IMPPAT Phytochemical information: 
trans-5-O-(4-coumaroyl)-D-quinic acid
trans-5-O-(4-coumaroyl)-D-quinic acid
Summary

SMILES: O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1
InChIKey: BMRSEYFENKXDIS-OTCYKTEZSA-N
DeepSMILES: O=CO[C@@H]C[C@@]O)C[C@H][C@H]6O))O)))C=O)O))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCCC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1
Functional groups: c/C=C/C(=O)OC; CO; CC(=O)O; cO
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
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
3-o-p-coumaroyl-quinic-acid
External chemical identifiers:
CID:CID_6441280; ChEMBL:CHEMBL284243; ChEBI:CHEBI:15937; ZINC:ZINC000003804525; FDASRS:4C4BU5688G; SureChEMBL:SCHEMBL10307372; MolPort-001-740-213
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
trans-5-O-(4-coumaroyl)-D-quinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.31
Log P RDKit -0.35
Topological polar surface area (Å2) RDKit 144.52
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
trans-5-O-(4-coumaroyl)-D-quinic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
trans-5-O-(4-coumaroyl)-D-quinic 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.41
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 No