ContaminantDB: Hydroxycaffeic acid

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

Record Information

Version

1.0

Creation Date

2016-05-25 20:45:34 UTC

Update Date

2016-11-09 01:17:36 UTC

Accession Number

CHEM022963

Identification

Common Name

Hydroxycaffeic acid

Class

Small Molecule

Description

Hydroxycaffeic acid, also known as hydroxycaffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Hydroxycaffeic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Hydroxycaffeic acid can be found in olive, which makes hydroxycaffeic acid a potential biomarker for the consumption of this food product.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(2,3,4-Trihydroxyphenyl)prop-2-enoate	Generator
Hydroxycaffeate	Generator

Chemical Formula

C₉H₈O₅

Average Molecular Mass

196.157 g/mol

Monoisotopic Mass

196.037 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2E)-3-(2,3,4-trihydroxyphenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(2,3,4-trihydroxyphenyl)prop-2-enoic acid

SMILES

OC(=O)\C=C\C1=C(O)C(O)=C(O)C=C1

InChI Identifier

InChI=1S/C9H8O5/c10-6-3-1-5(2-4-7(11)12)8(13)9(6)14/h1-4,10,13-14H,(H,11,12)/b4-2+

InChI Key

RHGWNBSOWGUGPA-DUXPYHPUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
5-unsubstituted pyrrogallol
Benzenetriol
Pyrogallol derivative
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
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	1.43 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.23	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49 m³·mol⁻¹	ChemAxon
Polarizability	18.05 Å³	ChemAxon
Number of Rings	1	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	splash10-0ufs-1900000000-f90579cd732eaf93951c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0i7i-3028900000-2e7d7d73b43bed14df37	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-002b-0900000000-e26fc3bbcdced026f8c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ug1-1900000000-bfe1dd5222889b90412c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9400000000-d36e8a0e6a200edd32e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-79a7fe792b5d5deda87b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1900000000-94666712b50cc3055c89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9800000000-650695baff2f8917f304	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004s-0900000000-94bdd29075c7c04c4953	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-1e5102a76e97317038a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9500000000-81cb720aabeaa5eabdb6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-0900000000-005c058c52ce19259351	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-580beef394131ff38607	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-5900000000-334bc5ff5e2e30d11990	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

HMDB0126031

FooDB ID

FDB000262

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

21889163

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis)

Hydroxycaffeic acid (CHEM022963)

Structure for CHEM022963: Hydroxycaffeic acid