IMPPAT Phytochemical information: 
Isovolubilin
Isovolubilin
Summary

SMILES: COc1cc2occ(c(=O)c2c(c1[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)O)c1ccc(cc1)OC
InChI: InChI=1S/C23H24O9/c1-10-18(24)21(27)22(28)23(32-10)17-14(30-3)8-15-16(20(17)26)19(25)13(9-31-15)11-4-6-12(29-2)7-5-11/h4-10,18,21-24,26-28H,1-3H3/t10?,18-,21-,22?,23-/m0/s1
InChIKey: MUVXOBQROCNFJU-OHDPDHAWSA-N
DeepSMILES: COcccoccc=O)c6cc%10[C@@H]OCC)[C@@H][C@@H]C6O))O))O))))))O))))cccccc6))OC
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2ccc(C3CCCCO3)cc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCC(C3CCCCO3)CC21
Scaffold Graph level: CC1C(C2CCCCC2)CCC2CCC(C3CCCCC3)CC21
Functional groups: cOC; coc; c=O; COC; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavonoid C-glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
Isovolubilin, isovolubilin, isovolubilin (6-c-α-l-rhamnopyranosylgenistein-4'-7-dimethylether)
External chemical identifiers:
CID:CID_44257334; ChEBI:CHEBI:167978
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isovolubilin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 444.44
Log P RDKit 1.73
Topological polar surface area (Å2) RDKit 138.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.22
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 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Isovolubilin
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47
Isovolubilin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -8.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes