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Showing metabocard for ortho-Hydroxyphenylacetic acid (HMDB0000669)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:03 UTC
HMDB IDHMDB0000669
Secondary Accession Numbers
  • HMDB00669
Metabolite Identification
Common Nameortho-Hydroxyphenylacetic acid
Descriptionortho-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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

      
  Mrv1652305271900242D          

 11 11  0  0  0  0            999 V2000
   -0.0430   -1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

HMDB0000669
     RDKit          3D
ortho-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8407   -1.0859   -0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.1613   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    0.0120   -0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.6509    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528    0.1973    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -0.5702    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -0.9881    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.6577   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.1085   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.5297   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279    1.2955   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.1365   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.7119    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.4723    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -0.8195    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595   -1.5844    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075   -0.9601   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130    0.3755   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    1.6100   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

      
  Mrv1652305271900242D          

 11 11  0  0  0  0            999 V2000
   -0.0430   -1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000669

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.606132955958135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.3788850306351

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.00071468776261

> <JCHEM_PKA_STRONGEST_BASIC>
-6.017511950103068

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
o-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

HMDB0000669
     RDKit          3D
ortho-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8407   -1.0859   -0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.1613   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    0.0120   -0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.6509    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528    0.1973    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -0.5702    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -0.9881    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.6577   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.1085   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.5297   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279    1.2955   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.1365   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.7119    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.4723    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -0.8195    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595   -1.5844    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075   -0.9601   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130    0.3755   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    1.6100   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.080  -3.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.414  -2.656   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.748  -3.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.748  -4.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.414  -5.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.080  -4.966   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.414  -1.116   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.253  -2.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.587  -3.426   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.587  -4.966   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.921  -2.656   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

COMPND    HMDB0000669
HETATM    1  O1  UNL     1       1.841  -1.086  -0.883  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.300  -0.161  -0.139  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.666   0.012  -0.123  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.337   0.651   0.648  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.053   0.197   0.395  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.757  -0.570   1.308  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.050  -0.988   1.065  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.702  -0.658  -0.105  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.011   0.108  -1.027  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.699   0.530  -0.774  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.028   1.296  -1.711  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.204  -0.136  -0.971  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.492   1.712   0.393  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.557   0.472   1.742  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.227  -0.820   2.221  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.560  -1.584   1.807  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.707  -0.960  -0.338  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.513   0.375  -1.951  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.912   1.610  -1.557  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

OC(=O)CC1=C(O)C=CC=C1
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INCHI for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(2-hydroxyphenyl)acetic acid
Traditional Nameo-hydroxyphenylacetic acid
CAS Registry Number614-75-5
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 KeyCCVYRRGZDBSHFU-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available131.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002096
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012331
KNApSAcK IDNot Available
Chemspider ID11476
KEGG Compound IDC05852
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5639
PubChem Compound11970
PDB IDNot Available
ChEBI ID28478
Food Biomarker OntologyNot Available
VMH ID2HYOXPLAC
MarkerDB IDMDB00000211
Good Scents IDrw1176931
References
Synthesis ReferenceLevine, 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
  1. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  2. Greenslade D, Havler ME, Humphrey MJ, Jordan BJ, Rance MJ: Species differences in the metabolism and excretion of fenclofenac. Xenobiotica. 1980 Oct;10(10):753-60. [PubMed:7456491 ]
  3. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [PubMed:357810 ]
  4. Langenbeck U, Behbehani A, Mench-Hoinowski A, Petersen M: Absence of a significant renal threshold for two aromatic acids in phenylketonuric children over two years of age. Eur J Pediatr. 1980 Aug;134(2):115-8. [PubMed:7439195 ]

Enzymes

Enzyme Details
1. 4-hydroxyphenylpyruvate dioxygenase
General function:
Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:
Key enzyme in the degradation of tyrosine.
Gene Name:
HPD
Uniprot ID:
P32754
Molecular weight:
40497.105
Reactions
Phenylpyruvic acid + Oxygen → ortho-Hydroxyphenylacetic acid + Carbon dioxidedetails