Showing metabocard for Phenylacetic acid (MMDBc0000068)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:13 UTC
Update Date2024-04-30 19:30:58 UTC
Metabolite IDMMDBc0000068
Metabolite Identification
Common NamePhenylacetic acid
DescriptionPhenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU), an inborn error of metabolism. Phenyl acetate has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765 , 476920 , 6857245 ). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters' and in many fruits. As a result it is used as a perfumery and flavoring ingredient. Phenyl acetate is a microbial metabolite.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2a87020a0>


  Mrv1652309272007372D          

 10 10  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  2  0  0  0  0
  3 10  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  2  2  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fe2a87020a0>

HMDB0000209
     RDKit          3D
Phenylacetic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    1.8439   -1.1936   -1.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038   -0.5513   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -0.5743   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770    0.2113    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.1586    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8004   -0.8066    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.7575    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.2030   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    1.1649   -1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4748    1.1207   -0.6767 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0763   -0.9324    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532    1.2851    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -0.2288    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.5476    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -1.5295    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919    0.1664   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    1.9100   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.9017   -1.1110 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  5  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007fe2a87020a0>


  Mrv1652309272007372D          

 10 10  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  2  0  0  0  0
  3 10  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  2  2  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000068

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

> <INCHI_KEY>
WLJVXDMOQOGPHL-UHFFFAOYSA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.1479

> <EXACT_MASS>
136.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.849901131444868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylacetic acid

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.610994105333333

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.546943579612796

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
37.3656

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ω-phenylacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fe2a87020a0>

HMDB0000209
     RDKit          3D
Phenylacetic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    1.8439   -1.1936   -1.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038   -0.5513   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -0.5743   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770    0.2113    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.1586    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8004   -0.8066    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.7575    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.2030   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    1.1649   -1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4748    1.1207   -0.6767 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0763   -0.9324    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532    1.2851    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -0.2288    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.5476    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -1.5295    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919    0.1664   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    1.9100   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.9017   -1.1110 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  5  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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PDB for #<Metabolite:0x00007fe2a87020a0>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1   10    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    8    9   10                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x00007fe2a87020a0>

COMPND    HMDB0000209
HETATM    1  O1  UNL     1       1.844  -1.194  -1.417  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.304  -0.551  -0.446  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.677  -0.574  -0.253  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.477   0.211   0.482  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.033   0.159   0.172  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.800  -0.807   0.697  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.130  -0.758   0.337  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.630   0.203  -0.509  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.807   1.165  -1.034  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.475   1.121  -0.677  1.00  0.00           C  
HETATM   11  H1  UNL     1       4.076  -0.932   0.620  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.753   1.285   0.537  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.583  -0.229   1.515  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.384  -1.548   1.357  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.769  -1.529   0.764  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.692   0.166  -0.739  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.222   1.910  -1.697  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.161   1.902  -1.111  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5   12   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   18
END
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SMILES for #<Metabolite:0x00007fe2a87020a0>

OC(=O)CC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007fe2a87020a0>

InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
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Synonyms
ValueSource
2-PHENYLACETIC ACIDChEBI
2-Phenylethanoic acidChEBI
alpha-Toluic acidChEBI
Benzeneacetic acidChEBI
Benzylformic acidChEBI
Omega-phenylacetic acidChEBI
PAChEBI
PhenylacetateKegg
2-PHENYLACETateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
Α-toluateGenerator
Α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylethanoateHMDB
W-PhenylacetateHMDB
W-Phenylacetic acidHMDB
Phenylacetic acid, potassium saltHMDB
Sodium phenylacetateHMDB
Phenylacetic acid, lithium saltHMDB
Phenylacetic acid, sodium saltHMDB
Phenylacetic acid, ammonium saltHMDB
Phenylacetic acid, calcium saltHMDB
Phenylacetic acid, cesium saltHMDB
Phenylacetic acid, mercury saltHMDB
Phenylacetic acid, rubidium saltHMDB
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPDHMDB
PAAPhytoBank
ω-Phenylacetic acidPhytoBank
Phenylacetic acidHMDB
Molecular FormulaC8H8O2
Average Mass136.1479
Monoisotopic Mass136.0524295
IUPAC Name2-phenylacetic acid
Traditional Nameω-phenylacetic acid
CAS Registry Number103-82-2
SMILES
OC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N