| 11-hydroxytestosterone | An androstanoid that is testosterone carrying an additional hydroxy substituent at the 11beta-position. | 11beta-hydroxytestosterone |
| 2-bromophenol | | 2-bromophenol |
| 2,4-di-tert-butylphenol | A member of the class of phenols carrying two tert-butyl substituents at positions 2 and 4. | 2,4-di-tert-butylphenol |
| 2,4-dibromophenol | A bromophenol that is phenol in which the hydrogens at positions 2 and 4 have been replaced by bromines. | 2,4-dibromophenol |
| 2,4,6-tribromophenol | A bromophenol that is phenol in which the hydrogens at positions 2, 4 and 6 have been replaced by bromines. It is commonly used as a fungicide and in the preparation of flame retardants. | 2,4,6-tribromophenol |
| 2,6-dibromophenol | A dibromophenol that is phenol in which both of the hydrogens that are ortho to the phenolic hydroxy group have been replaced by bromines. | 2,6-dibromophenol |
| 4-amino-2,6-dinitrotoluene | An amino-nitrotoluene that is 2,6-dinitrotoluene substituted at position 4 by an amino group. | 4-amino-2,6-dinitrotoluene |
| 4-bromophenol | A bromophenol containing only hydroxy and bromo substituents that are para to one another. | 4-bromophenol |
| 4-hydroxyretinal | A retinoid that is all-trans-retinal carrying a hydroxy substituent at position 4 on the cyclohexenyl ring. | all-trans-4-hydroxyretinal |
| 6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene | | (+)-halomon |
| acetopyrrothine | A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. | thiolutin |
| adefovir | A dimeric naphthopyran with formula C32H26O10, originally isolated from Aspergillus niger. | aurasperone A |
| adonixanthin | A carotenone that consists of beta,beta-caroten-4-one bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'R diastereomer). | adonixanthin |
| adrenosterone | A 3-oxo Delta(4)-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17. | adrenosterone |
| Ala-Lys | A dipeptide obtained by formal condensation of the carboxy group of L-alanine with the alpha-amino group of L-lysine. | Ala-Lys |
| albicanol | A drimane-type sesquiterpenoid orginally isolated from the liverwort Diplophyllum albicans. It exhibits fish antifeedant, antifungal and antineoplastic activities. | (+)-albicanol |
| allocholic acid | An allo-bile acid that is 5alpha-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12. | allocholic acid |
| altritol | A hexitol that is hexane-1,2,3,4,5,6-hexol having (2R,3R,4S,5R) configuration; the D-enantiomer of altritol. | D-altritol |
| antheraxanthin | An epoxycarotenol that is beta-carotene-3,3'-diol in which one of the one of the endocyclic double bonds has been oxidised to the corresponding epoxide. It is a neutral yellow plant pigment found in Euglenophyta. | antheraxanthin |
| aplysiatoxin | The parent member of the class of aplysiatoxins. It is a cyanotoxin produced by several species of freshwater and marine cyanobacteria, as well as algae and molluscs. | aplysiatoxin |
| arsenocholine | An arsonium ion that is choline in which the central nitrogen has been replaced by arsenic. | arsenocholine |
| aspulvinone E | A 4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one in which the double bond adopts a Z-configuration. It is a marine metabolite isolated from the fungus Aspergillus terreus and exhibits antiviral activity. | aspulvinone E |
| beta-aminoglutaric acid | A 1,5-dicarboxylic acid compound having a 3-amino substituent. It has been isolated from the extracts of the algae, Chondria armata. | isoglutamic acid |
| brassicasterol | An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. | brassicasterol |
| bromodeoxytopsentin | An aromatic ketone that is imidazole which is substituted by a 1H-indole-3-carbonyl group and a 6-bromo-1H-indol-3-yl group at positions 2 and 4, respectively. Isolated from the Mediterranean shallow-water sponge, Topsentia genetrix. It is a potent inhibitor of MRSA pyruvate kinase and exhibits antibacterial properties. | bromodeoxytopsentin |
| bryostatin 1 | A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins. | bryostatin 1 |
| bryostatin 2 | A member of the class of bryostatins that is bryostatin 1 in which the acetoxy group has been replaced by a hydroxy group. | bryostatin 2 |
| caldopentamine | A polyazaalkane that is the 1,5,9,13,17-pentaaza derivative of heptodecane. | caldopentamine |
| cerulomycin | A pyridine alkaloid that is 2,2'-bipyridine substituted by a methoxy group at position 4 and a (E)-(hydroxyimino)methyl group at position 6. Isolated from the marine-derived actinomycete Actinoalloteichus cyanogriseus, it exhibits antineoplastic activity. | caerulomycin A |
| chrysogine | | chrysogine |
| crambescidin 800 | An organic heteropentacyclic guanidine alkaloid isolated from the marine sponge Crambe crambe and Batzella. It exhibits anti-HIV-1 and anti-HSV-1 activity. | crambescidin 800 |
| cyclo(leucyl-prolyl) | A homodetic cyclic peptide composed from leucyl and prolyl residues. | cyclo(L-Leu-L-Pro) |
| debromoaplysiatoxin | A member of the class of aplysiatoxins that has the structure of the parent aplysiatoxin, but is lacking the bromo substituent on the benzene ring at the position para to the phenolic hydroxy group. It is a cyanotoxin produced by several species of freshwater and marine cyanobacteria, as well as algae and molluscs. | debromoaplysiatoxin |
| decarbamylsaxitoxin | A pyrrolopurine that is 2,6-diiminodecahydropyrrolo[1,2-c]purine carrying an additional hydroxymethyl substituent at position 4 as well as two hydroxy substituents at position 10. A toxin that is isolated from marine dinoflagellates and cyanobacteria and is known to cause paralytic shellfish poisoning. | decarbamoylsaxitoxin |
| deferrioxamine e | A cyclic hydroxamic acid siderophore that is produced by several bacterial species and exhibits antitumour activity. | desferrioxamine E |
| dibromoacetic acid | A monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are replaced by bromo groups. | dibromoacetic acid |
| dibromophakellin | An alkaloid isolated from the marine sponge Phakellia flabellata and Acanthella costata. It acts as an alpha2B adrenoceptor agonist. | (-)-dibromophakellin |
| dichloroacetic acid | An organochlorine compound comprising acetic acid carrying two chloro substituents at the 2-position. It occurs in nature in seaweed, Asparagopsis taxiformis. | dichloroacetic acid |
| dimethyl sulfide | A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae. | dimethyl sulfide |
| dimethylpropiothetin | A sulfonium betaine obtained by deprotonation of the carboxy group of 3-dimethylsulfoniopropionic acid. | S,S-dimethyl-beta-propiothetin |
| dinophysistoxin 1 | A ketal that is a marine toxin structurally related to okadaic acid. Produced by dinoflagellates it is known to accumulate in shellfish and cause diarrhoeic shellfish poisoning. It is an inhibitor of serine/threonine protein phosphatases 1 (PP1) and PP2A and has been shown to promote cancer cell growth in tumour cell lines and animal models. | dinophysistoxin 1 |
| diorcinol | An aromatic ether that is diphenyl ether in which both phenyl groups are substituted at position 3 by a hydroxy group and at position 5 by a methyl group. | diorcinol |
| dolastatin 10 | A tetrapeptide that is isolated from the sea hare Dolabella auricularia. It is a potent anticancer agent which inhibits tubulin polymerization. | dolastatin 10 |
| domoic acid | An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP). | domoic acid |
| dysidenin | A secondary carboxamide resulting from the formal condensation of the carboxy group of (4S)-5,5,5-trichloro-N-methyl-N-[(3S)-4,4,4-trichloro-3-methylbutanoyl]-L-leucine with the amino group of (1S)-1-(1,3-thiazol-2-yl)ethanamine. It is a marine metabolite initially isolated from the sponge dysidea herbacea. | dysidenin |
| dysiherbaine | A furopyran that is (3aR,7aR)-hexahydro-2H-furo[3,2-b]pyran substituted by carboxy, (2S)-2-amino-2-carboxyethyl, hydroxy and methylamino groups at positions 2, 2, 6, and 7, respectively (the 2R,3aR,6S,7R,7aR-stereoisomer). A convulsant isolated from the marine sponge Dysidea herbacea that has high affinity for kainate ionotropic glutamate receptors. | dysiherbaine |
| echinenone | A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. | echinenone |
| echinuline | An indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species. | echinulin |
| ecteinascidin 743 | A tetrahydroisoquinoline alkaloid obtained from a Caribbean tunicate Ecteinascidia turbinata. Used for the treatment of soft tissue sarcoma and relapsed ovarian cancer. | trabectedin |
| emindole SB | | emindole SB |
| epipinoresinol | An enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. | epipinoresinol |
| ethylene dibromide | A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae. | 1,2-dibromoethane |
| flavasperone | A naphtho-gamma-pyrone that is 4H-naphtho[1,2-b]pyran-4-one carrying a methyl substituent at position2, a hydroxy substituent at position 5 and two methoxy substotuents at positions 8 and 10. Originally isolated from Aspergillus niger. | flavasperone |
| fonsecin | A naphtho-gamma-pyrone that is 2,3-dihydro-4H-benzo[g]chromen-4-one bearing a methyl substituent at position 2, a methoxy substituent at position 6 and three hydroxy substituents at positions 2, 5 and 8. | fonsecin |
| gamma-sitosterol | A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. | clionasterol |
| geographutoxin i | | Gonyautoxin I |
| gonyautoxin ii | | Gonyautoxin 2 |
| gonyautoxin v | | Gonyautoxin 5 |
| holomycin | A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties. | holomycin |
| iejimalide b | A macrolide that is isolated from the marine tunicate Eudistoma cf. rigida and exhibits potent in vitro cytotoxic activity. | lejimalide B |
| indole-3-carbaldehyde | A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group. | indole-3-carbaldehyde |
| jaspamide b | A cyclodepsipeptide isolated from Jaspis splendens. A derivative of jaspamide, it exhibits anti-tumour activity. | jaspamide B |
| jasplakinolide | A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer. | jaspamide |
| laulimalide | A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp. | laulimalide |
| manumycin | A polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties. | manumycin A |
| 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 A |
| 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 A |
| massadine | An alkaloid isolated from Stylissa massa. | massadine |
| meso-zeaxanthin | A carotenol that is beta,beta-carotene carrying two hydroxy substituents at positions 3 and 3' (the 3R,3'S-diastereomer). It is rarely found in diet and is believed to be formed at the macula by metabolic transformations of ingested carotenoids. | meso-zeaxanthin |
| methyl bromide | A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae. | bromomethane |
| methyl chloride | A one-carbon compound that is methane in which one of the hydrogens is replaced by a chloro group. | chloromethane |
| methylene bromide | A member of the class of bromomethanes that is methane substituted by two bromo groups. It is produced by marine algae. | dibromomethane |
| muromonab-cd3 | An organic heteropentacyclic compound that is isolated from the marine sponge Xestospongia exigua. | xestospongin C |
| n-acetyldopamine | A secondary carboxamide obtained by formal condensation of the carboxy group of acetic acid with the amino group of dopamine. A dopamine metabolite. | N-acetyldopamine |
| n-acetyltyramine | A member of the class of tyramines that is tyramine in which one of the hydrogens of the amino group is replaced by an acetyl group. | N-acetyltyramine |
| n-palmitoylglycine | An N-acylglycine in which the acyl group is specified as hexadecanoyl (palmitoyl). | N-hexadecanoylglycine |
| neodysiherbaine a | A furopyran that is (3aR,7aR)-hexahydro-2H-furo[3,2-b]pyran substituted by carboxy, (2S)-2-amino-2-carboxyethyl, hydroxy and hydroxy groups at positions 2, 2, 6, and 7, respectively (the 2R,3aR,6R,7R,7aR-stereoisomer). A convulsant isolated from the marine sponge Dysidea herbacea. | neodysiherbaine A |
| norharman | The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring. | beta-carboline |
| norsalsolinol | An isoquinolinol that is 1,2,3,4-tetrahydroisoquinoline substituted by hydroxy groups at positions 6 and 7. It is present in the dopamine-rich areas of the human brain, including the substantia nigra. | norsalsolinol |
| okadaic acid | A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells. | okadaic acid |
| orsellinic acid | A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group. | o-orsellinic acid |
| ovothiol a | A L-histidine derivative that is L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively. | ovothiol A zwitterion; ovothiol A |
| ovothiol c | A L-histidine derivative that is N,N-dimethyl-L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively. | ovothiol C zwitterion; ovothiol C |
| papuamide b | A cyclodepsipeptide that is isolated from Papua New Guinea collections of the marine sponges Theonella mirabilis and Theonella swinhoei. It exhbits anti-HIV-1 activity and cytotoxicity against some human cancer cell lines. | papuamide B |
| pateamine a | A marine macrodiolide that is isolated from the sponge Mycale hentscheli and exhibits anticancer and antiviral properties | pateamine |
| pectenotoxin 1 | | Pectenotoxin 1 |
| pectenotoxin 2 | | Pectenotoxin 2 |
| pectenotoxin 6 | | Pectenotoxin 7 |
| plitidepsin | A didemnin that is didemin B in which the hydroxy group of the 1-(2-hydroxypropanoyl)-L-prolinamide moiety has been oxidised to the corresponding ketone. It was originally isolated from the Mediterranean tunicate Aplidium albicans. | plitidepsin |
| pyoluteorin | A member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. | pyoluteorin |
| pyranonigrin a | A member of the class of pyranopyrroles that is 2-[(1E)-prop-1-en-1-yl]-6,7-dihydropyrano[2,3-c]pyrrole-4,5-dione carrying two additional hydroxy substituents at positions 3 and 7. Originally isolated from Aspergillus niger. | pyranonigrin A |
| saxitoxin | An alkaloid isolated from the marine dinoflagellates and cyanobacteria that causes paralytic shellfish poisoning. | saxitoxin |
| scalaradial | A scalarane sesterterpenoid with formula C27H40O4. It is a natural product found in the marine sponges Spongia officinalis and Cacospongia mollior, and exhibits anti-inflammatory activity. | scalaradial |
| t-muurolol | A cadinane sesquiterpenoid that consists of 4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene having a hydroxy substituent at position 1 and (1S,4S,4aR,8aS)-configuration. | (-)-Tau-muurolol |
| tetrodotoxin | A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels. | tetrodotoxin |
| tropodithietic acid | A monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations. | tropodithietic acid |
| vanchrobactin | A catechol-type natural product that is composed of 2,3-dihydroxybenzoic acid, D-arginine and L-serine joined in sequence by peptide linkages. It is a siderophore synthesized by the bacterial fish pathogen Vibrio anguillarum. | vanchrobactin |
| vibrioferrin | A tricarboxylic acid that is citric acid in which the pro-R carboxy group has been esterified with the primary hydroxy group of 2-hydroxy-1-{(2S)-1-[(2-hydroxyethyl)amino]-1-oxopropan-2-yl}-5-oxoproline. It is a siderophore isolated from bacteria closely associated or symbiotic with toxic, bloom-forming dinoflagellates. | vibrioferrin |
| viridicatin | A hydroxyquinolone that is 3-hydroxyuinolin-2(1H)-one which is substituted at position 4 by a phenyl groups. Isolated from the mycelium of several Penicillium species, it exhibits strong antibiotic activity against M. tuberculosis and also against B. subtilis, S. aureus and S. cerevisiae. | viridicatin |