IMPPAT Phytochemical information: 
Glycyrrhizic acid
Glycyrrhizic acid
Summary

SMILES: O[C@@H]1[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C
InChI: InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
InChIKey: LPLVUJXQOOQHMX-QWBHMCJMSA-N
DeepSMILES: O[C@@H][C@@H]O[C@@H]O[C@H]C=O)O))[C@H][C@@H][C@H]6O))O))O))))))[C@H]O[C@@H][C@H]6O))C=O)O))))O[C@H]CC[C@][C@H]C6C)C))CC[C@@][C@@H]6C=O)C=C[C@@]6C)CC[C@@][C@H]6C[C@]C)CC6))C=O)O)))))C)))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C1C=C2C3CCCCC3CCC2C2CCC3CC(OC4OCCCC4OC4CCCCO4)CCC3C12
Scaffold Graph/Node level: OC1CC2C3CCCCC3CCC2C2CCC3CC(OC4OCCCC4OC4CCCCO4)CCC3C12
Scaffold Graph level: CC1CC2C3CCCCC3CCC2C2CCC3CC(CC4CCCCC4CC4CCCCC4)CCC3C12
Functional groups: CC(=O)O; CC(C)=CC(C)=O; CO; CO[C@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
glycyrrhizin, glycyrrhizinic acid
External chemical identifiers:
CID:14982; ChEMBL:CHEMBL441687; ChEBI:15939; ZINC:ZINC000096015174; FDASRS:6FO62043WK; SureChEMBL:SCHEMBL17684; MolPort-006-113-280
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Glycyrrhizic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Glycyrrhizic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
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 0.17
Glycyrrhizic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.33
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Glycyrrhizic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000229277ENO2800
ENSP00000260010TLR2818
ENSP00000261465HSD11B1926
ENSP00000264867PPARGC1A800
ENSP00000282561GJA1800
ENSP00000316786HSD11B2883
ENSP00000324806GSK3B786
ENSP00000337459NOS1786
ENSP00000350941SRC800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.