ContaminantDB: p-Coumaroylquinic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 20:45:10 UTC

Update Date

2016-11-09 01:17:36 UTC

Accession Number

CHEM022948

Identification

Common Name

p-Coumaroylquinic acid

Class

Small Molecule

Description

3-O-p-Coumaroylquinic acid is found in apple. 3-O-p-Coumaroylquinic acid is found in cider apples, tea, cacao etc

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

338.309 g/mol

Monoisotopic Mass

338.100 g/mol

CAS Registry Number

Not Available

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

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9532000000-2dc7a87d77bc1c19a7a3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-001i-1240039000-8da17192a2ee13617f1f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Negative	splash10-03di-0900000000-390db558397074a90625	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 30V, positive	splash10-0002-0900000000-fed2504c458f496f6118	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 15V, positive	splash10-0002-0900000000-ef57912ebc34156df393	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0002-0900000000-d3046051cdf55c7ab038	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0292-0914000000-8b2bc1f2847f25917bd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-009m-0936000000-4575bb1f18835ad1f7c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0911000000-5088a3a2e259bc6b8801	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-1900000000-5bb81d1e3b6075572c1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0988000000-68ceb4befe110f98609f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-1931000000-4f0bf43a1a7bcf541c7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0900000000-debf809729d9088ae7a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0946000000-d78957a03558e557100f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-46e6cf4cf6a54ee60670	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-4910000000-7fff648cbfff88afe159	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0902000000-600959b32de7a00f052c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xu-1900000000-89f3229591976d1bdbf9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-6b20c10637eed157aca2	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029681

FooDB ID

FDB000240

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052747

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8121397

ChEBI ID

Not Available

PubChem Compound ID

9945785

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

p-Coumaroylquinic acid (CHEM022948)

Structure for CHEM022948: p-Coumaroylquinic acid