ContaminantDB: 1-O-Caffeoylquinic acid

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

Record Information

Version

1.0

Creation Date

2016-05-25 21:50:53 UTC

Update Date

2016-11-09 01:17:56 UTC

Accession Number

CHEM024666

Identification

Common Name

1-O-Caffeoylquinic acid

Class

Small Molecule

Description

1-O-Caffeoylquinic acid is found in coffee and coffee products. 1-O-Caffeoylquinic acid is a constituent of coffee

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-O-Caffeoylquinate	Generator
1-(3,4-Dihydroxycinnamoyl)quinic acid	HMDB
1-Caffeoylquinic acid	HMDB
1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylate	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Mass

354.309 g/mol

Monoisotopic Mass

354.095 g/mol

CAS Registry Number

1241-87-8

IUPAC Name

1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylic acid

Traditional Name

1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylic acid

SMILES

OC1CC(CC(O)C1O)(OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2-

InChI Key

GWTUHAXUUFROTF-RQOWECAXSA-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

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	3.38 g/L	ALOGPS
logP	0.18	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	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	splash10-000f-9702000000-ebc50f242cde52b1c612	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-004i-7611039000-d35ccf21487d73faf0ca	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bti-0908000000-9866ebc23f957673d8b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g0-0902000000-96d0fc9dbc54b68dd5f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-07d9e80f514c6eff9378	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0519000000-0b9567ec172f62ce13f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ba-0922000000-3a7418ef1feecced9de1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-0900000000-cc70fcb57c2fbd8aff34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0419000000-282520a2e6da743e58e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-27ba18368b15c225c4c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002k-2900000000-c82499a88340eca01179	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0409000000-6a7b4699fd6e6e9c57fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-0933000000-93fe711f7608484f3b6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0019-0900000000-2895bc88d1ce61ee0d12	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

HMDB0030652

FooDB ID

FDB002560

Phenol Explorer ID

Not Available

KNApSAcK ID

C00055231

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

35013249

ChEBI ID

Not Available

PubChem Compound ID

131751066

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.

1-O-Caffeoylquinic acid (CHEM024666)

Structure for CHEM024666: 1-O-Caffeoylquinic acid