IMPPAT Phytochemical information: 
Jacoumaric acid
Jacoumaric acid
Summary

SMILES: O=C(O[C@H]1[C@H](O)C[C@]2(C(C1(C)C)CC[C@@]1(C2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@H](C)CC1)C(=O)O)C)C)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C39H54O6/c1-23-16-19-39(34(43)44)21-20-37(6)27(32(39)24(23)2)13-14-30-36(5)22-28(41)33(35(3,4)29(36)17-18-38(30,37)7)45-31(42)15-10-25-8-11-26(40)12-9-25/h8-13,15,23-24,28-30,32-33,40-41H,14,16-22H2,1-7H3,(H,43,44)/b15-10+/t23-,24+,28-,29?,30?,32+,33+,36+,37-,38-,39+/m1/s1
InChIKey: FEVUQLLYZLSRLB-HEIPXHRQSA-N
DeepSMILES: O=CO[C@H][C@H]O)C[C@]CC6C)C))CC[C@@]C6CC=C[C@@]6C)CC[C@@][C@H]6[C@@H]C)[C@H]C)CC6)))))C=O)O))))))))))C)))))C))))))/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: c/C=C/C(=O)OC; CC(=O)O; CO; cO; 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: Ursane and Taraxastane triterpenoids
Synonymous chemical names:
jacoumaric acid
External chemical identifiers:
CID:CID_11700083; SureChEMBL:SCHEMBL13487369; MolPort-039-338-803
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Jacoumaric 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 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 5
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
Jacoumaric 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
Jacoumaric 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 -3.92
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