IMPPAT Phytochemical information: 
p-Coumarylquinic acid

p-Coumarylquinic acid
Summary

SMILES: O[C@@H]1CC(O)(C[C@H](C1(O)C1Cc2c(O1)cccc2)O)C(=O)O
InChI: InChI=1S/C15H18O7/c16-10-6-14(20,13(18)19)7-11(17)15(10,21)12-5-8-3-1-2-4-9(8)22-12/h1-4,10-12,16-17,20-21H,5-7H2,(H,18,19)/t10-,11-,12?,14?,15?/m1/s1
InChIKey: VZJJJDVUISESPE-IQYJPVSDSA-N
DeepSMILES: O[C@@H]CCO)C[C@H]C6O)CCccO5)cccc6)))))))))O)))C=O)O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC(C1CCCCC1)O2
Scaffold Graph/Node level: C1CCC(C2CC3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3C2)CC1
Functional groups: CO; cOC; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Alcohols and polyols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
p-coumarylquinic acid
External chemical identifiers:
CID:CID_129663365
Chemical structure download


p-Coumarylquinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 310.3
Log P RDKit -0.95
Topological polar surface area (Å2) RDKit 127.45
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


p-Coumarylquinic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.476456


p-Coumarylquinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.75
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 No