1.0 2010-04-08 22:04:41 UTC 2025-11-18 22:22:03 UTC FDB000742 Gossypol Gossypol, also known as gossypol, (+)-isomer or (-)-gossypol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, gossypol is considered to be an isoprenoid lipid molecule. Gossypol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gossypol can be found in cottonseed, okra, soy bean, and sunflower, which makes gossypol a potential biomarker for the consumption of these food products. Gossypol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Among other things, it has been tested as a male oral contraceptive in China. In addition to its putative contraceptive properties, gossypol has also long been known to possess antimalarial properties. Other researchers are investigating the anticancer properties of gossypol . Gossypol may cause apoptosis via the regulation of Bax and Bcl-2 proteins. It is also an inhibitor of calcineurin and protein kinases C, and has been shown to bind calmodulin (L1239) (T3DB). 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 9CI Thespesin C30H30O8 518.5544 518.194067936 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde (-)-gossypol 303-45-7 CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3 QBKSWRVVCFFDOT-UHFFFAOYSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aromatic homopolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Aryl-aldehydes Hydrocarbon derivatives Naphthols and derivatives Organic oxides Polyols Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid 1-naphthol 2-naphthol Aldehyde Aromatic homopolycyclic compound Aryl-aldehyde Benzenoid Cadinane sesquiterpenoid Hydrocarbon derivative Naphthalene Organic oxide Organic oxygen compound Organooxygen compound Polyol Sesquiterpenoid Vinylogous acid Cadinane sesquiterpenoids Cadinane sesquiterpenoids Cadinanes Terpenoids polyphenol logp 4.49 ALOGPS logs -5.13 ALOGPS solubility 3.85e-03 g/l ALOGPS logp 8.02 ChemAxon pka_strongest_acidic 7.8 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde ChemAxon average_mass 518.5544 ChemAxon mono_mass 518.194067936 ChemAxon smiles CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C ChemAxon formula C30H30O8 ChemAxon inchi InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3 ChemAxon inchikey QBKSWRVVCFFDOT-UHFFFAOYSA-N ChemAxon polar_surface_area 155.52 ChemAxon refractivity 147.61 ChemAxon polarizability 55.95 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 77448 Specdb::MsMs 77449 Specdb::MsMs 77450 Specdb::MsMs 137577 Specdb::MsMs 137578 Specdb::MsMs 137579 Specdb::MsMs 2798021 Specdb::MsMs 2798022 Specdb::MsMs 2798023 Specdb::MsMs 2880929 Specdb::MsMs 2880930 Specdb::MsMs 2880931 Specdb::CMs 15824 Specdb::CMs 46929 Specdb::CMs 178446 Specdb::CMs 178447 Specdb::CMs 178448 Specdb::CMs 280896 HMDB0040723 Cottonseed Type 1 specific Gossypium 3633 251.25 375.0 127.5 mg/100 g Okra Type 1 specific Abelmoschus esculentus 455045 Soy bean Type 1 specific Glycine max 3847 Sunflower Type 1 specific Helianthus annuus 4232 1.0 1.0 1.0 mg/100 g Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). Amebicide 48 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anaphrodisiac 57 Angiotensin converting enzyme inhibitor 18 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti corpus-luteum 208 Anti estrogenic 272 A substance that diminishes the rate of a chemical reaction. Anti feedant 275 Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti implantation 364 Anti keratitic 379 Anti plasmodial 532 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti progesterone 545 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. Anti proliferant 547 Anti rabies 569 A substance that destroys or inhibits replication of viruses. Anti trypanosomic 669 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-encephalitic 255 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-fertility 276 Anti-flu 284 A substance that destroys or inhibits replication of viruses. Anti-herpetic 329 A substance that destroys or inhibits replication of viruses. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-spermatogenic 622 Anti-stomatitic 630 Anti-testosterone 642 A substance that diminishes the rate of a chemical reaction. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antibiotic 147 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Avicide 720 A substance used to destroy bird pests (class Aves). Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Contraceptive 830 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Fungicide 940 A substance used to destroy fungal pests. Hepatotoxic 984 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. Hypokalemic 1018 Immunostimulant 1032 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. Insectifuge 1041 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Interferonogenic 1049 Larvicide 1063 Libidolytic 1071 Mutagenic 1125 Nematistat 1143 Paralytic 1196 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Prostaglandigenic 1254 Prostaglandin synthesis inhibitor 1258 A substance that diminishes the rate of a chemical reaction. Spermicide 1322 Topoisomerase-II inhibitor 1366 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. Toxic 1371 A role played by the molecular entity or part thereof which causes the development of a pathological process. Tumorigenic 1388 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.