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
Synonyms
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
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).