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Showing Compound Gossypol (FDB000742)

Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2019-11-26 02:55:19 UTC
Primary IDFDB000742
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGossypol
DescriptionGossypol, 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).
CAS Number303-45-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-GossypolHMDB
(+-)-GossypolHMDB
(+/-)-gossypolHMDB
(R)-(-)-GossypolHMDB
(R)-GossypolHMDB
Dipotassium salt, gossypolHMDB, MeSH
GossypolHMDB
Gossypol dipotassium saltHMDB, MeSH
Gossypol from cotton seedsHMDB
Gossypol sodium saltHMDB, MeSH
Gossypol, (+)-isomerHMDB, MeSH
Gossypol, (+-)-isomerHMDB, MeSH
Gossypol, (-)-isomerHMDB, MeSH
PogosinHMDB
Racemic-gossypolHMDB
Sodium salt, gossypolHMDB, MeSH
Tash 1HMDB
1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 9CIdb_source
Thespesindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP4.49ALOGPS
logP8.02ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity147.61 m³·mol⁻¹ChemAxon
Polarizability55.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H30O8
IUPAC name7-[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
InChI IdentifierInChI=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
InChI KeyQBKSWRVVCFFDOT-UHFFFAOYSA-N
Isomeric SMILESCC(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
Average Molecular Weight518.5544
Monoisotopic Molecular Weight518.194067936
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cadinane sesquiterpenoid
  • Sesquiterpenoid
  • 2-naphthol
  • 1-naphthol
  • Naphthalene
  • Aryl-aldehyde
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.49%; H 5.83%; O 24.68%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data375 (e 15850) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGossypol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0000690000-9df7326dd4ce60b1088cSpectrum
Predicted GC-MSGossypol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0000019000-f115e0a1dfade9af2f9bSpectrum
Predicted GC-MSGossypol, TMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, TMS_5_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, TMS_5_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, "(-)-Gossypol,4TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000190000-afd3b7806ba77c385fc92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1030970000-364f0989158c0f8675912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-5030940000-cb58d99e7632b192bd4d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-55621847e31c93e5127f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0070390000-dda96ff17c65a2928ec92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-1390300000-346fa91db1c09ffd5bec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-fb746155c08fc86203982021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0000950000-e97a10851934b81a75052021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000900000-5335728bfd70100979352021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-4887f71c2e78af6991412021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000390000-01a16a8a515827651a3e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0002910000-b9dfdfbb4b3c355cb8f02021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBGS60-C:BGS60-C
EAFUS IDNot Available
Dr. Duke IDGOSSYPOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 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).DUKE
amebicide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anaphrodisiacDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti corpus-luteumDUKE
anti encephalitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti feedantDUKE
anti fertilityDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti implantationDUKE
anti keratiticDUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antioxidant22586 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.DUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti progesterone49020 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.DUKE
anti proliferantDUKE
anti rabies22587 A substance that destroys or inhibits replication of viruses.DUKE
anti spermatogenicDUKE
anti stomatiticDUKE
anti testosterone35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
avicide33289 A substance used to destroy bird pests (class Aves).DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
contraceptive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypokalemicDUKE
immunostimulant50847 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.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
interferonogenicDUKE
larvicideDUKE
libidolyticDUKE
mutagenicDUKE
nematistatDUKE
paralyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandigenicDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
spermicideDUKE
topoisomerase-II inhibitor50750 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.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
tumorigenic50903 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.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).