General Information of MET (ID: META00295)
Name Ortho-Hydroxyphenylacetic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2-Hydroxyphenyl)acetate; (2-Hydroxyphenyl)acetic acid; (O-Hydroxyphenyl)-acetate; (O-Hydroxyphenyl)-acetic acid; (O-Hydroxyphenyl)acetate', 2'-Hydroxyphenylacetate, '2-Hydroxybenzeneacetate; (O-Hydroxyphenyl)acetic acid', 2'-Hydroxyphenylacetic acid, '2-Hydroxybenzeneacetic acid; 2-HPAA; 2-Hydroxyphenylacetate; 2-Hydroxyphenylacetic acid; Hydroxyphenylacetate; Hydroxyphenylacetic acid; O-Hydroxyphenyl acetic acid; O-Hydroxyphenylacetate; O-Hydroxyphenylacetic acid; Ortho-hydroxyphenylacetate; Ortho-hydroxyphenylacetic acid
Source Endogenous;Food;Microbial
Structure Type   Phenylacetic acids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Phenylacetic acids
PubChem CID
11970
HMDB ID
HMDB0000669
Formula
C8H8O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05852
ChEBI ID
28478
FooDB ID
FDB012331
ChemSpider ID
11476
METLIN ID
5639
Physicochemical Properties Molecular Weight 152.15 Topological Polar Surface Area 57.5
XlogP 0.9 Complexity 144
Heavy Atom Count 11 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
ortho-Hydroxyphenylacetic acid, also known as (o-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(Hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. ortho-Hydroxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). ortho-Hydroxyphenylacetic acid can be found in a number of food items such as natal plum, lemon verbena, half-highbush blueberry, and parsley, which makes ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these food products. ortho-Hydroxyphenylacetic acid can be found primarily in blood, feces, and urine. Moreover, ortho-hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases (EC 1.14.13.-) in the pathway styrene degradation (KEGG). ortho-Hydroxyphenylacetic acid is also a microbial metabolite.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change Ortho-Hydroxyphenylacetic acid concentration: decrease (FC = 0.78)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of ortho-Hydroxyphenylacetic acid levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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