IMPPAT Phytochemical information: 
(4R)-2beta,3beta,23-trihydroxy-oleana-5,12-dien-28-oic acid

(4R)-2beta,3beta,23-trihydroxy-oleana-5,12-dien-28-oic acid
Summary

SMILES: OC[C@]1(C)[C@@H](O)[C@@H](O)C[C@@]2(C1=CC[C@@]1([C@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
InChI: InChI=1S/C30H46O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,9,19-20,22-23,31-33H,8,10-17H2,1-6H3,(H,34,35)/t19-,20-,22-,23-,26+,27-,28+,29+,30-/m0/s1
InChIKey: FJGGNIPUSLFYJJ-NIOQJKBVSA-N
DeepSMILES: OC[C@]C)[C@@H]O)[C@@H]O)C[C@@]C6=CC[C@@][C@H]6CC=C[C@@]6C)CC[C@@][C@H]6CCCC6))C)C))))C=O)O))))))))))C)))))C
Scaffold Graph/Node/Bond level: C1=C2CCCCC2C2CC=C3C4CCCCC4CCC3C2C1
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:
bassic acid
External chemical identifiers:
CID:CID_73242191; ZINC:ZINC000169636603
Chemical structure download


(4R)-2beta,3beta,23-trihydroxy-oleana-5,12-dien-28-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.69
Log P RDKit 5.1
Topological polar surface area (Å2) RDKit 97.99
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 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.83
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 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


(4R)-2beta,3beta,23-trihydroxy-oleana-5,12-dien-28-oic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41


(4R)-2beta,3beta,23-trihydroxy-oleana-5,12-dien-28-oic 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 -5.68
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