ChemFOnt: Showing chemical card for p-Coumarylquinic acid (CFc000333549)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:44 UTC

Chemfont ID

CFc000333549

Molecule Identification

Common Name

p-Coumarylquinic acid

Definition

3-o-p-coumaroylquinic acid, also known as trans-5-O-(4-coumaroyl)-D-quinate, belongs to quinic acids and derivatives class of compounds. Those are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 3-o-p-coumaroylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3-o-p-coumaroylquinic acid can be found in a number of food items such as apple, carrot, corn, and sweet cherry, which makes 3-o-p-coumaroylquinic acid a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-p-Coumaroylquinate	Generator
1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9ci	HMDB
O-Coumaroylquinic acid	HMDB
p-Coumaroyl quinic acid	HMDB
trans-5-O-(4-Coumaroyl)-D-quinate	HMDB
trans-5-O-(4-Coumaroyl)-D-quinic acid	HMDB
2-Coumaroylquinic acid	HMDB

Chemical Formula

C₁₆H₁₈O₈

Average Molecular Weight

338.3093

Monoisotopic Molecular Weight

338.100167552

IUPAC Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O

InChI Identifier

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

InChI Key

BMRSEYFENKXDIS-QHAYPTCMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Coumaric acid ester
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Styrene
Phenol
Fatty acid ester
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Dicarboxylic acid or derivatives
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0029681)

Sweet cherry (FooDB: FOOD00145)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.92 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.035	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029681

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000240

KNApSAcK ID

C00052747

Chemspider ID

8121397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9945785

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for p-Coumarylquinic acid (CFc000333549)

MOL for CFc000333549 (p-Coumarylquinic acid)

3D MOL for CFc000333549 (p-Coumarylquinic acid)

3D SDF for CFc000333549 (p-Coumarylquinic acid)

3D-SDF for CFc000333549 (p-Coumarylquinic acid)

PDB for CFc000333549 (p-Coumarylquinic acid)

3D PDB for CFc000333549 (p-Coumarylquinic acid)

SMILES for CFc000333549 (p-Coumarylquinic acid)

INCHI for CFc000333549 (p-Coumarylquinic acid)

Structure for CFc000333549 (p-Coumarylquinic acid)

3D Structure for CFc000333549 (p-Coumarylquinic acid)