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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 Date2020-11-09 23:14:02 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
Data?1582752148
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
Download

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
ValueSource
(O-Hydroxyphenyl)acetic acidChEBI
2'-Hydroxyphenylacetic acidChEBI
2-Hydroxybenzeneacetic acidChEBI
2-Hydroxyphenylacetic acidChEBI
O-Hydroxyphenylacetic acidChEBI
(O-Hydroxyphenyl)acetateGenerator
2'-HydroxyphenylacetateGenerator
2-HydroxybenzeneacetateGenerator
2-HydroxyphenylacetateGenerator
O-HydroxyphenylacetateGenerator
Ortho-hydroxyphenylacetateGenerator
(2-Hydroxyphenyl)acetateHMDB
(2-Hydroxyphenyl)acetic acidHMDB
(O-Hydroxyphenyl)-acetateHMDB
(O-Hydroxyphenyl)-acetic acidHMDB
2-HPAAHMDB
HydroxyphenylacetateHMDB
Hydroxyphenylacetic acidHMDB
O-Hydroxyphenyl acetic acidHMDB
Ortho-hydroxyphenylacetic acidMeSH
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 effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

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
PropertyValueSource
Water Solubility6.38 g/LALOGPS
logP10(0.99) g/LALOGPS
logP10(1.31) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.18931661259
DarkChem[M-H]-127.64931661259
AllCCS[M+H]+132.14832859911
AllCCS[M-H]-128.56732859911
DeepCCS[M+H]+133.14630932474
DeepCCS[M-H]-129.87730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ortho-Hydroxyphenylacetic acidOC(=O)CC1=C(O)C=CC=C12955.5Standard polar33892256
ortho-Hydroxyphenylacetic acidOC(=O)CC1=C(O)C=CC=C11427.8Standard non polar33892256
ortho-Hydroxyphenylacetic acidOC(=O)CC1=C(O)C=CC=C11510.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ortho-Hydroxyphenylacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=CC=C1O1503.4Semi standard non polar33892256
ortho-Hydroxyphenylacetic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC=C1CC(=O)O1554.6Semi standard non polar33892256
ortho-Hydroxyphenylacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=CC=C1O[Si](C)(C)C1566.8Semi standard non polar33892256
ortho-Hydroxyphenylacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1O1740.7Semi standard non polar33892256
ortho-Hydroxyphenylacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC=C1CC(=O)O1790.5Semi standard non polar33892256
ortho-Hydroxyphenylacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1O[Si](C)(C)C(C)(C)C2044.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-ca3851c9928227913a972014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (2 TMS)splash10-0w29-1970000000-de8569a7d279b97680a42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - ortho-Hydroxyphenylacetic acid EI-B (Non-derivatized)splash10-0002-0960000000-1018d2254ff44190f41a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-ca3851c9928227913a972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized)splash10-0w29-1970000000-de8569a7d279b97680a42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-0a090cff04cd89d360222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-004i-6930000000-1903392fd44f061e93eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-0900000000-c0378212353f9c2470602012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-0900000000-2e1d10888e4b882683d42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-1900000000-87d962f7cd6aa06c48322012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0a4i-0900000000-e7c99cfd03a6c025cf2c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0900000000-e7c99cfd03a6c025cf2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-69f9fe8670d9a6ce3b782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-77bc386fb6ce14ec2dd12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOFsplash10-004i-9000000000-7fb7c81915195d1050782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-8f1c3458a31199029d712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOFsplash10-0a4i-5900000000-b7dfc901d3e6c4db398b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOFsplash10-004i-9100000000-e31e91ce81a098f179442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOFsplash10-0a4i-1900000000-e7bfeba3bf5179c0cbfb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-0c76ffcb76d341ed2f1d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOFsplash10-0a6r-7900000000-1b46df694de9c5dd84ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 35V, Negative-QTOFsplash10-0a4i-0900000000-81d25cd8f42ea4104dc92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOFsplash10-004i-9000000000-4ad240d4583d43a1ec3e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Negative-QTOFsplash10-0a4i-1900000000-bd8c8286e031da5cb96c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOFsplash10-0udi-8900000000-1c3e198c05d77bf0541f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-17130a549d9e41fac3f62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOFsplash10-000i-0900000000-6a2b0b911cb357174c272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOFsplash10-0a4i-1900000000-06436376438e44718bb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOFsplash10-056r-9300000000-19f4bd2f314d6c0b49bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOFsplash10-0zfr-0900000000-c00a2e1956529eb24b432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Negative-QTOFsplash10-0pc0-0900000000-a60511b0d006628958712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Negative-QTOFsplash10-0a59-4900000000-68a51d2b15b093ce15452017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.287 +/- 0.033 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.213 +/- 0.021 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.265 +/- 0.032 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.329 +/- 0.064 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.228 +/- 0.019 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.207 +/- 0.023 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.213 +/- 0.026 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified2.281 +/- 2.091 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.76 +/- 0.457 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.38-0.72 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified22.48 +/- 16.25 umol/mmol creatinineAdult (>18 years old)Not Specified
Normal		 details
UrineDetected and Quantified0.36-0.53 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 953 details
UrineDetected and Quantified<20 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0.594 +/- 0.372 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified0.966 +/- 1.338 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.189 +/- 0.966 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified2.0 (0.9-4.5) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified7.71 +/- 3.65 umol/mmol creatinineAdult (>18 years old)Not Specified
Normal		 details
UrineDetected and Quantified2.9 (1.4-3.7) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
UrineDetected and Quantified0.643 +/- 0.815 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.603 +/- 0.339 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.226 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified151.592 +/- 98.0886 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
UrineDetected and Quantified48.301 +/- 20.0636 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified97.346 +/- 59.448 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
UrineDetected and Quantified36.53 +/- 39.59 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
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