IMPPAT Phytochemical information: 
Oleagenin
Oleagenin
Summary

SMILES: O[C@H]1CC[C@]2([C@@H](C1)CC[C@@]13[C@@H]2CC[C@](C3=O)(C)[C@H](CC1)C1=CC(=O)OC1)C
InChI: InChI=1S/C23H32O4/c1-21-7-4-16(24)12-15(21)3-9-23-10-5-17(14-11-19(25)27-13-14)22(2,20(23)26)8-6-18(21)23/h11,15-18,24H,3-10,12-13H2,1-2H3/t15-,16+,17-,18-,21+,22-,23+/m1/s1
InChIKey: WLKITKZNBMSWFH-PWJYONHCSA-N
DeepSMILES: O[C@H]CC[C@][C@@H]C6)CC[C@][C@@H]6CC[C@]C6=O))C)[C@H]CC8))C=CC=O)OC5))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC34CCC5CCCCC5C3CCC2C4=O)CO1
Scaffold Graph/Node level: OC1CC(C2CCC34CCC5CCCCC5C3CCC2C4O)CO1
Scaffold Graph level: CC1CCC(C2CCC34CCC5CCCCC5C3CCC2C4C)C1
Functional groups: CO; CC(=O)C; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Dihydrofurans
ClassyFire Subclass: Furanones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cardenolides
Synonymous chemical names:
oleagenin, Oleagenin
External chemical identifiers:
CID:CID_101967000
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Oleagenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.51
Log P RDKit 3.81
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
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
Oleagenin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.71
Oleagenin
ADME 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 -6.32
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