Showing metabocard for p-Hydroxyphenylacetic acid (MMDBc0000491)

Plant
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:58 UTC
Update Date2022-08-31 06:07:09 UTC
Metabolite IDMMDBc0000491
Metabolite Identification
Common Namep-Hydroxyphenylacetic acid
Descriptionp-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929 , 12173102 ). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f124117e4e0>


  Mrv1652303182019222D          

 11 11  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -1.3275    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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f124117e4e0>

HMDB0000020
     RDKit          3D
p-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.4487    0.0429    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.1968    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -0.4203   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.0739   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892    0.4737   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.0988   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -0.6740   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.7166   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.3120    0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903   -0.1298    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4544    1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.0323   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    2.0547    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0052    1.2732   -1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.0591   -2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -1.1181   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.7342   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.1594    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791    0.8850    1.9925 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
  8 10  1  0
 10 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
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007f124117e4e0>


  Mrv1652303182019222D          

 11 11  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -1.3275    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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000491

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

> <INCHI_KEY>
XQXPVVBIMDBYFF-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.826780263933244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.508099347910598

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9984367127077793

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9585563884254755

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f124117e4e0>

HMDB0000020
     RDKit          3D
p-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.4487    0.0429    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.1968    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -0.4203   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.0739   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892    0.4737   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.0988   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -0.6740   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.7166   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.3120    0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903   -0.1298    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4544    1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.0323   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    2.0547    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0052    1.2732   -1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.0591   -2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -1.1181   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.7342   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.1594    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791    0.8850    1.9925 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
  8 10  1  0
 10 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
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007f124117e4e0>

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.960  -0.168   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.374  -2.478   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7   11   10                                                  
CONECT    9    4                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f124117e4e0>

COMPND    HMDB0000020
HETATM    1  O1  UNL     1      -2.449   0.043   1.827  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.623   0.197   0.593  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.663  -0.420  -0.072  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.646   1.074  -0.094  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.289   0.474  -0.078  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.225  -0.099  -1.228  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.475  -0.674  -1.158  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.243  -0.717  -0.017  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.510  -1.312   0.010  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.690  -0.130   1.120  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.439   0.454   1.073  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.453  -1.032  -0.883  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.645   2.055   0.394  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.005   1.273  -1.139  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.378  -0.059  -2.125  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.883  -1.118  -2.050  1.00  0.00           H  
HETATM   17  H6  UNL     1       4.317  -0.734  -0.197  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.289  -0.159   2.032  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.079   0.885   1.993  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   10
CONECT    9   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007f124117e4e0>

OC(=O)CC1=CC=C(O)C=C1
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INCHI for #<Metabolite:0x00007f124117e4e0>

InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
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Synonyms
ValueSource
(p-Hydroxyphenyl)acetic acidChEBI
4-CarboxymethylphenolChEBI
4-Hydroxybenzeneacetic acidChEBI
4-HydroxyphenylacetateChEBI
4-Hydroxyphenylacetic acidKegg
(p-Hydroxyphenyl)acetateGenerator
4-HydroxybenzeneacetateGenerator
p-HydroxyphenylacetateGenerator
(4-Hydroxy-phenyl)-acetateHMDB
(4-Hydroxy-phenyl)-acetic acidHMDB
(4-Hydroxy-phenyl)-essigsaeureHMDB
(4-Hydroxyphenyl)acetateHMDB
(4-Hydroxyphenyl)acetic acidHMDB
(p-Hydroxyphenyl)-acetateHMDB
(p-Hydroxyphenyl)-acetic acidHMDB
4-Hydroxy-benzeneacetateHMDB
4-Hydroxy-benzeneacetic acidHMDB
4-Hydroxyphenyl-acetic acidHMDB
Parahydroxy phenylacetateHMDB
Parahydroxy phenylacetic acidHMDB
ParahydroxyphenylacetateHMDB
Para-hydroxyphenylacetic acidHMDB
p-Hydroxyphenylacetic acidChEBI
4'-Hydroxyphenylacetic acidHMDB
2-(4-Hydroxyphenyl)acetic acidHMDB
Molecular FormulaC8H8O3
Average Mass152.1473
Monoisotopic Mass152.047344122
IUPAC Name2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxyphenylacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyXQXPVVBIMDBYFF-UHFFFAOYSA-N