ChemFOnt: Showing chemical card for 3-Hydroxyphenylacetic acid (CFc000000336)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:42 UTC

Chemfont ID

CFc000000336

Molecule Identification

Common Name

3-Hydroxyphenylacetic acid

Definition

3-Hydroxyphenylacetic acid is a rutin metabolite and an antioxidant. It has a protective biological activity in human. It is a substrate of enzyme 4-hydroxyphenylacetate 3-monooxygenase [EC 1.14.13.3] in the pathway tyrosine metabolism (KEGG, PMID 155437 ). 3-Hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. It is also a marker of gut Clostridium species. Higher levels are associated with higher levels of Clostridia (PMID: 27123458 ). 3-Hydroxyphenylacetic acid can also be found in Klebsiella (PMID: 1851804 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(m-Hydroxyphenyl)acetic acid	ChEBI
3-Hydroxybenzeneacetic acid	ChEBI
m-Hydroxyphenylacetic acid	ChEBI
(m-Hydroxyphenyl)acetate	Generator
3-Hydroxybenzeneacetate	Generator
m-Hydroxyphenylacetate	Generator
3-Hydroxyphenylacetate	Generator
(3-Hydroxy-phenyl)-acetate	HMDB
(3-Hydroxy-phenyl)-acetic acid	HMDB
3-Hydroxy-benzeneacetate	HMDB
3-Hydroxy-benzeneacetic acid	HMDB
Meta-hydroxyphenylacetic acid	HMDB
3'-Hydroxyphenylacetic acid	HMDB
2-(3-Hydroxyphenyl)acetic acid	HMDB
3-Hydroxyphenylacetic acid	KEGG

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

2-(3-hydroxyphenyl)acetic acid

Traditional Name

3-hydroxyphenylacetic acid

CAS Registry Number

621-37-4

SMILES

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

InChI Identifier

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

InChI Key

FVMDYYGIDFPZAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
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

monocarboxylic acid (CHEBI:17445 )
phenols (CHEBI:17445 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7107773)
Cerebrospinal Fluid (CSF) (PMID: 3958083)
Saliva (HMDB: HMDB0000440)
Cerebrospinal fluid (HMDB: HMDB0000440)

Excreta

Biofluid or Excreta

Urine (PMID: 15315398)
Feces (PMID: 24010549)

Cellular substructure

Cytoplasm (HMDB: HMDB0000440)

Source

Exogenous

Exogenous (HMDB: HMDB0000440)

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000440)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000440)

Tea

Tea products (HMDB: HMDB0000440)

Fat and oil

Olive oil (HMDB: HMDB0000440)

Fruit

Fruits (HMDB: HMDB0000440)

Vegetable

Vegetables (HMDB: HMDB0000440)

Legumes (HMDB: HMDB0000440)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000440)

Nut

Nuts (HMDB: HMDB0000440)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000440)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Microbe

Microbe (HMDB: HMDB0000440)
Klebsiella pneumoniae (HMDB: HMDB0000440)
Clostridium (HMDB: HMDB0000440)
Clostridium species (HMDB: HMDB0000440)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Phenylketonuria (MarkerDB: MDB00000161)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.98 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	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	14.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000440

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022047

KNApSAcK ID

Not Available

Chemspider ID

11624

KEGG Compound ID

C05593

BioCyc ID

3-HYDROXYPHENYLACETATE

BiGG ID

Not Available

Wikipedia Link

4-Hydroxyphenylacetic acid

METLIN ID

5429

PubChem Compound

12122

PDB ID

Not Available

ChEBI ID

17445

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Staudenmaier, Horst Ralf; Hauer, Bernhard; Ladner, Wolfgang; Mueller, Ursula; Pressler, Uwe; Meyer, Joachim. Fermentative manufacture of 3-hydroxyphenylacetic acid. Ger. Offen. (1993), 6 pp.

Showing chemical card for 3-Hydroxyphenylacetic acid (CFc000000336)

MOL for CFc000000336 (3-Hydroxyphenylacetic acid)

3D MOL for CFc000000336 (3-Hydroxyphenylacetic acid)

3D SDF for CFc000000336 (3-Hydroxyphenylacetic acid)

3D-SDF for CFc000000336 (3-Hydroxyphenylacetic acid)

PDB for CFc000000336 (3-Hydroxyphenylacetic acid)

3D PDB for CFc000000336 (3-Hydroxyphenylacetic acid)

SMILES for CFc000000336 (3-Hydroxyphenylacetic acid)

INCHI for CFc000000336 (3-Hydroxyphenylacetic acid)

Structure for CFc000000336 (3-Hydroxyphenylacetic acid)

3D Structure for CFc000000336 (3-Hydroxyphenylacetic acid)