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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:18:03 UTC
Update Date2022-03-07 02:56:42 UTC
HMDB IDHMDB0040723
Secondary Accession Numbers
  • HMDB40723
Metabolite Identification
Common Name(-)-Gossypol
Description(-)-Gossypol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (-)-gossypol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-Gossypol.
Structure
Data?1563863581
Synonyms
ValueSource
(+)-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
Chemical FormulaC30H30O8
Average Molecular Weight518.5544
Monoisotopic Molecular Weight518.194067936
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
Traditional Name(-)-gossypol
CAS Registry Number90141-22-3
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
InChI Identifier
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
InChI KeyQBKSWRVVCFFDOT-UHFFFAOYSA-N
Chemical Taxonomy
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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 183 °CNot Available
Boiling Point707.89 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.5e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.419 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+217.56331661259
DarkChem[M-H]-218.18931661259
DeepCCS[M+H]+222.07830932474
DeepCCS[M-H]-220.1830932474
DeepCCS[M-2H]-253.4230932474
DeepCCS[M+Na]+227.930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-GossypolCC(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=C1C5334.7Standard polar33892256
(-)-GossypolCC(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=C1C3432.0Standard non polar33892256
(-)-GossypolCC(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=C1C4402.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Gossypol,1TMS,isomer #1CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C4173.3Semi standard non polar33892256
(-)-Gossypol,1TMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O4168.2Semi standard non polar33892256
(-)-Gossypol,1TMS,isomer #3CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O4157.7Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #1CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C4029.6Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C4055.3Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #3CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C4053.6Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #4CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C4030.4Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #5CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C4065.6Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #6CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O4060.4Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #7CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O4097.9Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #8CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O4081.5Semi standard non polar33892256
(-)-Gossypol,2TMS,isomer #9CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O4019.5Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #1CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C4006.4Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #10CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O3998.9Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C3947.7Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #3CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C3949.2Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #4CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3988.3Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #5CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3983.2Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #6CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C3977.6Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #7CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C4029.7Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #8CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C4019.6Semi standard non polar33892256
(-)-Gossypol,3TMS,isomer #9CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O4029.2Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #1CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3967.9Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #2CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C3944.0Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #3CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3962.7Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #4CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C3940.3Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #5CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3950.1Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #6CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3949.3Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #7CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3968.8Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #8CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3964.0Semi standard non polar33892256
(-)-Gossypol,4TMS,isomer #9CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O3997.3Semi standard non polar33892256
(-)-Gossypol,5TMS,isomer #1CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3965.0Semi standard non polar33892256
(-)-Gossypol,5TMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3982.3Semi standard non polar33892256
(-)-Gossypol,5TMS,isomer #3CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C3977.1Semi standard non polar33892256
(-)-Gossypol,1TBDMS,isomer #1CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4419.6Semi standard non polar33892256
(-)-Gossypol,1TBDMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4384.4Semi standard non polar33892256
(-)-Gossypol,1TBDMS,isomer #3CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O4384.4Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #1CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4495.8Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4528.0Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #3CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4501.7Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #4CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4498.9Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #5CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4539.9Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #6CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4511.5Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #7CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4543.1Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #8CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4558.7Semi standard non polar33892256
(-)-Gossypol,2TBDMS,isomer #9CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O4477.8Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #1CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4679.3Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #10CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4684.7Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #2CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4593.6Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #3CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4612.1Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #4CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4651.8Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #5CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4657.6Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #6CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4645.2Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #7CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4684.7Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #8CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C4695.8Semi standard non polar33892256
(-)-Gossypol,3TBDMS,isomer #9CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O4724.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0000690000-9df7326dd4ce60b1088c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS (2 TMS) - 70eV, Positivesplash10-0002-0000019000-f115e0a1dfade9af2f9b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_4_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_5_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_5_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Gossypol GC-MS ("(-)-Gossypol,4TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Positive-QTOFsplash10-014i-0000190000-afd3b7806ba77c385fc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Positive-QTOFsplash10-016r-1030970000-364f0989158c0f8675912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Positive-QTOFsplash10-0pb9-5030940000-cb58d99e7632b192bd4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Negative-QTOFsplash10-014i-0000090000-55621847e31c93e5127f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Negative-QTOFsplash10-066r-0070390000-dda96ff17c65a2928ec92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Negative-QTOFsplash10-0a4u-1390300000-346fa91db1c09ffd5bec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Negative-QTOFsplash10-014i-0000090000-fb746155c08fc86203982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Negative-QTOFsplash10-014r-0000950000-e97a10851934b81a75052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Negative-QTOFsplash10-03di-0000900000-5335728bfd70100979352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Positive-QTOFsplash10-014i-0000090000-4887f71c2e78af6991412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Positive-QTOFsplash10-014i-0000390000-01a16a8a515827651a3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Positive-QTOFsplash10-03di-0002910000-b9dfdfbb4b3c355cb8f02021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13044
Phenol Explorer Compound IDNot Available
FooDB IDFDB000742
KNApSAcK IDC00003136
Chemspider ID3383
KEGG Compound IDC07667
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3503
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1526291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meng Y, Tang W, Dai Y, Wu X, Liu M, Ji Q, Ji M, Pienta K, Lawrence T, Xu L: Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa. Mol Cancer Ther. 2008 Jul;7(7):2192-202. doi: 10.1158/1535-7163.MCT-08-0333. [PubMed:18645028 ]
  2. Zhang XQ, Huang XF, Mu SJ, An QX, Xia AJ, Chen R, Wu DC: Inhibition of proliferation of prostate cancer cell line, PC-3, in vitro and in vivo using (-)-gossypol. Asian J Androl. 2010 May;12(3):390-9. doi: 10.1038/aja.2009.87. Epub 2010 Jan 18. [PubMed:20081872 ]
  3. Zhang Y, Kulp SK, Sugimoto Y, Brueggemeier RW, Lin YC: The (-)-enantiomer of gossypol inhibits proliferation of stromal cells derived from human breast adipose tissues by enhancing transforming growth factor beta1 production. Int J Oncol. 1998 Dec;13(6):1291-7. [PubMed:9824647 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.