IMPPAT Phytochemical information: 
Gossypol

Gossypol
Summary

SMILES: O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C
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
InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N
DeepSMILES: O=CccO)cO)ccc6cO)ccc6)C))ccC)cccc6O))cC=O))ccc6CC)C)))O))O))))))))))))CC)C
Scaffold Graph/Node/Bond level: c1ccc2cc(-c3ccc4ccccc4c3)ccc2c1
Scaffold Graph/Node level: C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1
Scaffold Graph level: C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1
Functional groups: cC=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Cadinane sesquiterpenoids
Synonymous chemical names:
(+)-gossypol, gossoypol, gossypol, gossypol,(-)-
External chemical identifiers:
CID:3503; ChEMBL:CHEMBL51483; ZINC:ZINC000003775575; FDASRS:XNA7DR63CQ; SureChEMBL:SCHEMBL3939; MolPort-003-665-510
Chemical structure download


Gossypol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Gossypol
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1312


Gossypol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.54
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Gossypol
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216714APEX1800
ENSP00000260433CYP19A1800
ENSP00000276431TNFRSF10B816
ENSP00000283916TMPRSS11D786
ENSP00000302564BCL2L1819
ENSP00000311032CASP3738
ENSP00000329623BCL2735
ENSP00000330237CASP9732
ENSP00000350941SRC863
ENSP00000358022MCL1933
ENSP00000358327CASP7700
ENSP00000398495DIABLO824
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.