1.02010-04-08 22:04:41 UTC2019-11-26 02:55:19 UTCFDB000742GossypolGossypol, 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, 9CIThespesinC30H30O8518.5544518.1940679367-[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(-)-gossypol303-45-7CC(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=C1CInChI=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,1-6H3QBKSWRVVCFFDOT-UHFFFAOYSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.SesquiterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsSesquiterpenoidsAromatic homopolycyclic compounds1-hydroxy-4-unsubstituted benzenoidsAryl-aldehydesHydrocarbon derivativesNaphthols and derivativesOrganic oxidesPolyolsVinylogous acids1-hydroxy-4-unsubstituted benzenoid1-naphthol2-naphtholAldehydeAromatic homopolycyclic compoundAryl-aldehydeBenzenoidCadinane sesquiterpenoidHydrocarbon derivativeNaphthaleneOrganic oxideOrganic oxygen compoundOrganooxygen compoundPolyolSesquiterpenoidVinylogous acidCadinane sesquiterpenoidsCadinane sesquiterpenoidsCadinanesTerpenoidspolyphenollogp4.49logs-5.13solubility3.85e-03 g/llogp8.02pka_strongest_acidic7.8pka_strongest_basic-6.1iupac7-[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-carbaldehydeaverage_mass518.5544mono_mass518.194067936smilesCC(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=C1CformulaC30H30O8inchiInChI=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,1-6H3inchikeyQBKSWRVVCFFDOT-UHFFFAOYSA-Npolar_surface_area155.52refractivity147.61polarizability55.95rotatable_bond_count4acceptor_count8donor_count6physiological_charge0formal_charge0Specdb::CMs15824Specdb::CMs46929Specdb::CMs178446Specdb::CMs178447Specdb::CMs178448Specdb::CMs280896Specdb::MsMs77448Specdb::MsMs77449Specdb::MsMs77450Specdb::MsMs137577Specdb::MsMs137578Specdb::MsMs137579Specdb::MsMs2798021Specdb::MsMs2798022Specdb::MsMs2798023Specdb::MsMs2880929Specdb::MsMs2880930Specdb::MsMs2880931CottonseedType 1specificGossypium3633251.25375.0127.5mg/100 gOkraType 1specificAbelmoschus esculentus455045Soy beanType 1specificGlycine max3847SunflowerType 1specificHelianthus annuus42321.01.01.0mg/100 galdose reductase inhibitor40An 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).amebicide48A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anaphrodisiac57angiotensin converting enzyme inhibitor18An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).anti bacterial145A substance that kills or slows the growth of bacteria.anti cancer159A substance that inhibits or prevents the proliferation of neoplasms.anti corpus-luteum208anti encephalitic255Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti estrogenic272A substance that diminishes the rate of a chemical reaction.anti feedant275anti fertility276anti flu284A substance that destroys or inhibits replication of viruses.anti herpetic329A substance that destroys or inhibits replication of viruses.anti HIV333A substance that destroys or inhibits replication of viruses.anti implantation364anti keratitic379anti malarial416A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti plasmodial532A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti progesterone545A 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 proliferant547anti rabies569A substance that destroys or inhibits replication of viruses.anti spermatogenic622anti stomatitic630anti testosterone642A substance that diminishes the rate of a chemical reaction.anti trypanosomic669A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti viral689A substance that destroys or inhibits replication of viruses.antibiotic147A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.antioxidant502A 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.antitumor672A substance that inhibits or prevents the proliferation of neoplasms.avicide720A substance used to destroy bird pests (class Aves).calcium antagonist748Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.contraceptive830Any substance introduced into a living organism with therapeutic or diagnostic purpose.cytotoxic859A role played by the molecular entity or part thereof which causes the development of a pathological process.fungicide940A substance used to destroy fungal pests.hepatotoxic984A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.hypokalemic1018immunostimulant1032A 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.insectifuge1041Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.interferonogenic1049larvicide1063libidolytic1071mutagenic1125nematistat1143paralytic1196pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.prostaglandigenic1254prostaglandin synthesis inhibitor1258A substance that diminishes the rate of a chemical reaction.spermicide1322topoisomerase-II inhibitor1366A 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.toxic1371A role played by the molecular entity or part thereof which causes the development of a pathological process.tumorigenic1388A 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.