IMPPAT Phytochemical information: 
Glabridin
Glabridin
Summary

SMILES: Oc1ccc(c(c1)O)[C@@H]1COc2c(C1)ccc1c2C=CC(O1)(C)C
InChI: InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
InChIKey: LBQIJVLKGVZRIW-ZDUSSCGKSA-N
DeepSMILES: Occcccc6)O))[C@@H]COccC6)cccc6C=CCO6)C)C
Scaffold Graph/Node/Bond level: C1=Cc2c(ccc3c2OCC(c2ccccc2)C3)OC1
Scaffold Graph/Node level: C1CCC(C2COC3C(CCC4OCCCC43)C2)CC1
Scaffold Graph level: C1CCC(C2CCC3C(CCC4CCCCC43)C2)CC1
Functional groups: cC=CC; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Pyranoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavanones
Synonymous chemical names:
glabridin
External chemical identifiers:
CID:124052; ChEMBL:CHEMBL480477; ChEBI:5369; ZINC:ZINC000004098719; FDASRS:HOC5567T41; SureChEMBL:SCHEMBL114869; MolPort-005-934-878
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Glabridin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.38
Log P RDKit 4
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Glabridin
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 Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.8322
Glabridin
ADMET 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.52
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
Glabridin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000237014TTR800
ENSP00000263321TYR859
ENSP00000264832ICAM1800
ENSP00000304811UGT2B7755
ENSP00000304845UGT1A1755
ENSP00000337459NOS1786
ENSP00000341045UGT2B15755
ENSP00000343838UGT1A10755
ENSP00000346768UGT1A9742
ENSP00000362549UGT1A8742
ENSP00000418532UGT1A3784
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.