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Showing metabocard for 3-Hydroxyphenylacetic acid (HMDB0000440)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:52 UTC
HMDB IDHMDB0000440
Secondary Accession Numbers
  • HMDB00440
Metabolite Identification
Common Name3-Hydroxyphenylacetic acid
Description3-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
Data?1676999690
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000440 (3-Hydroxyphenylacetic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    1.6500   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000440 (3-Hydroxyphenylacetic acid)

HMDB0000440
     RDKit          3D
3-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8465    1.6047    1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    0.6502    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    0.5211    0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -0.3217   -0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -0.1082   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    0.6857   -1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380    0.8583   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.2457   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -0.5478    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.1529    1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.7281    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452    0.0522    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687   -1.3372    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -0.3411   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.1765   -1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    1.4756   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    0.3712   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.7365    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1915   -1.3677    1.4824 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  1  0
  9 11  2  0
 11  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
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for HMDB0000440 (3-Hydroxyphenylacetic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    1.6500   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000440

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.777919898848198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.470982050154852

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9988857987295043

> <JCHEM_PKA_STRONGEST_BASIC>
-5.965684195856604

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.346500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000440 (3-Hydroxyphenylacetic acid)

HMDB0000440
     RDKit          3D
3-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8465    1.6047    1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    0.6502    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    0.5211    0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -0.3217   -0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -0.1082   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    0.6857   -1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380    0.8583   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.2457   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -0.5478    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.1529    1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.7281    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452    0.0522    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687   -1.3372    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -0.3411   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.1765   -1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    1.4756   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    0.3712   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.7365    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1915   -1.3677    1.4824 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  1  0
  9 11  2  0
 11  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
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for HMDB0000440 (3-Hydroxyphenylacetic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       3.080  -3.226   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   3.704   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   1.394   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.747  -0.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747   1.394   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -2.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -2.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -3.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   2.164   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    6    7                                                  
CONECT    5    4   11                                                       
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    1    6   10                                                  
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000440 (3-Hydroxyphenylacetic acid)

COMPND    HMDB0000440
HETATM    1  O1  UNL     1       1.846   1.605   1.289  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.382   0.650   0.669  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.759   0.521   0.796  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.670  -0.322  -0.165  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.224  -0.108  -0.240  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.390   0.686  -1.201  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.738   0.858  -1.236  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.558   0.246  -0.310  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.950  -0.548   0.651  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.803  -1.153   1.572  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.579  -0.728   0.693  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.345   0.052   0.135  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.869  -1.337   0.274  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.133  -0.341  -1.179  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.227   1.177  -1.937  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.232   1.476  -1.980  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.637   0.371  -0.321  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.378  -1.736   2.282  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.191  -1.368   1.482  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   11
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   11   11
CONECT   10   18
CONECT   11   19
END
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SMILES for HMDB0000440 (3-Hydroxyphenylacetic acid)

OC(=O)CC1=CC(O)=CC=C1
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INCHI for HMDB0000440 (3-Hydroxyphenylacetic acid)

InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(m-Hydroxyphenyl)acetic acidChEBI
3-Hydroxybenzeneacetic acidChEBI
m-Hydroxyphenylacetic acidChEBI
(m-Hydroxyphenyl)acetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
3-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
Meta-hydroxyphenylacetic acidHMDB
3'-Hydroxyphenylacetic acidHMDB
2-(3-Hydroxyphenyl)acetic acidHMDB
3-Hydroxyphenylacetic acidKEGG
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(3-hydroxyphenyl)acetic acid
Traditional Name3-hydroxyphenylacetic acid
CAS Registry Number621-37-4
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 KeyFVMDYYGIDFPZAX-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.98 g/LALOGPS
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
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
Polarizability14.78 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]+134.04931661259
DarkChem[M-H]-128.86431661259
AllCCS[M+H]+131.91232859911
AllCCS[M-H]-128.55132859911
DeepCCS[M+H]+131.35330932474
DeepCCS[M-H]-128.08930932474
DeepCCS[M-2H]-165.19930932474
DeepCCS[M+Na]+140.62130932474
AllCCS[M+H]+131.932859911
AllCCS[M+H-H2O]+127.432859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.432859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-129.832859911
AllCCS[M+HCOO]-131.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.24 minutes32390414
Predicted by Siyang on May 30, 20229.7736 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.72 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid56.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1161.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid323.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid109.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid189.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid108.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid374.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid324.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)130.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid764.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid315.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid988.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid222.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid280.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate475.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA254.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water199.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyphenylacetic acidOC(=O)CC1=CC(O)=CC=C13096.4Standard polar33892256
3-Hydroxyphenylacetic acidOC(=O)CC1=CC(O)=CC=C11524.4Standard non polar33892256
3-Hydroxyphenylacetic acidOC(=O)CC1=CC(O)=CC=C11576.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyphenylacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=CC(O)=C11645.6Semi standard non polar33892256
3-Hydroxyphenylacetic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(CC(=O)O)=C11635.1Semi standard non polar33892256
3-Hydroxyphenylacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=CC(O[Si](C)(C)C)=C11623.3Semi standard non polar33892256
3-Hydroxyphenylacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(O)=C11865.5Semi standard non polar33892256
3-Hydroxyphenylacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(CC(=O)O)=C11861.2Semi standard non polar33892256
3-Hydroxyphenylacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12069.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodDetected and Quantified0.466 +/- 0.192 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.129 +/- 0.031 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.677 +/- 0.238 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.583 +/- 0.161 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.133 +/- 0.04 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.152 +/- 0.026 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.149 +/- 0.055 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodDetected and Quantified2.318 +/- 2.231 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.094-0.764 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.012 +/- 0.01 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.007 - 0.03 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified86.0350 +/- 56.130 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified59.548 +/- 53.829 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified32.797 +/- 38.121 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified14.262 +/- 8.0185 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified122.250 +/- 132.109 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified3.746 (0.0329-20.401) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified0.81-2.0 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.63 +/- 0.04 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified3.115 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.300 +/- 2.450 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.61(0-38.1) umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified6.1 +/- 4.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.6 (0.4 - 0.9) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineDetected and Quantified1.0-2.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.255 +/- 4.639 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified17.6 +/- 6.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineDetected and Quantified7.732 +/- 3.666 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified7.7 (1.4-22.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified5.6 (1.4-15.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified0.67 +/- 2.94 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected and Quantified2.854 +/- 2.31 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified5.812 +/- 6.755 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified5.687 +/- 6.645 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
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 IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylacetic acid
METLIN ID5429
PubChem Compound12122
PDB IDNot Available
ChEBI ID17445
Food Biomarker OntologyNot Available
VMH ID3HPHAC
MarkerDB IDMDB00000161
Good Scents IDrw1190711
References
Synthesis ReferenceStaudenmaier, Horst Ralf; Hauer, Bernhard; Ladner, Wolfgang; Mueller, Ursula; Pressler, Uwe; Meyer, Joachim. Fermentative manufacture of 3-hydroxyphenylacetic acid. Ger. Offen. (1993), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [PubMed:6181210 ]
  2. Davis BA, Durden DA, Boulton AA: Plasma concentrations of p- and m-hydroxyphenylacetic acid and phenylacetic acid in humans: gas chromatographic--high-resolution mass spectrometric analysis. J Chromatogr. 1982 Jul 9;230(2):219-30. [PubMed:7107773 ]
  3. Davis BA, Boulton AA: Longitudinal urinary excretion of some "trace" acids in a human male. J Chromatogr. 1981 Feb 13;222(2):161-9. [PubMed:7251734 ]
  4. Nahmias C, Wahl LM, Amano S, Asselin MC, Chirakal R: Equilibration of 6-[18F]fluoro-L-m-tyrosine between plasma and erythrocytes. J Nucl Med. 2000 Oct;41(10):1636-41. [PubMed:11037992 ]
  5. Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
  6. Konishi Y: Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2005 Feb 9;53(3):601-7. [PubMed:15686408 ]
  7. Carey LC, Fabri PJ: Respiratory distress syndrome. Arch Surg. 1979 Mar;114(3):343. [PubMed:155437 ]
  8. Xiong X, Liu D, Wang Y, Zeng T, Peng Y: Urinary 3-(3-Hydroxyphenyl)-3-hydroxypropionic Acid, 3-Hydroxyphenylacetic Acid, and 3-Hydroxyhippuric Acid Are Elevated in Children with Autism Spectrum Disorders. Biomed Res Int. 2016;2016:9485412. doi: 10.1155/2016/9485412. Epub 2016 Mar 30. [PubMed:27123458 ]
  9. Martin M, Gibello A, Fernandez J, Ferrer E, Garrido-Pertierra A: Catabolism of 3- and 4-hydroxyphenylacetic acid by Klebsiella pneumoniae. J Gen Microbiol. 1991 Mar;137(3):621-8. doi: 10.1099/00221287-137-3-621. [PubMed:1851804 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Hydroxyphenylacetic acid → 6-[3-(carboxymethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-Hydroxyphenylacetic acid → 3,4,5-trihydroxy-6-{[2-(3-hydroxyphenyl)acetyl]oxy}oxane-2-carboxylic aciddetails
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-Hydroxyphenylacetic acid → 2-[3-(sulfooxy)phenyl]acetic aciddetails