IMPPAT Phytochemical information: 
Hydroxygenistein
Hydroxygenistein
Summary

SMILES: OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(=O)c(c3O)c2ccc(cc2)O)C(C([C@@H]1O)O)O
InChI: InChI=1S/C21H20O11/c22-7-13-16(25)18(27)19(28)21(32-13)30-10-5-11(24)15-12(6-10)31-20(29)14(17(15)26)8-1-3-9(23)4-2-8/h1-6,13,16,18-19,21-28H,7H2/t13?,16-,18?,19?,21-/m1/s1
InChIKey: RLWUVXWTTCLDMO-ACTPKOLHSA-N
DeepSMILES: OCCO[C@@H]OcccO)ccc6)oc=O)cc6O))cccccc6))O))))))))))))))CC[C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1oc2cc(OC3CCCCO3)ccc2cc1-c1ccccc1
Scaffold Graph/Node level: OC1OC2CC(OC3CCCCO3)CCC2CC1C1CCCCC1
Scaffold Graph level: CC1CC2CC(CC3CCCCC3)CCC2CC1C1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavonoid O-glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
hydroxygenistein, hydroxygenisten, 2'-hydroxygenistin
External chemical identifiers:
CID:CID_129636354
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Hydroxygenistein
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.38
Log P RDKit -0.24
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
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
Hydroxygenistein
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
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 0.26
Hydroxygenistein
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.62
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No