IMPPAT Phytochemical information: 
3-p-Coumaroylrotundic acid
3-p-Coumaroylrotundic acid
Summary

SMILES: OC[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@@H](CC1)C)C(=O)O)C)C)OC(=O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C39H54O7/c1-24-15-20-39(33(43)44)22-21-36(4)27(32(39)38(24,6)45)12-13-29-34(2)18-17-30(35(3,23-40)28(34)16-19-37(29,36)5)46-31(42)14-9-25-7-10-26(41)11-8-25/h7-12,14,24,28-30,32,40-41,45H,13,15-23H2,1-6H3,(H,43,44)/b14-9+/t24-,28-,29-,30+,32-,34+,35+,36-,37-,38-,39+/m1/s1
InChIKey: WSWPNGAODCKAHB-IFRVZBAOSA-N
DeepSMILES: OC[C@]C)[C@H]CC[C@][C@H]6CC[C@@][C@@H]6CC=C[C@@]6C)CC[C@@][C@H]6[C@]C)O)[C@@H]CC6))C))))C=O)O))))))))))C)))))C))))OC=O)/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2C(CCC3C4CCC5CCCCC5C4=CCC23)C1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2C(CCC3C2CCC2C4CCCCC4CCC23)C1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2C(CCC3C2CCC2C4CCCCC4CCC23)C1
Functional groups: CO; c/C=C/C(=O)OC; cO; CC=C(C)C; CC(=O)O
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:
3-o-trans-p-coumaroyl-rotundic-acid
External chemical identifiers:
CID:CID_44584641; ChEMBL:CHEMBL506962; ZINC:ZINC000049898250
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-p-Coumaroylrotundic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 634.85
Log P RDKit 7.15
Topological polar surface area (Å2) RDKit 124.29
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.28
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
3-p-Coumaroylrotundic acid
Drug-likeness properties
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 4
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 0.154106
3-p-Coumaroylrotundic 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 -5.20
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