IMPPAT Phytochemical information: 
Villosinol
Villosinol
Summary

SMILES: COc1cc2OCC3C(c2cc1OC)(O)C(=O)c1c(O3)c2CC(Oc2cc1O)C(=C)C
InChI: InChI=1S/C23H22O8/c1-10(2)14-5-11-15(30-14)7-13(24)20-21(11)31-19-9-29-16-8-18(28-4)17(27-3)6-12(16)23(19,26)22(20)25/h6-8,14,19,24,26H,1,5,9H2,2-4H3
InChIKey: JCJPVNDLAAXNEX-UHFFFAOYSA-N
DeepSMILES: COcccOCCCc6cc%10OC)))))O)C=O)ccO6)cCCOc5cc9O)))))C=C)C
Scaffold Graph/Node/Bond level: O=C1c2ccc3c(c2OC2COc4ccccc4C12)CCO3
Scaffold Graph/Node level: OC1C2CCC3OCCC3C2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCC3CCCC3C2CC2CCC3CCCCC3C21
Functional groups: cOC; CO; cC(=O)C; cO; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Rotenoids
Synonymous chemical names:
villosinol, villarinol, Villosinol
External chemical identifiers:
CID:CID_14704458; MolPort-019-937-107
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Villosinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 426.42
Log P RDKit 2.51
Topological polar surface area (Å2) RDKit 103.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Villosinol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.72
Villosinol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No