IMPPAT Phytochemical information: 
(2S,4aS,6aR,6aS,6bR,8aR,9S,10S,12aS,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
(2S,4aS,6aR,6aS,6bR,8aR,9S,10S,12aS,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Summary

SMILES: OC[C@@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@@](CC1)(C)C(=O)O)C)C)C
InChI: InChI=1S/C30H46O5/c1-25-11-12-26(2,24(34)35)16-19(25)18-15-20(32)23-27(3)9-8-22(33)28(4,17-31)21(27)7-10-30(23,6)29(18,5)14-13-25/h15,19,21-23,31,33H,7-14,16-17H2,1-6H3,(H,34,35)/t19-,21+,22-,23+,25+,26-,27-,28+,29+,30+/m0/s1
InChIKey: GSEPOEIKWTXTHS-WTMNEXLISA-N
DeepSMILES: OC[C@@]C)[C@@H]O)CC[C@][C@H]6CC[C@@][C@@H]6C=O)C=C[C@@]6C)CC[C@@][C@H]6C[C@@]CC6))C)C=O)O)))))C)))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C1C=C2C3CCCCC3CCC2C2CCC3CCCCC3C12
Scaffold Graph/Node level: OC1CC2C3CCCCC3CCC2C2CCC3CCCCC3C12
Scaffold Graph level: CC1CC2C3CCCCC3CCC2C2CCC3CCCCC3C12
Functional groups: CO; CC(=O)C=C(C)C; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
Glycyrrhetic acid, 24-hydroxy, 24 - hydroxy glycyrrhetic acid, 24-hydroxyliquiritic, 24-hydroxyglycyrrhetic-acid-methyl-ester, 24-hydroxyglycyrrhetic acid
External chemical identifiers:
CID:CID_101280182; ZINC:ZINC000033831738
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,4aS,6aR,6aS,6bR,8aR,9S,10S,12aS,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.69
Log P RDKit 5.39
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(2S,4aS,6aR,6aS,6bR,8aR,9S,10S,12aS,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
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 0.486732
(2S,4aS,6aR,6aS,6bR,8aR,9S,10S,12aS,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately 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 -5.85
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 No
P-glycoprotein substrate SwissADME Yes