Showing metabocard for ortho-Hydroxyphenylacetic acid (MMDBc0047976)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-12-11 00:18:33 UTC
Update Date2024-10-15 21:59:31 UTC
Metabolite IDMMDBc0047976
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fab282714f8>

      
  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 #<Metabolite:0x00007fab282714f8>

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 #<Metabolite:0x00007fab282714f8>

      
  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>
MMDBc0047976

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fab282714f8>

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 #<Metabolite:0x00007fab282714f8>

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 #<Metabolite:0x00007fab282714f8>

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 #<Metabolite:0x00007fab282714f8>

OC(=O)CC1=C(O)C=CC=C1
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INCHI for #<Metabolite:0x00007fab282714f8>

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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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
Molecular FormulaC8H8O3
Average Mass152.1473
Monoisotopic Mass152.047344122
IUPAC Name2-(2-hydroxyphenyl)acetic acid
Traditional Nameo-hydroxyphenylacetic acid
CAS Registry NumberNot Available
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