IMPPAT Phytochemical information: 
27-p-Coumaroyloxy ursolic acid
27-p-Coumaroyloxy ursolic acid
Summary

SMILES: O=C(OCC12CC[C@@]3([C@H](C1=CCC1[C@@]2(C)CCC2[C@]1(C)CC[C@@H](C2(C)C)O)[C@@H](C)C(CC3)C)C(=O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C39H54O6/c1-24-15-20-38(34(43)44)21-22-39(23-45-32(42)14-9-26-7-10-27(40)11-8-26)28(33(38)25(24)2)12-13-30-36(5)18-17-31(41)35(3,4)29(36)16-19-37(30,39)6/h7-12,14,24-25,29-31,33,40-41H,13,15-23H2,1-6H3,(H,43,44)/b14-9+/t24?,25-,29?,30?,31-,33-,36-,37+,38-,39?/m0/s1
InChIKey: RZHJGXXCTIXCRI-VZJLLYDTSA-N
DeepSMILES: O=COCCCC[C@@][C@H]C6=CCC[C@@]%10C)CCC[C@]6C)CC[C@@H]C6C)C))O)))))))))))))[C@@H]C)CCC6))C))))C=O)O))))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC12CCC3CCCCC3C1=CCC1C3CCCCC3CCC12
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC12CCC3CCCCC3C1CCC1C3CCCCC3CCC12
Scaffold Graph level: CC(CCC1CCCCC1)CCC12CCC3CCCCC3C1CCC1C3CCCCC3CCC12
Functional groups: c/C=C/C(=O)OC; CC(=O)O; CC=C(C)C; cO; CO
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: Ursane and Taraxastane triterpenoids
Synonymous chemical names:
27-(p-coumaroyloxy) ursolic acid, ursolic acid, 27-p-coumaroyloxy
External chemical identifiers:
CID:CID_5459189
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
27-p-Coumaroyloxy ursolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 618.86
Log P RDKit 8.03
Topological polar surface area (Å2) RDKit 104.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 45
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 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
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 6
27-p-Coumaroyloxy ursolic acid
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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.18
27-p-Coumaroyloxy ursolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.22
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 Yes
P-glycoprotein substrate SwissADME Yes