IMPPAT Phytochemical information: 
6-Methoxygossypol

6-Methoxygossypol
Summary

SMILES: O=Cc1c(O)c(OC)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/C31H32O8/c1-12(2)20-16-8-14(5)22(28(36)24(16)18(10-32)26(34)30(20)38)23-15(6)9-17-21(13(3)4)31(39-7)27(35)19(11-33)25(17)29(23)37/h8-13,34-38H,1-7H3
InChIKey: QSEHQWFPCMNMPH-UHFFFAOYSA-N
DeepSMILES: O=CccO)cOC))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; cOC
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,6-methoxy
External chemical identifiers:
CID:CID_3085061; ZINC:ZINC000085529975; SureChEMBL:SCHEMBL22700385
Chemical structure download


6-Methoxygossypol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 532.59
Log P RDKit 6.69
Topological polar surface area (Å2) RDKit 144.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


6-Methoxygossypol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.13649


6-Methoxygossypol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -4.40
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No