the class of chalcones that is chalcone substituted by hydroxy groups at positions 3, 4, 2' and 4', a geranyl group at position 3' and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 5' and 6'. Isolated from the fruits of Mallotus philippensis, it exhibits anti-inflammatory and immunoregulatory activities.


(RS)-mallotophilippen E

A racemate composed of equimolar quantities of R- and S- mallotophilippen E. Isolated from the fruits of Mallotus philippensis, it exhibits anti-inflammatory and immunoregulatory activities.


A member of the class of chromenes that is 2H-chromene substituted by geminal methyl groups at position 2, methoxy groups at positions 5 and 7 and a (3R)-3-hydroxybutanoyl group at position 6. Isolated from the leaves of Mallotus apelta, it exhibits antineoplastic activity.


A member of the class of chromenes that is 2H-chromene substituted by geminal methyl groups at position 2, methoxy groups at positions 5 and 7 and a (3R)-3-methoxybutanoyl group at position 6. Isolated from the leaves of Mallotus apelta, it exhibits antineoplastic activity.


6alpha-malonyloxymanoyl oxide

The malonate ester of a labdane diterpenoid. Isolated from the aerial parts of Stemodia foliosa, it exhibits antibacterial activity.


manassantin A

A lignan isolated from Saururus cernuus and Saururus chinensis and has been shown to exhibit antineoplastic activity.


MANIOSIDE A

A steroid saponin that consists of pennogenin attached to alpha-L-rhamnopyranosyl-(1->3)-beta-D-glucopyranosyl residue at position 3 via a glycoidic linkage. Isolated from Dracaena mannii, it exhibits anti-inflammatory activity.


MANOALIDE

A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.


MANZAMINE A

An alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).


MANZAMINE Y

An alkaloid that is manzamine A with a hydroxy substituent at position 6. Isolated from Haliclona and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).


8-hydroxymanzamine A

An alkaloid that is manzamine A with a hydroxy substituent at position 8. Isolated from Pachypellina and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).


maoecrystal Z

A tetracyclic diterpenoid isolated from the leaves of a Chinese medicinal herb Isodon eriocalyx and has been shown to exhibit cytotoxicity towards human tumour cells.


A  pentacyclic triterpenoid that is the  benzoate ester obtained by the condensation of the 3-hydroxy group of 1beta-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits  inhibitory activity against HIV-1 reverse transcriptase.


A  pentacyclic triterpenoid that is the diester obtained by the condensation of the hydroxy groups of 2alpha-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits inhibitory activity against HIV-1 reverse transcriptase.


marianine

A  tetracyclic triterpenoid  that is lanost-8-ene substituted by hydroxy groups at positions 3 and 25, a methylidene group at position 24 and an oxo group at position 7. Isolated from the whole plant of Silybum marianum, it exhibits inhibitory activity against  chymotrypsin.


marianoside A

A triterpene glycoside that is lanost-8-ene substituted by hydroxy groups at positions 25 and 28, a methylidene group at position 24 and a beta-D-glucopyranosyloxy group at position 3. Isolated from the whole plant of Silybum marianum, it exhibits inhibitory activity against chymotrypsin.


marianoside B

A triterpene glycoside that is lanost-8-ene substituted by a methylidene group at position 24 and a beta-D-glucopyranosyloxy group at position 3. Isolated from the whole plant of Silybum marianum, it exhibits inhibitory activity against chymotrypsin.


MARINEOSIN A

A macrocycle isolated from a marine sediment-derived actinomycete, Streptomyces sp. It exhibits cytotoxicity against colon tumour cell lines.


marineosin B

A macrocycle isolated from a marine sediment-derived actinomycete, Streptomyces sp. A stereoisomer of marineosin A, it exhibits cytotoxicity against colon tumour cell lines.


(-)-marinopyrrole A

A member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities.


(-)-marinopyrrole B

A member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by a bromo group at position 3, four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities.


CARPUSIN

A member of the class of 1-benzofurans that is 1-benzofuran-3(2H)-one, substituted by hydroxy groups at positions 2 and 6, a 4-hydroxybenzyl group at position 2 and a methoxy group at position 4. Isolated from the heartwood of   Pterocarpus marsupium, it exhibits antihyperglycemic and antihyperlipidemic activities.


martefragin A

An indole alkaloid isolated from the red alga Martensia fragilis and has been shown to inhibit lipid peroxidation.


MASLINIC ACID

A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity.


epi-maslinic acid

A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of  maslinic acid. Isolated from  Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity.


A guanidinium ion that is a conjugate acid of massadine.


matsudone A

A glycosyloxyflavone that is 5,3',4'-trihydroxyflavone substituted by a beta-D-glucopyranosyloxy group at position 3 and a 2'',2''-dimethylpyrano ring fused across positions 7 and 8. Isolated from the leaves of Salix matsudana, it acts as a cyclooxygenase 2 inhibitor.


maytenfolone A

A hexacyclic triterpenoid that is a lactone of friedelin. Isolated from Celastrus hindsii, it exhibits anti-HIV and antineoplastic activities.


mediomycin A

A polyene antibiotic isolated from Streptomyces mediocidicus ATCC23936 and has been shown to exhibit a broad spectrum of antifungal activity.


megathyrin A

A cyclic terpene ketone that is ent-7alpha,20-epoxy-kaur-16-en-15-one substituted with hydroxy groups at positions 1, 7 and 14 (the 1alpha,7beta,14beta stereoisomer). Isolated from  the leaves of Isodon megathyrsus, it exhibits cytotoxic activity.


melemeleone B

A sesquiterpenoid with a quinone and taurine functionality. It is isolated from the sponge Dysidea avara, and exhibits inhibitory activity against tyrosine kinase.


melophlin P

A member of the class of pyrrolidin-2-ones that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxyhexadecylidene moiety at position 3. Isolated from the marine sponge Melophlus sarasinorum and other species of genus Melophlus, it exhibits cytotoxicity against murine leukemia cell line.


MELOPHLIN Q

A pyrrolidinone that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-13-methyltetradecylidene moiety at position 3. Isolated from the marine sponge Melophlus sarasinorum and other species of genus Melophlus, it exhibits cytotoxicity against murine leukemia cell line.


MELOPHLIN R

A member of the class of pyrrolidin-2-ones that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-12-methyltetradecylidene moiety at position 3. Isolated from the marine sponge Melophlus sarasinorum and other species of genus Melophlus, it exhibits cytotoxicity against murine leukemia cell line.


melophlin S

A member of the class of pyrrolidin-2-ones that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-5-methyltetradecylidene moiety at position 3. Isolated from the marine sponge Melophlus sarasinorum and other species of genus Melophlus, it exhibits cytotoxicity against murine leukemia cell line.


metachromin S

A sesquiterpenoid that is 5-amino-2-hydroxy-3-methyl-1,4-benzoquinone in which one of the hydrogens of the methyl group is replaced by a 2-methyl-4-[(1R,2S)-1,2,3-trimethylcyclohex-3-en-1-yl]but-1-en-1-yl group and one of the hydrogens attached to the nitrogen is replaced by a 3-methylbutyl group. It is isolated from an Okinawan sponge Spongia sp.SS-1037 and exhibits moderate cytotoxicity against L1210 murine leukemia and KB human epidermoid carcinoma cells.


metachromin T

A sesquiterpenoid that is 6,8-dimethoxy-2,2-dimethyl-2H-chromen-5-ol in which the hydrogen of one of the methyl groups at position 2 is replaced by a [(1R,2S)-1,2,3-trimethylcyclohex-3-en-1-yl]methyl group. It is isolated from an Okinawan sponge Spongia sp.SS-1037 and shows moderate cytotoxicity against L1210 murine leukemia and KB human epidermoid carcinoma cells.


A member of the class of psoralens that is psoralen substituted by a methoxy group at position 4 and a [(2R)-3-butoxy-2-hydroxy-3-methylbutyl]oxy group at position 9. Isolated from the roots of Angelica dahurica, it exhibits inhibitory activity against COX-2 and 5-lipooxygenase.


A member of the class of isochromanes that is 3,4-dihydroisocoumarin substituted by an acetoxy group at position 4, a methoxy group at position 6 and a pentyl group at position 3. Isolated from Xyris pterygoblephara, it exhibits activity against dermatophyte fungi.


An indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines.


An indole alkaloid that is the 1-methoxy derivative of canthinone. Isolated from Ailanthus altissima and Leitneria floridana, it exhibits anti-HIV activity.


(+)-N-(methoxycarbonyl)-N-norboldine

An aporphine alkaloid that is laurolistine with a N-methoxycarbonyl group. Isolated from the aerial parts of Litsea cubeba, it exhibits antimicrobial activities.


A triterpene glycoside that consists of 25-O-methoxycimigenol attached to a alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. Isolated from the rhizomes of Cimicifuga racemosa, it exhibits cytotoxic activities.


A member of the class of 1,4-benzoquinones that is p-benzoquinone substituted by a methoxy group at position 2 and a 1-phenylallyl group at position 5. Isolated from the heartwood of Dalbergia louveli, it exhibits antiplasmodial activity.


An organic heterohexacyclic compound that is deoxymorellin substituted by a methoxy group at position 7. Isolated from Garcinia hanburyi, it exhibits cytotoxic activity.


4-methoxymagnaldehyde B

A lignan that consists of cinnamaldehyde substituted by a methoxy group at position 2 and a 4-allylphenolic group at position 5. Isolated from Magnolia obovata, it exhibits antineoplastic activity.


7-methoxypraecansone B

A member of the class of chalcones that is chalcone substituted by methoxy groups at positions 2', 6' and 7 and a dimethylpyrano ring substituted across positions 3' and 4'. Isolated from Pongamia pinnata, it has been found to induce quinone reductase.


SPIROTRYPROSTATIN B

An indole alkaloid isolated from a marine-derived fungal strain Aspergillus sydowii PFW1-13 and has been shown to exhibit cytotoxic activity.


methyl 3,5-di-O-caffeoyl quinate

A methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.


A benzoate ester that is methyl benzoate substituted by hydroxy groups at positions 3 and 4 and a prenyl group at position 5. Isolated from Piper glabratum and Piper acutifolium, it exhibits antileishmanial activity.


A benzoate ester that is methyl 4-aminobenzoate substituted by a 2,3-dihydroxy-3-methylbutyl group at position 2. It is isolated from the wood-decayed fungus Xylaria sp.BCC9653 and exhibits potent cytotoxicity against African green monkey kidney fibroblast (Vero) cells.


METHYLBREVIFOLIN CARBOXYLATE

An organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from  Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity.


A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 4 and 2', a prenyl group at position 3' and a beta-D-glucopyranosyloxy group at position 4'. Isolated from the stem barks of Maclura tinctoria, it exhibits antioxidant activity.


palau'amide

A 24-membered cyclodepsipeptide isolated from the cyanobacterium, Lyngbya sp. It exhibits strong cytotoxicity against KB human nasopharyngeal carcinoma cells.


pancixanthone B

A member of the class of xanthones that is a tetracyclic compound 1,2-dihydro-6H-furo[2,3-c]xanthen-6-one substituted by hydroxy groups at positions 5 and 10 and methyl groups at positions 1,1 and 2. It has been isolated from Calophyllum pauciflorum and Garcinia vieillardii.


BROUSSONOL E

A pentahydroxyflavone that is flavone substituted with hydroxy groups at positions 3, 5, 7, 3' and 4' and prenyl groups at positions 6 and 5'. Isolated from Broussonetia papyrifera, it exhibits inhibitory activity against phospholipase A2 and tyrosinase.


malvalic acid

A long-chain cyclopropenyl fatty acid comprising 8-heptadecenoic acid having a cyclopropene ring arising from the linking of C-8 and C-9 by a methylene substituent.


MALVIDIN

An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.


PF 1163A

A macrolide antibiotic that is 4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione substituted by a 4-(2-hydroxyethoxy)benzyl group at position 3 and a (2R)-2-hydroxypentyl group at position 13 (the 3S,10R,13S stereoisomer). It is isolated from Penicillium sp.PF1163 and exhibits antifungal activity against the  pathogenic fungal strain Candida albicans TIMM1768.


PF 1163B

A macrolide antibiotic that is 4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione substituted by a 4-(2-hydroxyethoxy)benzyl group at position 3 and a pentyl group at position 13 (the 3S,10R,13S stereoisomer). It is isolated from Penicillium sp.PF1163 and exhibits antifungal activity against the pathogenic fungal strain Candida albicans TIMM1768.


PHAKELLISTATIN 14

A homodetic cyclic peptide isolated from a marine sponge Phakellia sp. It exhibits cytotoxic activity against murine P388 lymphocytic leukemia cells and moderate cancer cell growth inhibitory activity against a panel of human cancer cells.


PHELLIGRIDIMER A

A  macrocycle isolated from the fungus Phellinus igniarius and has been shown to exhibit antioxidant activity.


PHELLIGRIDIN G

An organic heterotricyclic compound isolated from the fruiting bodies of the fungus Phellinus igniarius.


phomacin A

A cytochalasin isolated from a fungus Phoma sp. that has been shown to possess potent inhibitory activity against HT-29 colonic adenocarcinoma cells.


PHOMOXANTHONE A

A member of the class of  xanthones that is a dimer isolated from Phomopsis. It exhibits cytotoxic, antimalarial and antitubercular activities.


PHOMOXANTHONE B

A member of the class of xanthones that is a dimer isolated from Phomopsis. It exhibits cytotoxic, antimalarial and antitubercular activities.


phosphatoquinone A

An organic heterotricyclic compound resulting from the formal epoxidation of the 2-3 double bond of the 1,4-naphthoquinone moiety of phosphatoquinone B. It is isolated from the culture broth of Streptomyces sp.TC-0363 and exhibits inhibitory activity against the enzyme protein tyrosine phosphatase.


phosphatoquinone B

A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2, a methyl group at position 3, and hydroxy groups at positions 5 and 7. It is isolated from the culture broth of Streptomyces sp.TC-0363 and exhibits inhibitory activity against the enzyme protein tyrosine phosphatase.


PHOYUNBENE A

A  stilbenoid that is trans-stilbene substituted by hydroxy groups at positions 3 and 3' and methoxy groups at positions 2', 4' and 5. Isolated from Pholidota yunnanensis, it exhibits inhibitory effects on production of nitric oxide.


PHOYUNBENE B

A  stilbenoid that is trans-stilbene substituted by hydroxy groups at positions 3 and 4' and methoxy groups at positions 2', 3' and 5. Isolated from Pholidota yunnanensis, it exhibits inhibitory effects on production of nitric oxide.


PHOYUNBENE C

A  stilbenoid that is trans-stilbene substituted by hydroxy groups at positions 3 and 3' and methoxy groups at positions 2' and 5. Isolated from Pholidota yunnanensis, it exhibits inhibitory activity on nitric oxide production.


PHOYUNBENE D

A stilbenoid that is trans-stilbene substituted by a hydroxy group at position 3 and methoxy groups at positions 2', 3' and 5. Isolated from  Pholidota yunnanensis, it exhibits inhibitory effects on production of nitric oxide.


PLEOSPORONE

A carbotricyclic compound that is 1,2,3,4-tetrahydroanthracene-9,10-dione substituted by hydroxy groups at positions 1, 2, 3 and 8 and a methyl group at position 6. It is isolated from a pleosporalean ascomycete (MF7028), an endophytic fungus from Anthyllis vulneraria and exhibits modest antibacterial activity against a number of bacterial strains. Additionally it exhibits cytotoxicity against HeLa cells.


A a monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-[(1S)-1-amino-3-methylbutyl]-8-hydroxy-3,4-dihydro-1H-isochromen-1-one with the carboxy group of 4-amino-2,3-dihydroxy-6-methylheptanoic acid (the 2S,3S,4S stereoisomer). It is isolated from the culture broth of Bacillus sp.PhM-PHD-090 and exhibits potent antitumour activity.


polyketomycin

A carbohydrate-containing antibiotic isolated from the culture broth of Streptomyces sp.MK277-AF1. It exhibits potent antibacterial activity against several Gram-positive bacterial strains and is also found to be cytotoxic against a number of tumour cell lines.


PONCIRIN

A  flavanone glycoside that is  4'-methoxy-5,7-dihydroxyflavanone attached to a neohesperidose (alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose) residue via a glycosidic linkage. It has been isolated from the fruits of Poncirus trifoliata and exhibits inhibitory activity against liopolysaccharide (LPS)-induced prostaglandin E2 and interleukin-6 (IL-6) production.


A member of the class of  pyranoxanthones that is 3H,7H-pyrano[2,3-c]xanthen-7-one substituted by hydroxy groups at positions 6, 10 and 11, geminal methyl groups at position 3 and a prenyl group at position 5. Isolated from Garcinia lancilimba, it exhibits inhibitory effects on human cancer cell line.


A member of the class of  pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by hydroxy groups at positions 5, 8 and 9, geminal methyl groups at position 2 and a prenyl group at position 12. Isolated from Garcinia lancilimba, it exhibits inhibitory effects on human cancer cell line.


pyripyropene I

A  sesquiterpenoid that consists of a heterotetracyclic system linked to a pyridine moiety. Isolated from the fungus, Aspergillus fumigatus, it exhibits inhibitory activity against  acyl-CoA:cholesterol acyltransferase 2.


pyripyropene J

A sesquiterpenoid that consists of a heterotetracyclic system linked to a pyridine moiety. Isolated from the fungus, Aspergillus fumigatus, it exhibits inhibitory activity against acyl-CoA:cholesterol acyltransferase 2.


Oblonganoside A

A triterpenoid saponin thatr is the beta-D-glucopyranosyl ester of 3,23-O-hydroxyethylidene-3beta,23-dihydroxyurs-12,19(20)-dien-28-oic acid. Isolated from Ilex oblonga, it exhibits activity against TMV.


OBOCHALCOLACTONE

A member of the class of chalcones isolated from the trunk barks of Cryptocarya obovata and has been shown to exhibit cytotoxicity against the KB cell line.


OBOLACTONE

A pyranone isolated from the trunk barks of Cryptocarya obovata and has been shown to exhibit cytotoxicity against the KB cell line.


OBTUSAFURAN

A member of the class of 1-benzofurans that is 2,3-dihydro-1-benzofuran substituted by a hydroxy group at position 5, a methoxy group at position 6, a methyl group at position 3 and a phenyl group at position 2. Isolated from  Dalbergia louveli, it exhibits antiplasmodial activity.


OBYANAMIDE

A cyclodepsipeptide isolated from Lyngbya confervoides and has been shown to exhibit antineoplastic activity.


oceanalin A

A glycosphingolipid isolated from a marine sponge Oceanapia sp. that exhibits antifungal activity against fluconazole-resistant yeast Candida glabrata with an MIC value of 30 mug/ml.


ochracenomicin A

An angucycline antibiotic that is 3,4,4a,12b-tetrahydrotetraphene-1,7,12(2H)-trione substituted by hydroxy groups at positions 4a, 8 and 12b and a methyl group at position 3. It is isolated from the culture broth of Amycolatopsis sp.MJ950-89F4 and exhibits a broad spectrum of antibacterial potential.


OCHROCARPINONE A

A beta-diketone isolated from Ochrocarpos punctatus and has been shown to exhibit antineoplastic activity.


OCHROCARPIN A

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 2-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.


OCHROCARPIN B

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 3-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.


OCHROCARPIN C

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 2-methylpropanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.


OCHROCARPIN D

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-methoxypropan-2-yl group at position 8, a 2-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.


OCHROCARPIN E

A furanocoumarin that is 2,3-dihydro-7H-furo[2,3-f]chromen-7-one substituted by a hydroxy group at position 4, a 2-hydroxypropan-2-yl group at position 2, a 2-methylpropanoyl group at position 5 and a phenyl group at position 9. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.


A triterpenoid saponin that is the tetrasaccharide derivative of oleanolic acid. Isolated from the roots of Pulsatilla chinensis, it exhibits antineoplastic activity.


16-O-OLEOYL DANSHENXINKUN A

A diterpenoid with a fatty acyl side chain isolated from Salvia miltiorrhiza and has been shown to inhibit platelet aggregation induced by arachidonic acid.


MANGIFERIN

A C-glycosyl compound consisting of 1,3,6,7-tetrahydroxyxanthen-9-one having a beta-D-glucosyl residue at the 6-position.


onosmin A

An aminobenzoic acid that is anthranilic acid in which one of the hydrogens of the amino group is replaced by a 4-methylbenzyl group. Isolated from Onosma hispida, it exhibits inhibitory activity against lipoxygenase.


onosmin B

A benzoate ester obtained by the fromal condensation of the carboxy group of onosmin A with methanol. Isolated from Onosma hispida, it exhibits inhibitory activity against lipoxygenase.


OPHIOGLONIN

A homoflavonoid that is isochromeno[4,3-b]chromen-7(5H)-one substituted by hydroxy groups at positions 3, 4, 8 and 10. Isolated from Ophioglossum petiolatum, it exhibits anti-HBV activity.


ORBICULIN A

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by an acetoxy groups at positions 1 and 2 and benzoyloxy groups at positions 6 and 9 (the 1beta,2beta,6alpha,9alpha stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production.


orbiculin D

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by acetoxy group at position 1 and furoyloxy groups at positions 6 and 9 (the 1beta,6alpha,9alpha stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production.


orbiculin E

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by acetoxy group at positions 1 and 2, a benzoyloxy group at position 9 and furoyloxy groups at position 6 (the 1beta,2beta,9alpha,6alpha). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production.


orbiculin F

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by acetoxy group at position 1, benzoyloxy group at position 9 and furoyloxy groups at positions 2 and 6 (the 1beta,9alpha,2beta,6alpha stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production.


ORBICULIN G

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by an acetoxy group at position 1 and benzoyloxy groups at positions 2, 6 and 9 (the 1beta,2beta,6alpha,9alpha stereoisomers). Isolated from the roots of Celastrus orbiculatus and Microtropis fokienensis and exhibits cytotoxic and antitubercular properties.


orbiculin H

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by acetoxy groups at positions 1 and 8 and furoyloxy groups at positions 6 and 9 (the 1beta,8beta,6alpha,9alpha stereoisomer).  Isolated from Celastrus orbiculatus and exhibits inhibition of both NF-kappaB activation and nitric oxide production.


orbiculin I

A dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by an acetoxy group at position 1 and furoyloxy groups at positions 2, 6 and 9 (the 1beta,2beta,6alpha,9alpha stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production.


oriciacridone C

An alkaloid of the class of acridone derivatives that is 1,11-dihydrofuro[2,3-c]acridin-6(2H)-one substituted by hydroxy groups at positions 5 and 10 and a prop-1-en-2-yl group at position 2. Isolated from Oriciopsis glaberrima, it exhibits radical scavenging and alpha-glucosidase inhibitory activity.


oriciacridone F

An alkaloid of the class of acridone derivatives isolated from Oriciopsis glaberrima and has been shown to exhibit radical scavenging and alpha-glucosidase inhibitory activity.


oryzafuran

A member of the class of 1-benzofurans that is 1-benzofuran substituted by hydroxy groups at positions 4 and 6, a 3,4-dihydroxyphenyl group at position 2 and a methoxy carbonyl at position 3. Isolated from  black colored rice bran of Oryza sativa, it exhibits antioxidant activity.


A tetracyclic triterpenoid that is the 7-oxo derivative of cucurbitadienol. Isolated from Trichosanthes kirilowii, it exhibits anti-inflammatory activity.


7-oxo-3,8,9-trihydroxy staurosporine

A indolocarbazole alkaloid that is staurosporine substituted by hydroxy groups at positions 3, 8 and 9 and an oxo group at position 7. Isolated from Cystodytes solitus, it exhibits cytotoxic activity.


A indolocarbazole alkaloid that is 4'-N-demethyl staurosporine substituted by hydroxy groups at positions 8 and 9 and an xo group at position 7. Isolated from Cystodytes solitus, it exhibits antineoplastic activity.


An oxoaporphine alkaloid that is 7H-dibenzo[de,g]quinolin-7-one substituted by a methylenedioxy group across positions 1 and 2, a methoxy group at position 11 and a hydroxy group at position 10. Isolated from Hernandia nymphaeifolia and Lindera chunii, it exhibits activity against HIV-1 integrase.


18-OXOTRYPROSTATIN A

An indole alkaloid that is tryprostatin A substituted by an oxo substituent at position 18. Isolated from Aspergillus sydowii, it exhibits cytotoxicity.


oxypeucedanin hydrate acetonide

A furanocoumarin that is 7H-furo[3,2-g]chromen-7-one substituted by a (2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methoxy moiety at position 4. Isolated from  Peucedanum turcomanicum and Angelica dahurica, it exhibits cytotoxic activity.


phosphatidylcholine 32:6

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 6 double bonds.


phosphatidylcholine 32:5

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 5 double bonds.


phosphatidylcholine 32:4

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 4 double bonds.


phosphatidylcholine 32:3

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 3 double bonds.


phosphatidylcholine 32:2

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 2 double bonds.


phosphatidylcholine 32:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 1 double bond.


phosphatidylcholine 32:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 32 carbons in total with 0 double bonds.


phosphatidylcholine 34:6

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 34 carbons in total with 6 double bonds.


phosphatidylcholine 34:5

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 34 carbons in total with 5 double bonds.


phosphatidylcholine 34:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 34 carbons in total with 0 double bonds.


phosphatidylcholine 36:6

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 36 carbons in total with 6 double bonds.


phosphatidylcholine 36:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 36 carbons in total with 1 double bond.


phosphatidylcholine 36:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 36 carbons in total and 0 double bonds.


phosphatidylcholine 38:2

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 38 carbons in total with 2 double bonds.


phosphatidylcholine 38:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 38 carbons in total with 1 double bond.


phosphatidylcholine 38:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 38 carbons in total with 0 double bonds.


phosphatidylcholine 40:4

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 40 carbons in total and 4 double bonds.


phosphatidylcholine 40:3

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 40 carbons in total with 3 double bonds.


phosphatidylcholine 40:2

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 40 carbons in total with 2 double bonds.


phosphatidylcholine 40:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 40 carbons in total with 1 double bond.


phosphatidylcholine 40:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 40 carbons in total with 0 double bonds.


trans,polycis-decaprenyl phosphate

A polyprenol phosphate having ten prenyl units in the chain (the 2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E-isomer)


carboxyspermidine

An L-alpha-amino acid that is spermidine (1,5,10-triazadecane) carboxylated with S-configuration at the 2-position.


C4-dicarboxylic acid

Any dicarboxylic acid that contains four carbon atoms.


carnosinate

An N-acyl-L-alpha-amino acid anion that is the conjugate base of carnosine, obtained by deprotonation of the carboxy group.


A branched amino trisaccharide consisting of D-galactose having an alpha-L-fucosyl residue at the 2-position and an alpha-D-galactosaminyl residue at the 3-position.


avanafil

A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid with the amino group of pyrimidin-2-ylmethylamine. Used for treatment of erectile dysfunction.


A linear trisaccharide comprised of mannose, rhamnose and galactose residues linked alpha(1->4) and alpha(1->3), respectively, with alpha configuration at the anomeric centre of the galactose residue.


An organic cation that is the conjugate acid of pseudooxynicotine, obtained by protonation of the secondary amino group; major species at pH 7.3.


A member of the class of butanals that is succinic semialdehyde in which the hydroxy group of the carboxylic acid function is replaced by a pyridin-3-yl group.


florbetapir

An aromatic ether consisting of a pyridine ring substituted at position 2 by a 2-{2-[2-((18)F)fluoroethoxy]ethoxy}ethoxy group and at position 5 and a 2-(4-methylaminophenyl)vinyl group. A positron emission tomography imaging ligand for the detection of amyloid aggregation associated with Alzheimer disease.


An organophosphate oxoanion obtained by deprotonation of the phosphate OH group of trans,octacis-decaprenylphospho-beta-D-ribofuranose; major species at pH 7.3.


4-(methylamino)butyric acid zwitterion

An amino acid zwitterion resulting from the transfer of a proton from the carboxy group to the amino group of 4-(methylamino)butyric acid.


A linear tetrasaccharide comprised of tyvelose, mannose, rhamnose and galactose residues linked alpha(1->3, alpha(1->4) and alpha(1->3), respectively, with alpha configuration at the anomeric centre of the galactose residue.


N-alkylglycine zwitterion

An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of any N-alkylglycine; major species at pH 7.3.


An oligosaccharide of 12 residues, comprising three (1->3)-linked alpha-D-Gal-(1->2)-[alpha-Tyv-(1->3)]-alpha-D-Man-(1->4)-alpha-L-Rha units.


A 2-hydroxy-6-oxonona-2,4-dienedioate having (2Z,4E)-configuration.


A 2-hydroxy-6-oxonona-2,4,7-trienedioate having (2Z,4E,7E)-configuration.


A tetrasaccharide comprising paratose, D-mannose, L-rhamnose and D-galactose residues linked alpha(1->3), alpha(1->4) and alpha(1->3) respectively.


A C-nitro compound in which the nitro compound is meta to the amino group and para to the methyl group of o-toluidine.


O-TOLYLAMINE

An aminotoluene in which the amino substituent is ortho to the methyl group.


A 4-oxo monocarboxylic acid anion that is the conjugate base of 4-(6-hydroxypyridin-3-yl)-4-oxobutyric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


peginesatide acetate

An acetate salt obtained by reaction of peginesatide with two equivalents of acetic acid. Used for the treatment of anemia due to chronic kindney disease in patients on dialysis.


An optically active 5-oxo-1,2-campholide having (+)-(1S,5S)-configuration.


A cyclic peptide cation obtained by protonation of the arginine side-chains of peginesatide.


A retinal that is 11-cis-retinal substituted at position 3 on the cyclohexenyl ring by a hydroxy group (the R-enantiomer).


tafluprost

A prostaglandin Falpha that is prostaglandin F2alpha in which the carboxylic acid function has been converted to the corresponding isopropyl ester and the 3-hydroxy-1-octenyl side-chain is substituted by 3,3-difluoro-4-phenoxybut-1-enyl. Used for treatment of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.


PHENYL ETHANOL

An aromatic alcohol that is ethanol substituted by a phenyl group at position 1.


ivacaftor

An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.


vismodegib

A benzamide obtained by formal condensation between the carboxy group of 2-chloro-4-(methylsulfonyl)benzoic acid and the anilino group of 4-chloro-3-(pyridin-2-yl)aniline. Used for the treatment metastatic basal cell carcinoma.


A beta-D-glucoside in which a beta-D-glucopyranosyl residue is attached at position 4' of 2',3,4,4',6'-pentahydroxychalcone via a glycosidic linkage.


aureusidin 6-O-beta-glucoside

A beta-D-glucoside in which a beta-D-glucopyranosyl residue is attached at position 6 of aureusidin via a glycosidic linkage.


A beta-D-glucoside in which a beta-D-glucopyranosyl residue is attached at position 4' of 2',4,4',6'-tetrahydroxychalcone via a glycosidic linkage.


bracteatin 6-O-beta-glucoside

A beta-D-glucoside in which a beta-D-glucopyranosyl residue is attached at position 6 of bracteatin via a glycosidic linkage.


A glycosylrhamnose consisting of L-rhamnose having an alpha-D-glucosyl residue attached at the 3-position.


axitinib

An indazole substituted at position 3 by a 2-(pyridin-2-yl)vinyl group and at position 6 by a 2-(N-methylaminocarboxy)phenylsulfanyl group. Used for the treatment of advanced renal cell carcinoma after failure of a first line systemic treatment.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of alpha-D-mannosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-beta-D-galactosyl-1-diphosphodecaprenol.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of alpha-D-abequosyl-(1->3)-alpha-D-mannosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-beta-D-galactosyl-1-diphosphodecaprenol.


ingenol mebutate

A tetracyclic diterpenoid ester obtained by formal condensation of the carboxy group of (2Z)-2-methylbut-2-enoic (angelic) acid with the 3-hydroxy group of ingenol. Used for the topical treatment of actinic keratosis.


A UDP-D-galactose(2-) in which the anomeric centre of the galactose moiety has alpha-configuration.


A UDP-D-galactofuranose(2-) in which the anomeric centre of the galactofuranose moiety has alpha-configuration.


alanine zwitterion

An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of alanine; major species at pH 7.3.


A phytosterol consiting of ergostane having double bonds at the 5,6- and 7,8-positions as well as a 3beta-hydroxy group.


ruxolitinib

A pyrazole substituted at position 1 by a 2-cyano-1-cyclopentylethyl group and at position 3 by a pyrrolo[2,3-d]pyrimidin-4-yl group. Used as the phosphate salt for the treatment of patients with intermediate or high-risk myelofibrosis, including primary myelofibrosis, post-polycythemia vera myelofibrosis and post-essential thrombocythemia myelofibrosis.


A C-nitro compound in which the nitro compound is ortho to the amino group and meta to the methyl group of p-toluidine.


citrullinate

An alpha-amino acid anion that is the conjugate base of citrulline, obtained by deprotonation of the carboxy group.


(2-nitrophenoxy)acetic acid

A monocarboxylic acid comprising acetic acid substituted at the alpha carbon with a 2-nitrophenoxy group.


creatinate

A monocarboxylic acid anion that is the conjugate base of creatine, obtained by deprotonation of the carboxy group.


2-amino-5-nitrobenzenesulfonic acid

The arenesulfonic acid that is benzenesulfonic acid substituted at the ortho position by an amino group and at the para posiion


A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.


Benzaldehyde substituted at the ortho-position with a nitro group.


A C-nitro compound in which the nitro group is substituted into the 4-position of benzohydrazide.


A polyprenyl glycosyl phosphate consisting of beta-D-ribose attached at the 1-position to trans,octacis-decaprenyl phosphate.


An azobenzene in which the phenyl rings are 4-nitro- and 2,4-dihydroxy-substituted respectively.


A member of the class of phenylhydrazines that is  phenylhydrazine substituted at the 4-position by a nitro group.


A  C-nitro compound that is phenylhydrazine substituted at the 2- and 4-positions by nitro groups.


N-alkylglycine

Any glycine derivative in which glycine is substituted at position 2 by an alkyl group.


cyanoamino acid anion

An amino acid anion modified by the addition of a cyano group.


A 2-hydroxy-6-oxonona-2,4-dienedioic acid having (2Z,4E)-configuration.


Needed for the new reaction: trans,octacis-decaprenyl phosphate + 5-phospho-alpha-D-ribose 1-diphosphate = trans,octacis-decaprenylphospho-beta-D-ribofuranose 5-phosphate + diphosphate


keto-D-gluconic acid

A ketogluconic acid of D-configuration.


A 2-hydroxy-6-oxonona-2,4,7-trienedioic acid having (2Z,4E,7E)-configuration.


maritimetin

A hydroxyaurone that is aurone substituted by hydroxy groups at positions 6, 7, 3' and 4' respectively.


fructosylglycinate

A glyco-amino-acid anion formed by loss of a proton from the carboxy group of fructosylglycine.


ecgononium methyl ester(1+)

An organic cation that is the conjugate acid of ecgonone methyl ester arising from protonation of the tertiary amino group; major species at pH 7.3.


A carboxylic acid anion resulting from the removal of a proton from the carboxy group of 4-oxo-4-(pyridin-3-yl)butanoic acid. The major species at pH 7.3.


A 2-hydroxy-6-oxohexa-2,4-dienoate having (2E,4Z)-configuration.


An organic cation that is the conjugate acid of 2,6-dihydroxypseudooxynicotine, obtained by protonation of the secondary amino group; major species at pH 7.3.


A dicarboxylic acid dianion obtained by deprotonation of the carboxy groups of 4-nitro-6-oxohepta-2,4-dienedioic acid; major species at pH 7.3.


A 4-oxo monocarboxylic acid that is succinic acid in which one of the carboxyl hydroxy groups is substituted by a 6-hydroxypyridin-3-yl group.


A 6-oxo monocarboxylic acid anion that is the conjugate base of (2E,4Z)-4-hydroxy-6-oxohexa-2,4-dienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A beta-amino-acid anion that is the conjugate base of isoglutamic acid, obtained by deprotonation of the carboxy groups and protonation of the amino group; major species at pH 7.3.


nucleoside 3'-phosphate(2-)

An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of any nucleoside 3'-phosphate.


olivetolate

A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of olivetolic acid. The major species at pH 7.3.


4-oxo-4-(pyridin-3-yl)butanoic acid

A monocarboxylic acid that is succinic acid in which the hydroxy group of one of the carboxy groups is replaced by a pyridin-3-yl group.  A byproduct of tobacco-specific N-nitrosamines generated by cytochrome P-450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation, this nicotine metabolite is commonly found in the urine of smokers.


homocysteinate

An alpha-amino acid anion that is the conjugate base of homocysteine, obtained by deprotonation of the carboxy group.


A bridged compound that is 1,2-campholide substituted at position 5 by an oxo group.


2',3'-cyclic nucleotide(1-)

An organophosphate oxoanion obtained by deprotonation of the phosphate OH group of any 2',3'-cyclic nucleotide.


olivetolic acid

A member of the class of benzoic acids that is salicylic acid in which the hydrogens ortho- and para- to the carboxy group are replaced by a pentyl and a hydroxy group, respectively.


An acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of 3,5,7-trioxododecanoyl-CoA; major species at pH 7.3.


A pyranone that is 2H-pyran-2-one in which the hydrogens at positions 4 and 6 are substituted by hydroxy and pentyl groups respectively.


A pyranone that is 2H-pyran-2-one in which the hydrogens at positions 4 and 6 are substituted by hydroxy and 2-oxoheptyl groups respectively.


WHILE OLIVETOL

A member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group.


cannabinerolate

A dihydroxybenzoate that is the conjugate base of cannabinerolic acid, obtained by deprotonation of the carboxy group.


cannabigerolate

A dihydroxybenzoate that is the conjugate base of cannabigerolic acid, obtained by deprotonation of the carboxy group.


A hydroxy monocarboxylic acid anion that is the conjugate base of Delta(9)-tetrahydrocannabinolic acid, obtained by deprotonation of the carboxy group.


A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.


phosphatidylcholine 42:6

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 6 double bonds.


phosphatidylcholine 42:5

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 5 double bonds.


phosphatidylcholine 42:4

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 4 double bonds.


phosphatidylcholine 42:3

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 3 double bonds.


phosphatidylcholine 42:2

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 2 double bonds.


phosphatidylcholine 42:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 1 double bond.


phosphatidylcholine 42:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 0 double bonds.


A sialopentaosylceramide having beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-GalNAc-(1->3)-beta-D-Gal-(1->4)-beta-D-Glc as the sialopentaosyl component.


phosphatidylcholine 44:6

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 6 double bonds.


phosphatidylcholine 44:5

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 5 double bonds.


phosphatidylcholine 44:4

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 4 double bonds.


phosphatidylcholine 44:3

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 3 double bonds.


phosphatidylcholine 44:2

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 2 double bonds.


phosphatidylcholine 44:1

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 1 double bond.


phosphatidylcholine 44:0

A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at C-1 and C-2 contain 44 carbons in total with 0 double bonds.


MATAIRESINOL

A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).


nootropic agent

Any compound that improves mental functions such as cognition, memory, intelligence, motivation, attention, and concentration.


A carbohydrate acid derivative anion that is the conjugate base of mycophenolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A ceramide that is the N-2-hydroxydocosanoyl derivative of eicosasphinganine.


N-(docosanoyl)eicosasphinganine

A ceramide that is the N-docosanoyl derivative of eicosasphinganine.


A ceramide that is the N-docosanoyl derivative of 4-hydroxyeicosasphinganine.


A ceramide that is the N-(2-hydroxydocosanoyl) derivative of 4-hydroxyeicosasphinganine.


N-(tetracosanoyl)eicosasphinganine

A ceramide that is the N-tetracosanoyl derivative of eicosasphinganine.


A ceramide that is the N-(2-hydroxytetracosanoyl) derivative of eicosasphinganine.


A ceramide that is the N-tetracosanoyl derivative of 4-hydroxyeicosasphinganine.


A ceramide that is the N-(2-hydroxytetracosanoyl) derivative of 4-hydroxyeicosasphinganine.


N-hexacosanoylicosasphinganine

A C20 dihydroceramide in which the ceramide N-acyl group is specified as hexacosanoyl.


A ceramide that is the N-(2-hydroxyhexacosanoyl) derivative of eicosasphinganine.


A ceramide that is the N-(2-hydroxyhexacosanoyl) derivative of 4-hydroxyeicosasphinganine.


N-(eicosanoyl)eicosasphinganine

A ceramide that is the N-eicosanoyl derivative of eicosasphinganine.


histidinate derivative

A carboxylic acid anion which is a conjugate base of  a histidine derivative  having either D- or L-configuration.


A ceramide that is the N-(2-hydroxyeicosanoyl) derivative of eicosasphinganine.


A phenylethylamine that is ethylamine substituted by a phenyl group at position 1.


A ceramide that is the N-eicosanoyl derivative of 4-hydroxyeicosasphinganine.


hypusinate

A L-alpha-amino acid anion obtained by the deprotonation of the carboxy group of hypusine.


A branched amino trisaccharide that consists of N-acetyl-alpha-D-galactosamine having a beta-D-galactosyl residue attached at the 3-position and a beta-N-acetylneuraminosyl residue attached at the 6-position.


A ceramide that is the N-(2-hydroxyeicosanoyl) derivative of 4-hydroxyeicosasphinganine.


N-(octadecanoyl)eicosasphinganine

A ceramide that is the N-stearoyl (octadecanoyl) derivative of eicosasphinganine.


A ceramide that is the N-(2-hydroxyoctadecanoyl) derivative of eicosasphinganine.


A ceramide that is the N-stearoyl (octadecanoyl) derivative of 4-hydroxyeicosasphinganine.


A ceramide that is the N-(2-hydroxyoctadecanoyl) derivative of 4-hydroxyeicosasphinganine.


kynureninate

An alpha-amino-acid anion obtained by the deprotonation of the carboxy group of kynurenine.


S-adenosyl-L-homocysteinate

A L-alpha-amino acid anion obtained by deprotonation of S-adenosyl-L-homocysteine.


MAYTANSINE

An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.


L-kynureninate

A L-alpha-amino acid anion obtained by the deprotonation of the carboxy group of L-kynurenine .


folates

An N-acyl-L-alpha-amino acid anion obtained by deprotonation of any folic acid.


A L-alpha-amino acid anion which is the conjugate base of L-dopa, obtained by deprotonation of the carboxy group: major species at pH 7.3.


methyl-branched fatty acid anion

Any branched-chain fatty acid anion containing methyl branches only.


dihydrofolates

A folate obtained by deprotonation of any dihydrofolic acid.


N(omega)-methyl-L-argininate

A L-alpha-amino acid anion obtained by deprotonation of the carboxy group of N(omega)-methyl-L-arginine.


tetrahydrofolate

A folate obtained by deprotonation of any tetrahydrofolic acid.


N-(hexadecanoyl)eicosasphinganine

A ceramide that is the N-palmitoyl (hexadecanoyl) derivative of eicosasphinganine.


A ceramide that is the N-(2-hydroxyhexadecanoyl) derivative of eicosasphinganine.


A ceramide that is the N-palmitoyl (hexadecanoyl) derivative of 4-hydroxyeicosasphinganine.


A ceramide that is the N-(2-hydroxyhexadecanoyl) derivative of 4-hydroxyeicosasphinganine.


N-docosanoylsphinganine

A dihydroceramide in which the ceramide N-acyl group is specified as docosanoyl (behenoyl).


lipoxin anion

An unsaturated fatty acid anion obtained by the deprotonation of the carboxy group of any lipoxin.


A dihydroceramide in which the ceramide N-acyl group is specified as 2-hydroxydocosanoyl.


A phytoceramide in which the ceramide N-acyl group is specified as docosanoyl (behenoyl).


A phytoceramide in which the ceramide N-acyl group is specified as 2-hydroxydocosanoyl.


lipoxin A4(1-)

A hydroxy fatty acid anion obtained by deprotonation of the carboxy function of lipoxin A4: major species at pH 7.3.


N-eicosanoylsphinganine

A dihydroceramide in which the ceramide N-acyl group is specified as eicosanoyl


A dihydroceramide in which the ceramide N-acyl group is specified as 2-hydroxyeicosanoyl.


A phytoceramide in which the ceramide N-acyl group is specified as eicosanoyl.


A phytoceramide in which the ceramide N-acyl group is specified as 2-hydroxyeicosanoyl.


lipoxin B4(1-)

A hydroxy fatty acid anion obtained by the deprotonation of the carboxy group of lipoxin B4: major species at pH 7.3.


An organophosphate oxoanion that is the dianionic form of O-phosphoserine having anionic phosphate and carboxy functions and a protonated amino group.


N-octodecanoylsphinganine

A dihydroceramide in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl).


A dihydroceramide in which the ceramide N-acyl group is specified as 2-hydroxyoctadecanoyl.


A phytoceramide in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl).


An organophosphate oxoanion obtained by the deprotonation of the carboxy and phospho groups and protonation of the amino group of O-(N-acetylglucosamine-1-phosphoryl)-L-serine: major species at pH 7.3.


An D-alpha-amino acid anion  arising from deprotonation of the carboxy groups and protonation of the guanidino group of D-octopine.


prenylcysteinate

A sulfur-containing amino-acid anion which is a conjugate base of prenylcysteine.


mebendazole

A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.


A phytoceramide in which the ceramide N-acyl group is specified as 2-hydroxyoctadecanoyl


N-hexadecanoylsphinganine

A dihydroceramide in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl).


A dihydroceramide in which the ceramide N-acyl group is specified as 2-hydroxyhexadecanoyl


A phytoceramide in which the ceramide N-acyl group is specified as 2-hydroxyhexadecanoyl


N-tetradecanoylsphinganine

A dihydroceramide in which the ceramide N-acyl group is specified as tetradecanoyl (myristoyl).


A dihydroceramide in which the ceramide N-acyl group is specified as 2-hydroxytetradecanoyl.


A phytoceramide in which the ceramide N-acyl group is specified as tetradecanoyl (myristoyl).


A phytoceramide in which the ceramide N-acyl group is specified as 2-hydroxytetradecanoyl.


A quaternary ammonium ion obtained by the protonation of the carboxy function of N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine.


S-methyl-L-methioninate

A sulfonium betaine that is a conjugate base of S-methyl-L-methionine obtained by the deprotonation of the carboxy group.


phosphopantetheine anion

An organophosphate oxoanion obtained by deprotonation of one or more phosphate OH groups of any phosphopantetheine.


An organophosphate oxoanion obtained by the deprotonation of the carboxy and one of the phosphate OH groups of glyphosate.


lysophosphatidylcholine 14:2

A lysophosphatidylcholine in which the remaining acyl group contains 14 carbons and 2 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 14:1

A lysophosphatidylcholine in which the remaining acyl group contains 14 carbons and 1 double bond. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 16:2

A lysophosphatidylcholine in which the remaining acyl group contains 16 carbons and 2 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 20:2

A lysophosphatidylcholine in which the remaining acyl group contains 20 carbons and 2 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 20:1

A lysophosphatidylcholine in which the remaining acyl group contains 20 carbons and 1 double bond. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 20:0

A lysophosphatidylcholine in which the remaining acyl group contains 20 carbons and 0 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 22:2

A lysophosphatidylcholine in which the remaining acyl group contains 22 carbons and 2 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 22:1

A lysophosphatidylcholine in which the remaining acyl group contains 22 carbons and 1 double bond. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lysophosphatidylcholine 22:0

A lysophosphatidylcholine in which the remaining acyl group contains 22 carbons and 0 double bonds. If R1 is the acyl group and R2 is a hydrogen then the molecule is a 1-acyl-sn-glycero-3-phosphocholine. If R1 is a hydrogen and R2 is the acyl group then the molecule is a 2-acyl-sn-glycero-3-phosphocholine.


lipo-chitin oligosaccharide

Glycolipid signal molecules that mediate the species-specific symbiosis between rhizobial bacteria and leguminous plants. Comprised of an oligosaccharide backbone of beta (1-4) linked N-acetyl-D-glucosamine (GlcNAc) which varies in length between two and six residues and which is decorated with a combination of chemical moieties that helps encode species-specificity.


A cell surface polysaccharide expressed by a variety of Gram-positive and Gram-negative bacterial pathogens, including Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Acinetobacter baumannii, and others.


phosphatidylcholine O-36:4

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 36 carbons and 4 double bonds.


phosphatidylcholine O-36:2

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 36 carbons and 2 double bonds.


phosphatidylcholine O-36:1

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 36 carbons and 1 double bond.


phosphatidylcholine O-36:0

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 36 carbons and 0 double bonds.


phosphatidylcholine O-38:3

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 38 carbons and 3 double bonds.


phosphatidylcholine O-38:2

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 38 carbons and 2 double bonds.


phosphatidylcholine O-38:1

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 38 carbons and 1 double bond.


phosphatidylcholine O-38:0

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 38 carbons and 0 double bonds.


cannabinoid receptor agonist

An agonist that binds to and activates cannabinoid receptors.


phosphatidylcholine O-34:6

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 6 double bonds.


phosphatidylcholine O-34:5

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 5 double bonds.


phosphatidylcholine O-34:4

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 4 double bonds.


phosphatidylcholine O-34:1

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 1 double bond.


phosphatidylcholine O-34:0

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 0 double bonds.


Δ9-Tetrahydrocannabinolic acid

A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.


anti-inflammatory agent

Any compound that has anti-inflammatory effects.


cannabinerolic acid

A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a neryl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.


CANNABIGEROLIC ACID

A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.


phosphatidylcholine O-44:6

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 6 double bonds.


phosphatidylcholine O-44:5

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 5 double bonds.


phosphatidylcholine O-44:4

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 4 double bonds.


phosphatidylcholine O-44:3

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 3 double bonds.


phosphatidylcholine O-44:2

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 2 double bonds.


phosphatidylcholine O-44:1

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 1 double bond.


phosphatidylcholine O-44:0

A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 44 carbons and 0 double bonds.


An oxo fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3,5,7-trioxododecanoic acid.


A sphingomyelin having sphinganine as the sphingoid component.


A sphingomyelin in which the sphingoid component is specified as C17-sphinganine.


A sphingomyelin in which the sphingoid component is specified as 4-hydroxyheptadecasphinganine.


A sphingomyelin in which the sphingoid component is specified as C17-sphingosine.


A branched amino tetrasaccharide that consists of the linear trisaccharide alpha-L-fucosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)-N-acetyl-D-glucosamine in which an alpha-L-fucosyl residue is attached at position 3 of the glucoamine.


A triol comprising heptane substituted with hydroxy groups at C-1, -2 and -3.


decyl beta-D-maltopyranoside

A glycoside resulting from attachment of a decyl group to the reducing-end anomeric centre of a beta-maltose molecule.


meclofenamic acid

An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoea (painful periods), osteoarthritis and rheumatoid arthritis.


pentaerythritol propoxylate (5/4 PO/OH)

A hydroxypolyether in which a hydroxy-poly(propylene oxide) chain is connected to each of the methyl groups of neopentane. It is commonly used to crystallise proteins. In the diagram, a + b + c + d ~ 5.


A linear amino trisaccharide consisting of alpha-L-fucose,N-acetyl-beta-D-galactosamine and N-acetyl-D-glucosamine residues joined in sequence by (1->3)- and (1->4)-linkages respectively.


A muconic semialdehyde that is hexa-2,4-dienoic acid substituted at positions 4 and 6 by hydroxy and oxo groups respectively (the 2E,4Z-isomer).


4-nitro-6-oxohepta-2,4-dienedioic acid

An oxo dicarboxylic acid that is 6-oxohepta-2,4-dienedioic acid substituted at position 4 by a nitro group.


A bioactive sphingoid, sphinganine, in which the terminal hydroxy group has been replaced by a hydrogen.


dimethylmyleran

A methanesulfonate ester that is hexane-2,5-diol in which the hydrogens of the hydroxy groups are replaced by methanesulfonyl groups.


A cationic sphingoid obtained by the protonation of the amino group of 1-deoxymethylsphinganine.


A cationic sphingoid obtained by protonation of the amino group of 1-deoxysphinganine; major species at pH 7.3.


A 2-hydroxy-6-oxohexa-2,4-dienoic acid having (2E,4Z)-configuration.


A ceramide which consists of 1-deoxysphinganine in which one of the hydrogens of the amino group is substituteby a fatty acyl group.


A ceramide  that consists of 1-deoxy-4-hydroxysphinganine in which one of the hydrogens of the amino group is substituted by a fatty acyl group.


CHLORANTRANILIPROLE

A carboxamide resulting from the formal condensation of the carboxylic acid group of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid with the primary amino group of 2-amino-5-chloro-N,3-dimethylbenzamide. The first of the anthranilic diamide insecticides, it is a ryanodine receptor activator and is used to protect a wide variety of crops, including corn, cotton, grapes, rice and potatoes.


ecgonone methyl ester

The methyl ester of (1R,2R,5S)-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylic acid (ecgonone).


The primary amino compound that is 1,2-phenylenediamine (o-phenylenediamine) substituted at the 4- (para-) position by a nitro group.


A polyprenyl glycosyl phosphate consisting of beta-D-ribose-5-phosphate attached at the 1-position to trans,octacis-decaprenyl phosphate via a glycosyl phosphate linkage.


UDP-alpha-D-galactofuranose

A UDP-D-galactofuranose in which the anomeric centre of the galactofuranose moiety has alpha-configuration.


UDP-galactose

A UDP-D-galactose in which the anomeric centre of the galactose moiety has alpha-configuration.


4-nitrotoluene-2-sulfonic acid

The arenesulfonic acid that is toluene-2-sulfonic acid bearing a nitro substituent at C-4.


nitroxoline

A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.


A polyprenyl glycosyl phosphate consisting of alpha-D-abequosyl-(1->3)-alpha-D-mannosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-beta-D-galactose attached at the 1-position to decaprenyl phosphate.


A C-nitro compound that is nitrobenzene bearing an iodine substituent at C-3.


A polyprenyl glycosyl phosphate consisting of alpha-D-mannosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-beta-D-galactose attached at the 1-position to decaprenyl phosphate.


A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the 'popcorn' aroma in a large variety of cereal and food products. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions.


Biphenyl substituted with nitro groups at the 2- and 2'-positions.


A naphthol in which the hydroxy substituent is at C-1 with nitro groups at C-2 and -4.


PHENETOLE

An aromatic ether in which the ether oxygen is bonded to an ethyl and a phenyl group.


An aromatic ether comprised of phenetole substituted at C-2 and C-4 by nitro groups.


ditrans,polycis-polyprenol

A polyprenol in which all linkages of the isoprene units are cis, except for the two furthest from the hydroxy group which are trans.


A nucleotide-sugar oxoanion arising from deprotonation of the diphosphate OH groups of UDP-4-amino-4,6-dideoxy-N-acetyl-alpha-D-glucosamine.


A nucleotide-sugar oxoanion that is the conjugate base of UDP-N,N'-diacetylbacillosamine, having an anionic diphosphate function; major microspecies present at pH 7.3.


AZOMYCIN

An imidazole that is 1H-imidazole substituted at position 2 by a nitro group.


cannabidiolate

A dihydroxybenzoate that is the conjugate base of cannabidiolic acid, obtained by deprotonation of the carboxy group.


A UDP-N-acetyl-D-galactosamine(2-) in which the anomeric centre of the galactosamine moiety has alpha-configuration; major species at pH 7.3.


The dicarboxylic acid dianion formed from (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid by proton loss from both carboxy groups; major species present at pH 7.3.


(+)-medicarpin

The (+)-enantiomer of medicarpin.


phosphate monoester dianion

Any organphosphate oxoanion resulting from the removal of both protons from the phosphate group of a phosphate monoester. The major species at pH 7.3.


An ammonium ion resulting from the protonation of the tertiary amino group of lycanthone.


nucleobase analogue

A molecule that can substitute for a normal nucleobase in nucleic acids.


An oligonucleotide comprised of three adenosine residues linked 2'->5' and with a triphosphate group at the 5' terminus.


A primary alcohol that is ethanol in which one of the methyl hydrogens is replaced by a morpholin-4-yl group.


fumigaclavine A(1+)

An ammonium ion obtained by the protonation of the tertiary amino group of fumigaclavine A; major species at pH 7.3.


fumigaclavine B(1+)

An ammonium ion obtained by the protonation of the tertiary amino group of the fumigaclavine B; major species pH 7.3.


fumigaclavine C(1+)

An ammonium ion obtained by the protonation of the tertiary amino group of fumigaclavine C; major species at pH 7.3.


An acyl-CoA(4-) that is the tetraanion of 2-hydroxybenzoyl-CoA, arising from deprotonation of phosphate and diphosphate functions; major species at pH 7.3.


A glycosylglycerol derivative in which the glycosyl moiety is alpha-D-glucosyl attached at O-3, with O-1 and O-2 both acylated.


medroxyprogesterone

A 3-oxo Delta(4)-steroid that is pregn-4-ene-3,20-dione substituted by an alpha-hydroxy group at position 17 and a methyl group at position 6.


A glycosylglycerol derivative in which the glycosyl moiety is beta-D-glucosyl attached at O-3, with O-1 and O-2 both acylated.


A 2-hydroxypenta-2,4-dienoate in which the double bond between positions 2 and 3 has Z- (trans-) geometry.


(+)-larreatricin

An antiviral lignan isolated from the creosote bush, Larrea tridentata, which consists of a 3,4-dimethyltetrahydrofuran skeleton substituted by 4-hydroxyphenyl groups at positions 2 and 5 (the 2R,3R,4S,5R stereoisomer).


An antiviral lignan isolated from Larrea tridentata, which consists of a 3,4-dimethyltetrahydrofuran skeleton substituted by a dihydroxybenzyl and hydroxyphenyl groups at position 2 and 5 respectively (the 2R,3S,4R,5R stereoisomer).


fumigaclavine B

An ergot alkaloid produced by the fungus Aspergillus fumigatus that consists of ergoline substituted by two methyl groups at the 6 and 8beta positions, and by a hydroxy group at the 9beta position.


An amino oligosaccharide comprising 4 fucose, 2 galactose, 4 N-acetyl glucosamine and 3 mannose residues arranged as two alpha-L-Fuc-(1->2)-beta-D-Gal-(1->4)-[alpha-L-Fuc-(1->3)]-beta-D-GlcNAc-(1->2)-alpha-D-Man brached chains linked (1->3) and (1->6)to a beta-D-Man-(1->4)-beta-D-GlcNAc-(1->4)-D-GlcNAc trisaccaride chain.


An optically active form of 3-ammonio-3-phenylpropanoate having (R)-configuration.


fumigaclavine A

An ergot alkaloid produced by the fungus Aspergillus fumigatus that is ergoline which is substituted by methyl groups at the 6 and 8beta positions, and by an acetoxy group at the 9beta position.


medroxyprogesterone

An acetate ester resulting from the formal condensation of the 17alpha-hydroxy group of medroxyprogesterone with the carboxy group of acetic acid. A widely used progestin in menopausal hormone therapy and in progestogen-only birth control.


A branched amino heptasaccharide consisting of three repeating units of beta-D-Gal-(1->4)-[alpha-L-Fuc-(1->3)]-beta-D-GlcNAc joined by (1->3)-linkages with an alpha-L-fucosyl residue attached at the 2-position of the galactose residue at the non-reducing end.


A linear trisaccharide derivative that consists of alpha-L-fucose, beta-D-galactose and 6-sulfated D-glucose units connected in sequence by (1->2) and (1->4) links, respectively.


An amino trisaccharide in which an alpha-L-fucosyl-(1->2)-D-galactosyl unit is linked (1->4) to a 6-sulfated N-acetyl-D-glucosamine residue.


A linear heptasaccharide derivative comprising a fucose residue linked alpha(1->2) to a chain of three beta(1->3)-linked galactosyl-(1->4)-N-acetylglucosamine units.


A linear amino pentasaccharide comprising one fucose, two galactose and two glucosamine residues, one of which is at the reducing end.


An oligosaccharide derivative that is an undecasaccharide in which two tetrasaccharide branches, each formed from alpha-L-fucosyl-(1->3)-[beta-D-galactosyl-(1->4)]-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannose, are linked (1->3) and (1->6) to the mannose residue of a trisaccharide chain consisting of mannose and two N-acetylglucosamine residues all linked beta(1->4) with a beta-configuration of the anomeric carbon of the N-acetylglucosamine residue at the reducing end.


An amino disaccharide consisting of a beta-L-fucosyl residue attached to N-acetyl-beta-Dglucosamine by a (1->3)-glycosidic linkage.


An amino disaccharide consisting of an alpha-L-fucosyl residue attached to N-acetyl-beta-Dglucosamine by a (1->4)-glycosidic linkage.


UDP-N-acetylgalactosamine

A UDP-N-acetyl-D-galactosamine in which the anomeric centre of the galactosamine moiety has alpha-configuration.


cortistatins

Any member of a class of steroidal alkaloids obtained from the marine sponge Corticium simplex, with a basic skeleton that is (5R,8beta)-5,8-epoxy-9,19-cyclo-9,10-secoandrostane, bearing a dimethylamino substituent at position 3 and an isoquinolin-7-yl or isoquinolin-7-yl-derived substituent at position 17. They selectively inhibit proliferation of human umbilical vein endothelial cells (HUVECs).


mefenamic acid

An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.


cortistatin A

A member of the class of cortistatins that is substituted by hydroxy groups at positions 1 and 2, a dimethylamino group at the 3alpha position and an isoquinolin-7-yl group at the 17 position, with double bonds at the 9-11 and 10-19 positions (the 1R,2R,17beta enantiomer).


(R)-3-amino-3-phenylpropanoic acid

An optically active form of 3-amino-3-phenylpropanoic acid having R-configuration.


cortistatin B

A member of the class of cortistatins that is cortistatin A in which the hydrogen at the 16beta position has been replaced by a hydroxy group.


cortistatin C

A member of the class of cortistatins that is cortistatin A in which the hydrogens at position 16 have been replaced by an oxo group.


cortistatin D

A member of the class of cortistatins that is cortistatin C in which the hydrogen at position 17 has been replaced by a hydroxy group.


A sphingoid consisting of 3-dehydrosphinganine in which the terminal hydroxy group is replaced by a hydrogen.


A cationic sphingoid obtained by the protonation of the amino group of 1-deoxymethyl-3-dehydrosphinganine.


UDP-N,N'-diacetylbacillosamine

A UDP-amino sugar having 2,4-diacetamido-2,4,6-trideoxy-alpha-D-glucopyranose as the amino sugar component.


cortistatin E

A member of the class of cortistatins that is substituted by a dimethylamino group at the 3alpha position and a (2R)-4-(1,3-dimethylpiperidin-4-yl)butan-2-yl group at the 17 position, with double bonds at the 1-10 and 9-19 positions (the 3R,5R,17beta enantiomer).


sporulenol

A pentacyclic sesquarterpene isolated from Bacillus subtilis and formed by cyclisation of (R)-tetraprenyl-beta-curcumene (CHEBI:64801).


pyochelin I

A pyochelin that has R-stereochemistry at the thioaminal centre; the diastereoisomer with S-stereochemistry at this centre is pyochelin II. Pseudomonas aeruginosa produces a mixture of pyochelin I (major) and pyochelin II (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, enant-pyochelin I and II, are produced by Pseudomonas fluorescens.


pyochelin II

A pyochelin that has S-stereochemistry at the thioaminal centre; the diastereoisomer with R-stereochemistry at this centre is pyochelin I. Pseudomonas aeruginosa produces a mixture of pyochelin I (major) and pyochelin I (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, enant-pyochelin I and II, are produced by Pseudomonas fluorescens.


A sphingoid which is the 1-deoxymethylated derivative of 3-dehydrosphinganine.


A bioactive sphingoid which is the 1-deoxymethyl derivative of sphinganine.


A carotenoid having the structure of beta-carotene but with a cis double bond at the 9,10-position.


carlactone

A gamma-lactone that is furan-2(5H)-one which is substituted by a methyl group at position 3 and by a [(1Z,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]oxy group at position 5.


A hydroxyaldehyde in which the hydroxy group is at C-7 of (2E,4E,6E)-4-methylhepta-2,4,6-trienal.


An enal that is the 9-cis-isomer of 10'-apo-beta-carotenal.


A branched C8 alkane, comprising heptane with a methyl group attached at C-4. It has been found in Amaranth seeds.


phytocannabinoid

A class of cannabinoid which are C21 terpenophenolic compounds isolated primarily from Cannabis sativa.


endocannabinoid

A class of cannabinoids present in mammalian biological fluids and tissues that activate cannabinoid receptors.


synthetic cannabinoid

A class of cannabinoid that consists of synthetic analogs of the naturally occuring cannabinoids.


N,N'-(p-xylylidene)bis(aminoguanidine)

A guanidine derivative comprised of two carbamimidamido (guanidino) groups, each linked via one of their amino nitrogens to the imino nitrogens of 1,4-phenylenedimethanimine.


carboxynorspermidine

The non-proteinogenic L-alpha-amino acid that is norspermidine (1,5,9-triazanonane) carboxylated with S-configuration at the 2-position.


The dicarboxylic acid that is 2,3,4,5-tetrahydrodipicolinic acid hydroxylated at C-4 and with configuration 2S,4S.


geranyl acetone

A monoterpene ketone in which an (E)-geranyl group is bonded to one of the alpha-methyls of acetone. It is a component of essential oils from various plants including  Nelumbo nucifera.


pseudoionone

A terpene ketone derived from ring cleavage of the apo carotenoid beta-ionone.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of alpha-L-Rhap-(1->3)-alpha-D-GlcpNAc-1-diphospho-trans,octacis-decaprenol; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of beta-D-Galf-(1->5)-beta-D-Galf-(1->4)-alpha-L-Rhap-(1->3)-alpha-D-GlcpNAc-1-diphospho-trans,octacis-decaprenol; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of beta-D-Galf-(1->4)-alpha-L-Rhap-(1->3)-alpha-D-GlcpNAc-1-diphospho-trans,octacis-decaprenol; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of [beta-D-Galf-(1->5)-beta-D-Galf-(1->6)]14-beta-D-Galf-(1->5)-beta-D-Galf-(1->4)-alpha-L-Rhap-(1->3)-alpha-D-GlcpNAc-1-diphospho-trans,octacis-decaprenol; major species at pH 7.3.


An organic cation obtained by protonation of the three amino groups of 2'-deamino-2'-hydroxyneamine; major species at pH 7.3.


An organic cation obtained by protonation of the two amino groups of 2'-deamino-2'-hydroxy-6'-dehydroparomamine; major species at pH 7.3.


Benzamide substituted on nitrogen by a 2-hydroxyethyl group and at the 4-position by an (N-methylpiperidinio)methyl group.


conduritol

A tetrol that is cyclohexene in which a hydrogen attached to each of the carbons at positions 3, 4, 5, and 6 is replaced by a hydroxy group. The group consists of six possible diastereoisomers, known as conduritols A to F, some of which can exist as two distinct enantiomers.


A piperidinium ion that is benzamide substituted on nitrogen by a 2-hydroxyethyl group and at the 4-position by a [3-(4-carboxybutanamido)-N-methylpiperidinio]methyl group.


megestrol

A 3-oxo Delta(4)-steroid that is pregna-4,6-diene-3,20-dione substituted by a methyl group at position 6 and a hydroxy group at position 17.


An amino oligosaccharide that is a tridecasaccharide derivative in which two pentasaccharide branches, each formed from N-acetyl-alpha-D-galactosaminyl-(1->3)-[alpha-L-fucosyl-(1->2)]-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannose, are linked (1->3) and (1->6) to the mannose residue of a trisaccharide chain consisting of mannose and two N-acetylglucosamine residues all linked beta(1->4) with a beta-configuration of the anomeric carbon of the N-acetylglucosamine residue at the reducing end.


conduritol A

A conduritol in which the hydroxy groups at positions 2, 3, and 4 are in a trans,trans,cis- relationship to that at position 1.


conduritol B

A racemate consisting of the two possible cyclohex-5-ene-1,2,3,4-tetrols in which the hydroxy groups at positions 2, 3, and 4 are in a trans,cis,trans- relationship to that at position 1.


An amino cyclitol glycoside that is 2-deoxystreptamine in which the pro-R hydroxy group is substituted by a 6-amino-6-deoxy-alpha-D-glucosyl residue.


(+)-conduritol B

A conduritol which has 1S,2R,3R,4S configuration.


An amino cyclitol glycoside that is 2-deoxystreptamine in which the pro-R hydroxy group is substituted by a 6-dehydro-alpha-D-glucosyl residue.


(-)-conduritol B

A conduritol which has 1R,2S,3S,4R configuration.


beta-carotene 15,15'-epoxide

An epoxycarotenoid obtained by epoxidation across the 15,15'-double bond of beta-carotene.


A carotenol obtained by formal dihydroxylation across the 15,15'-double bond of beta-carotene.


conduritol B epoxide

A racemate comprising the 1-D- and 1-L- enantiomers of 1,2-anhydro-myo-inositol.


megestrol acetate

A steroid ester resulting from the formal condensation of the hydroxy group of megestrol with the carboxy group of acetic acid. It is an appetite stimulant used for the treatment of anorexia and cachexia. Also used for birth control and for the treatment of breast cancer.


CONDURITOL B EPOXIDE

A conduritol epoxide resulting from the formal epoxidation of the double bond of (+)-conduritol B.


A conduritol epoxide resulting from the formal epoxidation of the double bond of (-)-conduritol B.


conduritol epoxide

An epoxide resulting from the epoxidation of the double bond of a conduritol.


attenoside

An acyclic diterpene glycoside consisting of a 20-hydroxygeranyllinalool skeleton conjugated to two disaccharide units at C-3 and C-20.


An oxysterol that is the 22R-hydroxy derivative of cholesterol.


A monocarboxylic acid comprised of hexanoic acid substituted on C-6 by a 4-[(2S)-2-(methylamino)propyl]phenyl group.


lyciumoside IV

An acyclic diterpene glycoside consisting of a 20-hydroxygeranyllinalool skeleton conjugated to a glucosyl residue at C-20 and a rhamnosylglucosyl moiety at C-3.


A polyprenyl glycosyl phosphate consisting of beta-D-galactofuranosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-N-acetyl-alpha-D-glucosamine attached at the 1-position to trans,octacis-decaprenyl phosphate.


nicotianoside I

An acyclic diterpene glycoside consisting of a 20-hydroxygeranyllinalool skeleton conjugated to a malonylglucosyl residue at C-20 and a rhamnosylglucosyl moiety at C-3.


nicotianoside II

An acyclic diterpene glycoside consisting of a 20-hydroxygeranyllinalool skeleton conjugated to a malonylglucosyl residue at C-20 and a rhamnosyl(malonyl)glucosyl moiety at C-3.


(-)-Lariciresinol

A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2R,3S,4S-diastereomer).


(+)-PINORESINOL

An enantiomer of pinoresinol having (-)-1R,3aS,4R,6aS-configuration.


LARICIRESINOL

A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).


(+)-secoisolariciresinol

An enantiomer of secoisolariciresinol having (+)-(2S,3S)-configuration.


An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of 4-(3-methylbut-2-enyl)-L-abrine.


N-acetylcarnosine

A dipeptide that is the N-acetyl derivative of carnosine.


secoisolariciresinol

A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups


beta-damascenone

A cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group.


FARNESYLACETOL

A terpene ketone in which an (E,E)-farnesyl group is bonded to one of the alpha-methyls of acetone.


A polyprenyl glycosyl phosphate consisting of alpha-L-rhamnosyl-(1->3)-N-acetyl-alpha-D-glucosamine attached at the 1-position to trans,octacis-decaprenyl phosphate.


3-(2-methoxyethoxy)propanoic acid

A monocarboxylic acid that is propanoic acid substituted at C-3 by a 2-methoxyethoxy group.


2-(2-methoxyethoxy)propanoic acid

A monocarboxylic acid that is propanoic acid substituted at C-2 by a 2-methoxyethoxy group.


A polyprenyl glycosyl phosphate consisting of beta-D-galactofuranosyl-(1->5)-beta-D-galactofuranosyl-(1->4)-alpha-L-rhamnosyl-(1->3)-N-acetyl-alpha-D-glucosamine attached at the 1-position to trans,octacis-decaprenyl phosphate.


A 4-hydroxyproline substituted at N-1 by an ethoxycarbonyl group.


An epoxide resulting from the formal epoxidation of the double bond between positions 2 and 3 of geranial.


A 4-hydroxyproline substituted at N-1 by an methoxyacetyl group.


geranate

An unsaturated fatty acid anion that is the conjugate base of geranic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


An acyl-CoA oxoanion arising from deprotonation of phosphate, diphosphate and carboxylic acid functions of 2,3-dehydroadipyl-CoA.


dihydrocurcumin

A beta-diketone that is curcumin in which one of the double bonds has been reduced to a single bond.


TETRAHYDROCURCUMIN

A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.


geranic acid

A polyunsaturated fatty acid that is octa-2,6-dienoic acid bearing two methyl substituents at positions 3 and 7 (the 2E-isomer).


beta-diketone

A diketone in which the two keto groups are separated by a single carbon atom.


An apo carotenoid monoterpenoid that is alpha-ionone with a hydroxy substituent at position 3.


HIV-1 integrase inhibitor

An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.


cyclo(L-leucyl-L-leucyl)

A member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione in which one hydrogen at position 3 and one hydrogen at position 6 are replaced by isobutyl groups (the 3S,6S-diastereomer).


glucoheptonic acid

A carbohydrate acid that is heptanoic acid substituted by hydroxy groups at C-2, C-3, C-4, C-5, C-6, and C-7.


An organic heterotricyclic compound that is [1,2,4]triazolo[3,4-f][1,6]naphthyridin-3(2H)-one substituted at positions 8 and 9 respectively by 4-(1-aminocyclobutyl)phenyl and phenyl groups.


perifosine

A phospholipid consisting of 1,1-dimethylpiperidinium-4-yl hydrogen phosphate in which the hydrogen is replaced by a stearyl (octadecyl) group.


Any 1,4-benzoquinone carrying a single hydroxy substituent.


lysophosphatidylethanolamine zwitterion

A zwitterion obtained by transfer of a proton from the phosphate to the amino group of any lysophosphatidylethanolamine. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl.


An amino oligosaccharide that is a branched decasaccharide derivative comprised of a mannose residue to which is linked an N-acetylgalactosaminyl residue at O-2, a glucosyl residue at O-3 and a beta-D-QuiN4Fm-(1->4)-alpha-D-GalNAcAN-(1->4)-alpha-D-GalNAcAN-(1->3)-beta-D-QuiNAc tetrasaccharide chain at O-4, all linked to an [alpha-D-Glc-(1->2)]-alpha-D-Man-(1->5)-alpha-Kdo branched trisaccharide unit.


AZADIRADIONE

A  tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities.


NIMBOCINOL

A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by a oxo groups at positions 3 and 16, a hydroxy group at position 7 and a furan-3-yl group at position 17. It has been isolated from Azadirachta indica.


A  limonoid that is the benzoate ester of nimbocinol. It has been isolated from Azadirachta indica.


A limonoid that is azadiradione substituted by a hydroxy group at position 15. It has been isolated from Azadirachta indica.


A limonoid that is azadiradione substituted by a hydroxy group at position 17. It has been isolated from Azadirachta indica.


EPOXYAZADIRADIONE

A limonoid that is  azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes.


A  limonoid that is  epoxyazadiradione in which the acetyl group has been replaced by a benzoyl group. It has been isolated from Azadirachta indica.


A  limonoid that is the C-17 epimer of azadiradione. It has been isolated from Azadirachta indica.


A limonoid that is 17-epiazadiradione substituted by a hydroxy group at position 17. Isolated from Azadirachta indica, it exhibits antineoplastic activity.


A limonoid that is 4,4,8-trimethylandrosta-1,16-diene substituted by a furan-3-yl group at position 17, oxo groups at positions 3 and 15, a hydroxy group at position 16 and an acetoxy group at position 7. It has been isolated from Azadirachta indica.


azadiradionolide

A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by a oxo groups at positions 3 and 16, an acetoxy group at position 7 and a 2-oxo-2,5-dihydrofuran-3-yl group at position 17. It has been isolated from Azadirachta indica.


A limonoid that is 20,21,22,23-tetrahydroazadirone substituted by an additional oxo group at position 23. It has been isolated from Azadirachta indica.


DESFURANOAZADIRADIONE

A limonoid that is azadiradione in which the furanyl group at position 17 is replaced by a hydrogen. It has been isolated from Azadirachta indica.


DIACETYLVILASININ

A limonoid found in Azadirachta indica.


3-acetyl-7-tigloylvilasinin lactone

A limonoid found in Azadirachta indica.


DEACETYLGEDUNIN

A limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica.


A limonoid that is gedunin in which the acetoxy group at position 7 is replaced by a benzoyloxy group. Isolated from Azadirachta indica, it exhibits cytotoxic activity against HL60 leukemia cells.


NIMOLICINOL

A limonoid found in Azadirachta indica.


vepaol

A limonoid found in Azadirachta indica.


A limonoid that is the C-23 epimer of vepaol. It has been isolated from Azadirachta indica.


NIMBIN

A limonoid found in Azadirachta indica.