3-hydroxyphenylacetic acid (CHEBI:17445)

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CHEBI:17445 - 3-hydroxyphenylacetic acid

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ChEBI Name	3-hydroxyphenylacetic acid

ChEBI ID	CHEBI:17445

Definition	A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:39897, CHEBI:11833, CHEBI:1550, CHEBI:20076

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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Marvin 11300709453D

19 19 0 0 0 0 999 V2000

-1.0319 -1.7689 0.2529 C 0 0 0 0 0 0 0 0 0 3 0 0

-2.0007 -1.1015 1.0267 C 0 0 0 0 0 0 0 0 0 4 0 0

2.1189 1.3607 -0.3259 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9556 1.1535 -1.1619 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0785 0.3876 -0.4248 C 0 0 0 0 0 0 0 0 0 1 0 0

-0.0785 -1.0252 -0.4665 C 0 0 0 0 0 0 0 0 0 2 0 0

-2.0098 0.3053 1.0826 C 0 0 0 0 0 0 0 0 0 5 0 0

-1.0524 1.0431 0.3631 C 0 0 0 0 0 0 0 0 0 6 0 0

2.4868 2.4855 -0.0217 O 0 0 0 0 0 0 0 0 0 0 0 0

2.7574 0.4060 0.1089 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9991 -3.0218 0.1940 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.6999 -1.6306 1.5528 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5366 2.1033 -1.5083 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2589 0.6274 -2.0717 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6278 -1.5222 -1.0176 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7090 0.7929 1.6469 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0682 2.0646 0.4242 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4475 0.5215 0.6424 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3819 -3.4171 -0.2959 H 0 0 0 0 0 0 0 0 0 0 0 0

11 1 1 0 0 0 0

2 1 4 0 0 0 0

10 3 1 0 0 0 0

4 3 1 0 0 0 0

5 4 1 0 0 0 0

1 6 4 0 0 0 0

6 5 4 0 0 0 0

2 7 4 0 0 0 0

7 8 4 0 0 0 0

8 5 4 0 0 0 0

9 3 2 0 0 0 0

2 12 1 0 0 0 0

4 13 1 0 0 0 0

4 14 1 0 0 0 0

6 15 1 0 0 0 0

7 16 1 0 0 0 0

8 17 1 0 0 0 0

10 18 1 0 0 0 0

11 19 1 0 0 0 0

M END): 17 ms

reading 19 atoms

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19 atoms created

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Formula

C8H8O3

Net Charge

Average Mass

152.14732

Monoisotopic Mass

152.04734

InChI

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

InChIKey

FVMDYYGIDFPZAX-UHFFFAOYSA-N

SMILES

OC(=O)Cc1cccc(O)c1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	3-hydroxyphenylacetic acid (CHEBI:17445) has functional parent acetic acid (CHEBI:15366) 3-hydroxyphenylacetic acid (CHEBI:17445) has role human xenobiotic metabolite (CHEBI:76967) 3-hydroxyphenylacetic acid (CHEBI:17445) is a monocarboxylic acid (CHEBI:25384) 3-hydroxyphenylacetic acid (CHEBI:17445) is a phenols (CHEBI:33853) 3-hydroxyphenylacetic acid (CHEBI:17445) is conjugate acid of 3-hydroxyphenylacetate (CHEBI:58149)

Incoming	3-hydroxyphenylacetate (CHEBI:58149) is conjugate base of 3-hydroxyphenylacetic acid (CHEBI:17445)

IUPAC Name

(3-hydroxyphenyl)acetic acid

Synonyms	Sources
(m-hydroxyphenyl)acetic acid	ChemIDplus
3-hydroxybenzeneacetic acid	ChemIDplus
3-Hydroxyphenylacetic acid	KEGG COMPOUND
m-hydroxyphenylacetic acid	ChemIDplus

Manual Xrefs	Databases
3-HYDROXYPHENYLACETATE	MetaCyc
3HP	PDBeChem
C05593	KEGG COMPOUND
HMDB0000440	HMDB
US5639643	Patent
View more database links

Registry Numbers	Types	Sources
2086506	Reaxys Registry Number	Reaxys
621-37-4	CAS Registry Number	KEGG COMPOUND
621-37-4	CAS Registry Number	ChemIDplus

Citations

Wen KC, Chang CS, Chien YC, Wang HW, Wu WC, Wu CS, Chiang HM (2013)
Tyrosol and its analogues inhibit alpha-melanocyte-stimulating hormone induced melanogenesis.
International journal of molecular sciences 14, 23420-23440 [PubMed:24287915]
[show Abstract]

Henning SM, Wang P, Abgaryan N, Vicinanza R, de Oliveira DM, Zhang Y, Lee RP, Carpenter CL, Aronson WJ, Heber D (2013)
Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer.
Molecular nutrition & food research 57, 483-493 [PubMed:23319439]
[show Abstract]

Imolorhe IA, Cardona ST (2011)
3-Hydroxyphenylacetic acid induces the Burkholderia cenocepacia phenylacetic acid degradation pathway - toward understanding the contribution of aromatic catabolism to pathogenesis.
Frontiers in cellular and infection microbiology 1, 14 [PubMed:22919580]
[show Abstract]

Bock C, Ternes W (2010)
The phenolic acids from bacterial degradation of the mangiferin aglycone are quantified in the feces of pigs after oral ingestion of an extract of Cyclopia genistoides (honeybush tea).
Nutrition research (New York, N.Y.) 30, 348-357 [PubMed:20579527]
[show Abstract]

Lee CY, Sim SM, Cheng HM (2008)
Phenylacetic acids were detected in the plasma and urine of rats administered with low-dose mulberry leaf extract.
Nutrition research (New York, N.Y.) 28, 555-563 [PubMed:19083460]
[show Abstract]

Baba S, Furuta T, Horie M, Nakagawa H (1981)
Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans.
Journal of pharmaceutical sciences 70, 780-782 [PubMed:7264927]
[show Abstract]

Sandler M, Karoum F, Ruthven CR, Calne DB (1969)
m-Hydroxyphenylacetic acid formation from L-dopa in man: suppression by neomycin.
Science (New York, N.Y.) 166, 1417-1418 [PubMed:5350345]
[show Abstract]

Last Modified

09 December 2024

ChEBI

CHEBI:17445 - 3-hydroxyphenylacetic acid

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