Bovine Metabolome Database: Showing metabocard for Ortho-Hydroxyphenylacetic acid (BMDB0000669)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:38 UTC

Update Date

2020-04-22 15:04:42 UTC

BMDB ID

BMDB0000669

Secondary Accession Numbers

BMDB00669

Metabolite Identification

Common Name

Ortho-Hydroxyphenylacetic acid

Description

Ortho-hydroxyphenylacetic acid, also known as (O-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Ortho-hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ortho-hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. Ortho-hydroxyphenylacetic acid has been found to be associated with several diseases known as eosinophilic esophagitis and irritable bowel syndrome; also ortho-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(O-Hydroxyphenyl)acetic acid	ChEBI
2'-Hydroxyphenylacetic acid	ChEBI
2-Hydroxybenzeneacetic acid	ChEBI
2-Hydroxyphenylacetic acid	ChEBI
O-Hydroxyphenylacetic acid	ChEBI
(O-Hydroxyphenyl)acetate	Generator
2'-Hydroxyphenylacetate	Generator
2-Hydroxybenzeneacetate	Generator
2-Hydroxyphenylacetate	Generator
O-Hydroxyphenylacetate	Generator
Ortho-hydroxyphenylacetate	Generator
(2-Hydroxyphenyl)acetate	HMDB
(2-Hydroxyphenyl)acetic acid	HMDB
(O-Hydroxyphenyl)-acetate	HMDB
(O-Hydroxyphenyl)-acetic acid	HMDB
2-HPAA	HMDB
Hydroxyphenylacetate	HMDB
Hydroxyphenylacetic acid	HMDB
O-Hydroxyphenyl acetic acid	HMDB
Ortho-hydroxyphenylacetic acid	MeSH

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

2-(2-hydroxyphenyl)acetic acid

Traditional Name

o-hydroxyphenylacetic acid

CAS Registry Number

614-75-5

SMILES

OC(=O)CC1=C(O)C=CC=C1

InChI Identifier

InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

InChI Key

CCVYRRGZDBSHFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetic acids

Direct Parent

2(hydroxyphenyl)acetic acids

Alternative Parents

Substituents

2(hydroxyphenyl)acetic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:28478 )
hydroxy monocarboxylic acid (CHEBI:28478 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	145 - 147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	44 mg/mL	Not Available
LogP	0.85	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.99	ALOGPS
logP	1.31	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.35 m³·mol⁻¹	ChemAxon
Polarizability	14.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28306241	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000669

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012331

KNApSAcK ID

Not Available

Chemspider ID

11476

KEGG Compound ID

C05852

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5639

PubChem Compound

11970

PDB ID

Not Available

ChEBI ID

28478

References

Synthesis Reference

Levine, Joseph; Eble, T. E.; Fischbach, Henry. Preparation of o-hydroxyphenylacetic acid. Journal of the American Chemical Society (1948), 70 1930.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Showing metabocard for Ortho-Hydroxyphenylacetic acid (BMDB0000669)

Structure for BMDB0000669 (Ortho-Hydroxyphenylacetic acid)