IMPPAT Phytochemical information: 
9-Hydroxy-6-oxo-6H-[1]benzofuro[3,2-c][1]benzopyran-3-yl beta-D-glucopyranoside
9-Hydroxy-6-oxo-6H-[1]benzofuro[3,2-c][1]benzopyran-3-yl beta-D-glucopyranoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)c2c3oc3c2ccc(c3)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H18O10/c22-7-14-16(24)17(25)18(26)21(31-14)28-9-2-4-11-13(6-9)30-20(27)15-10-3-1-8(23)5-12(10)29-19(11)15/h1-6,14,16-18,21-26H,7H2/t14-,16-,17+,18-,21-/m1/s1
InChIKey: JSKGNHCHUPJTOQ-YUZRNDJPSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)oc=O)cc6occ5cccc6)O)))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1oc2cc(OC3CCCCO3)ccc2c2oc3ccccc3c12
Scaffold Graph/Node level: OC1OC2CC(OC3CCCCO3)CCC2C2OC3CCCCC3C12
Scaffold Graph level: CC1CC2CC(CC3CCCCC3)CCC2C2CC3CCCCC3C12
Functional groups: CO; cO[C@@H](C)OC; coc; c=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Coumestans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Coumestan
Synonymous chemical names:
coumestrin(glycoside of coumestrol), coumestrin
External chemical identifiers:
CID:CID_45356238; ZINC:ZINC000059729540
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9-Hydroxy-6-oxo-6H-[1]benzofuro[3,2-c][1]benzopyran-3-yl beta-D-glucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 430.37
Log P RDKit 0.58
Topological polar surface area (Å2) RDKit 162.96
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
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 3
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 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
9-Hydroxy-6-oxo-6H-[1]benzofuro[3,2-c][1]benzopyran-3-yl beta-D-glucopyranoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.290513
9-Hydroxy-6-oxo-6H-[1]benzofuro[3,2-c][1]benzopyran-3-yl beta-D-glucopyranoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.24
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