Showing Compound p-Coumaroylquinic acid (FDB000240)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:29 UTC

Update date

2020-09-17 15:41:35 UTC

Primary ID

FDB000240

Secondary Accession Numbers

FDB000866
FDB004557

Chemical Information

FooDB Name

p-Coumaroylquinic acid

Description

3-O-p-Coumaroylquinic acid 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. 3-p-coumaroylquinic acid can be found in a number of food items such as redcurrant, highbush blueberry, sweet cherry, and blackcurrant, which makes 3-p-coumaroylquinic acid a potential biomarker for the consumption of these food products. 3-O-p-Coumaroylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-O-p-Coumaroylquinic acid is found, on average, in the highest concentration within apples. 3-O-p-Coumaroylquinic acid has also been detected, but not quantified in, wild celeries. This could make 3-O-p-coumaroylquinic acid a potential biomarker for the consumption of these foods. 3-p-coumaroylquinic acid 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-p-coumaroylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa).

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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

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

Chemical Formula

C16H18O8

IUPAC name

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

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

Isomeric 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

Average Molecular Weight

338.3093

Monoisotopic Molecular Weight

338.100167552

Classification

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

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	p-Coumaroylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9532000000-2dc7a87d77bc1c19a7a3	Spectrum
Predicted GC-MS	p-Coumaroylquinic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-1240039000-8da17192a2ee13617f1f	Spectrum
Predicted GC-MS	p-Coumaroylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Negative	splash10-03di-0900000000-390db558397074a90625	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 30V, positive	splash10-0002-0900000000-fed2504c458f496f6118	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 15V, positive	splash10-0002-0900000000-ef57912ebc34156df393	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0002-0900000000-d3046051cdf55c7ab038	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0292-0914000000-8b2bc1f2847f25917bd0	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-009m-0936000000-4575bb1f18835ad1f7c5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0911000000-5088a3a2e259bc6b8801	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-1900000000-5bb81d1e3b6075572c1d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0988000000-68ceb4befe110f98609f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-1931000000-4f0bf43a1a7bcf541c7a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0900000000-debf809729d9088ae7a7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0946000000-d78957a03558e557100f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-46e6cf4cf6a54ee60670	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-4910000000-7fff648cbfff88afe159	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0902000000-600959b32de7a00f052c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xu-1900000000-89f3229591976d1bdbf9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-6b20c10637eed157aca2	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

466

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

P-COUMAROYL-QUINIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound p-Coumaroylquinic acid (FDB000240)

Structure for FDB000240 (p-Coumaroylquinic acid)