| Member | Definition | Role |
|---|
| actinodaphine | An organic heteropentacyclic compound 6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline bering additional hydroxy and methoxy substituents at positions 10 and 11 respectively. | actinodaphnine |
| akuammicine | A monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major. | akuammicine |
| alexa fluor 546 | | Alexa Fluor 546 |
| amberlite cg 400 | | methyl 17-hydroxy-20xi-yohimban-16-carboxylate |
| anonaine | An aporphine alkaloid that exhibits anti-cancer, trypanocidal and antiplasmodial activites. | (-)-annonaine |
| antofine | An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities. | (-)-antofine |
| averufin | An organic heteropentacyclic compound that is 3,4,5,6-tetrahydro-2H-2,6-epoxyanthra[2,3-b]oxocine-8,13-dione substituted at position 2 by a methyl group and at positions 7, 9 and 11 by hydroxy groups (the S,S-diastereomer) | (1'S,5'S)-averufin |
| berberine | | berberine |
| butaclamol | | LSM-20934 |
| butaclamol | An organic heteropentacyclic compound that is 2,3,4,4a,8,9,13b,14-octahydro-1H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinoline substituted at position 3 by both hydroxy and tert-butyl groups. | (+)-butaclamol |
| cafestol | An organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction). | cafestol |
| calcein am | An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases. | calcein am |
| canadine | A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10. | canadine |
| catharanthine | An organic heteropentacyclic compound and monoterpenoid indole alkaloid produced by the medicinal plant Catharanthus roseus via strictosidine. | catharanthine |
| cephalotaxine | A benzazepine alkaloid isolated from Cephalotaxus harringtonia. | cephalotaxine |
| chetomin | An organic heteropentacyclic compound of the class of epipolythiodioxopiperazine. Isolated from Chaetomium globosum and Farrowia seminuda, it exhibits immunosuppressive activity. | chetomin |
| chrodrimanin b | | chrodrimanin B |
| codeine | A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties. | codeine |
| coronardine | A monoterpenoid indole alkaloid with formula C21H26N2O2. It is isolated from the flowering plant genus, Tabernaemontana. | (-)-coronaridine |
| 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 |
| cryptopleurine | An organic heteropentacyclic compound that is (14aR)-11,12,13,14,14a,15-hexahydro-9H-dibenzo[f,h]pyrido[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. | cryptopleurine |
| deguelin | A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. | deguelin |
| demethoxyfumitremorgin c | An organic heteropentacyclic compound that is a mycotoxic indole alkaloid, consisting of fumitremorgin C lacking the 9-methoxy substituent. | demethoxyfumitremorgin C |
| deserpidine | | deserpidine |
| diflomotecan | An organic heteropentacyclic compound that is (5R)-8-[(6,7-difluoroquinolin-3-yl)methyl]-5-ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine moiety is joined to position 3 of the difluoroquinoine ring by a single bond. An E-ring modified camptothecin analogue that has greater lactone stability in plasma compared with other topoisomerase I inhibitors. | diflomotecan |
| ebc-46 | A diterpenoid natural product isolated from the kernels of the Australian blushwood tree (Fontainea picrosperma). It is approved as a veterinary pharmaceutical for the treatment of non-metastatic and non-resectable canine mast cell tumours. | tigilanol tiglate |
| eckstolonol | A phlorotannin that is [1,4]benzodioxino[2,3-a]oxanthrene substituted by hydroxy groups at positions 1, 3, 6, 9 and 11. Isolated from the brown alga Ecklonia stolonifera, it exhibits radical scavenging activity. | eckstolonol |
| eplerenone | | eplerenone |
| eurycomanone | A quassinoid isolated from Eurycoma longifolia and has been shown to exhibit antineoplastic and antimalarial activties. | eurycomanone |
| fluocinolone acetonide | A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. | fluocinolone acetonide |
| fluorescein | A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy. | fluorescein (lactone form) |
| fumitremorgin b | An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi via a tryptophan-proline diketopiperazine intermediate. | fumitremorgin B |
| gallein | A xanthene dye that is fluoran carrying four hydroxy substituents at positions 3', 4', 5' and 6'. | gallein |
| gedunin | A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata. | gedunin |
| geissospermine | A indole alkaloid comprising two indole-derived polycyclic moieties joined by a cyclic ether linkage. | geissospermine |
| gibberellic acid | A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4. | gibberellin A3 |
| glaucarubinone | A quassinoid with formula C25H34O10. It is a natural product isolated from several plant species and exhibits anti-cancer and anti-malarial properties. | glaucarubinone |
| glyceollin | | glyceollin |
| gs-5816 | A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes. | velpatasvir |
| hippeastrine | An indole alkaloid isolated from the Amaryllidaceae family and has been shown to exhibit cytotoxic activity. | hippeastrine |
| homocamptothecin | An organic heteropentacyclic compound that is (5R)-5-ethyl-5-hydroxy-8-(quinolin-3-ylmethyl)-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine group has been joined to position 2 of the quinoline ring by a single bond. A semisynthetic analogue of camptothecin, it is an inhibitor of topoisomerase I. | (R)-homocamptothecin |
| homoharringtonine | A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia. | omacetaxine mepesuccinate |
| hydrocodone | A morphinane-like compound that is a semi-synthetic opioid synthesized from codeine. | hydrocodone |
| hydromorphone | A morphinane alkaloid that is a hydrogenated ketone derivative of morphine. A semi-synthetic drug, it is a centrally acting pain medication of the opioid class. | hydromorphone |
| interiotherin b | A lignan with a dibenzocyclooctadiene skeleton attached to a fatty acid ester side chain. It is isolated from Kadsura interior and has been shown to exhibit anti-HIV activity. | interiotherin B |
| jadomycin b | A jadomycin that is jadomycin A in which the phenolic hydroxy group at position 12 has been converted to the corresponding 2,6-dideoxy-alpha-L-ribo-hexopyranoside, isolated from Streptomyces venezuelae. It exists as a diastereoisomeric mixture consisting of both 3aS and 3aR isomers. | jadomycin B |
| kahweol | A diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties. | kahweol |
| liriodenine | An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities. | liriodenine |
| morphine | A morphinane alkaloid that is a highly potent opiate analgesic psychoactive drug. Morphine acts directly on the central nervous system (CNS) to relieve pain but has a high potential for addiction, with tolerance and both physical and psychological dependence developing rapidly. Morphine is the most abundant opiate found in Papaver somniferum (the opium poppy). | morphine |
| muromonab-cd3 | An organic heteropentacyclic compound that is isolated from the marine sponge Xestospongia exigua. | xestospongin C |
| nalbuphine | | nalbuphine |
| naloxegol | An organic heteropentacyclic compound that is naloxone in which the keto group is replaced by a PEG moiety. Used for treatment of opioid-induced constipation. | naloxegol |
| naloxone | A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose. | naloxone |
| naltrexone | An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence. | naltrexone |
| neopine | A morphinane alkaloid that is the Delta(8,14) isomer of codeine. It is a minor constituent in opium from Papaver somniferum. | neopine |
| noribogaine | An organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a hydroxy group. It is the primary (and long-lived) metabolite of ibogaine, the psychoactive indole alkaloid found in the African rainforest shrub Tabernanthe iboga. | noribogaine |
| oridonin | An organic heteropentacyclic compound and ent-kaurane diterpenoid with formula C20H28O6 isolated from the leaves of the medicinal herb Rabdosia rubescens. | oridonin |
| oripavine | A morphinane alkaloid with formula C18H19NO3. It is the major metabolite of thebaine. | oripavine |
| oxycodone | A semisynthetic opioid of formula C18H21NO4 that is derived from thebaine. It is a moderately potent opioid analgesic, generally used for relief of moderate to severe pain. | oxycodone |
| pholcodine | A morphinane alkaloid that is a derivative of morphine with a 2-morpholinoethyl group at the 3-position. | pholcodine |
| picrinine | A natural product with formula C20H22N2O3 that is the member of the akuammiline family of alkaloids, first isolated in 1965 from the leaves of Alstonia scholaris. | picrinine |
| picrotin | An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. | picrotin |
| picrotoxinin | A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. | picrotoxinin |
| raubasine | A monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure. | ajmalicine |
| rescinnamine | | rescinnamine |
| resiniferatoxin | A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1). | resiniferatoxin |
| rotenone | A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). | rotenone |
| salannin | A limonoid with insecticidal activity isolated from Azadirachta indica. | salannin |
| siccanin | | Siccanin |
| simalikalactone D | A quassinoid isolated from Quassia amara and Quassia africana. It has been shown to exhibit antimalarial, cytotoxic and antiviral activities. | simalikalactone D |
| sporidesmin | An organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation disease facial eczema in ruminants. | sporidesmin A |
| stanozolol | An organic heteropentacyclic compound resulting from the formal condensation of the 3-keto-aldehyde moiety of oxymetholone with hydrazine. Like oxymetholone, it is a synthetic anabolic steroid. It has both anabolic and androgenic properties, and has been used to treat hereditary angioedema and various vascular disorders. It has also been widely abused by professional athletes. | stanozolol |
| tabersonine | A monoterpenoid indole alkaloid with cytotoxic activity. | tabersonine |
| tephrosin | A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities. | tephrosin |
| tetrahydroalstonine | A heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species. | tetrahydroalstonine |
| thebaine | | thebaine |
| triphosphate | An indole alkaloid that is sarpagan in which the methyl group attached to position 16 has been oxidised to the corresponding aldehyde. | vellosimine |
| tryptoquivaline | An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter. | fumitremorgin C |
| tylophorine | | Tylophorine |
| versicolorin a | An organic heteropentacyclic compound that is 3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione carrying three hydroxy substituents at positions 4, 6 and 8. | versicolorin A |
| versicolorin c | An organic heteropentacyclic compound that is 2,3,3a,12a-tetrahydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione carrying three hydroxy substituents at positions 4, 6 and 8. | versicolorin B |
| vincaleukoblastine | | vincaleukoblastine |
| vincamine | | vincamine |
| vincristine | A vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer. | vincristine |
| vindesine | | vindesine |
| vindolinine | A monoterpenoid indole alkaloid with formula C21H24N2O2, isolated from several plant species. | vindolinine |
| vinflunine | An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethyl group attached to this ring has been replaced by a 1,1-difluoroethyl group. | vinflunine |
| vinorelbine | A vinca alkaloid with a norvinblastine skeleton. | vinorelbine |
| voacamine | A monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species. | (-)-voacangine |
| wilforgine | A dihydroagarofuran sesquiterpenoid and pyridine alkaloid with formula C41H47NO19 originally isolated from the roots of Tripterygium wilfordii. | wilforgine |
| wortmannin | | wortmannin |