IMPPAT Phytochemical information: 
Medicagenic acid
Medicagenic acid
Summary

SMILES: O[C@H]1C[C@@]2(C)[C@H]([C@]([C@H]1O)(C)C(=O)O)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C
InChI: InChI=1S/C30H46O6/c1-25(2)11-13-30(24(35)36)14-12-27(4)17(18(30)15-25)7-8-20-26(3)16-19(31)22(32)29(6,23(33)34)21(26)9-10-28(20,27)5/h7,18-22,31-32H,8-16H2,1-6H3,(H,33,34)(H,35,36)/t18-,19-,20+,21+,22-,26+,27+,28+,29-,30-/m0/s1
InChIKey: IDGXIXSKISLYAC-WNTKNEGGSA-N
DeepSMILES: O[C@H]C[C@@]C)[C@H][C@][C@H]6O))C)C=O)O)))CC[C@@][C@@H]6CC=C[C@@]6C)CC[C@@][C@H]6CCC)C)CC6)))))C=O)O))))))))))C
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CCCCC3C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Functional groups: CO; CC(=O)O; CC=C(C)C
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:
medicagenic acid
External chemical identifiers:
CID:CID_65048; ChEMBL:CHEMBL520726; ChEBI:CHEBI:167977; ZINC:ZINC000005663696; FDASRS:7X05537I17; SureChEMBL:SCHEMBL1050033; MolPort-039-337-172
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Medicagenic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 502.69
Log P RDKit 5.27
Topological polar surface area (Å2) RDKit 115.06
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 6
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
Medicagenic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
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 0.38255
Medicagenic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.27
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 Yes
Medicagenic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS