IMPPAT Phytochemical information: 
Medicagenic acid 3-O-beta-D-glucopyranoside
Medicagenic acid 3-O-beta-D-glucopyranoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3(C(C2(C)C(=O)O)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C36H56O11/c1-31(2)11-13-36(30(44)45)14-12-33(4)18(19(36)15-31)7-8-22-32(3)16-20(38)27(35(6,29(42)43)23(32)9-10-34(22,33)5)47-28-26(41)25(40)24(39)21(17-37)46-28/h7,19-28,37-41H,8-17H2,1-6H3,(H,42,43)(H,44,45)/t19-,20+,21-,22-,23?,24-,25+,26-,27+,28+,32-,33-,34-,35?,36+/m1/s1
InChIKey: XCHARIIIZLLEBL-GHKSOYFMSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H][C@@H]O)C[C@]CC6C)C=O)O)))CC[C@@][C@@H]6CC=C[C@@]6C)CC[C@@][C@@H]6CCC)C)CC6)))))C=O)O))))))))))C)))))C))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CC(OC4CCCCO4)CCC3C2C1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(CCC4C3CCC3C5CCCCC5CCC34)C2)OC1
Scaffold Graph level: C1CCC(CC2CCC3C(CCC4C3CCC3C5CCCCC5CCC34)C2)CC1
Functional groups: CO; CO[C@@H](C)OC; 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: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
medicagenic acid-3-o-glucopyranoside, Medicagenic acid-3-O-glucopyranoside, medicagenic acid-3-o-beta-d-glucopyranoside, medicagenic acid 3-o-β-d-glucopyranoside
External chemical identifiers:
CID:CID_162084
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Medicagenic acid 3-O-beta-D-glucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 664.83
Log P RDKit 3.09
Topological polar surface area (Å2) RDKit 194.21
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.89
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Medicagenic acid 3-O-beta-D-glucopyranoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17
Medicagenic acid 3-O-beta-D-glucopyranoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.79
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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