Showing metabocard for N-Phenylacetylglycine (MMDBc0033545)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:52:59 UTC
Update Date2024-04-30 20:12:23 UTC
Metabolite IDMMDBc0033545
Metabolite Identification
Common NameN-Phenylacetylglycine
DescriptionPhenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292 ) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound (PMID: 7492634 ) while NMR studies claimed to have identified it (PMID: 21167146 ). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f91fa294828>

Phenylacetylglycine.mol
  Mrv1652305271900262D          

 14 14  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
    1.4289    0.0000    0.0000 C   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
  8  9  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f91fa294828>

HMDB0000821
     RDKit          3D
Phenylacetylglycine
 25 25  0  0  0  0  0  0  0  0999 V2000
   -4.5919    0.0258    0.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4473    0.1087   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568    0.2019   -1.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    0.1066   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1257   -0.0007    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -0.0217   -0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.0512   -1.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -0.1297    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503   -0.1316    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.0679    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934    1.0816   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2396   -0.0761   -0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -1.2758   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141   -1.2783   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0861    1.0519   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410    1.0225   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -0.8149   -1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.0639    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256   -1.1242    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736    0.6243    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    1.9708    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898    2.0436   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2288   -0.0099   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -2.2143   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706   -2.2159   -0.0192 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  8 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f91fa294828>

Phenylacetylglycine.mol
  Mrv1652305271900262D          

 14 14  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
    1.4289    0.0000    0.0000 C   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
  8  9  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033545

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

> <INCHI_KEY>
UTYVDVLMYQPLQB-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.085212338243267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-phenylacetamido)acetic acid

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.5057108656666667

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.646653717913555

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.985264151206934

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9261944657280297

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
50.169100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f91fa294828>

HMDB0000821
     RDKit          3D
Phenylacetylglycine
 25 25  0  0  0  0  0  0  0  0999 V2000
   -4.5919    0.0258    0.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4473    0.1087   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568    0.2019   -1.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    0.1066   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1257   -0.0007    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -0.0217   -0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.0512   -1.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -0.1297    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503   -0.1316    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.0679    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934    1.0816   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2396   -0.0761   -0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -1.2758   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141   -1.2783   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0861    1.0519   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410    1.0225   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -0.8149   -1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.0639    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256   -1.1242    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736    0.6243    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    1.9708    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898    2.0436   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2288   -0.0099   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -2.2143   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706   -2.2159   -0.0192 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  8 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
M  END
Download

PDB for #<Metabolite:0x00007f91fa294828>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Phenylacetylglycine.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    8    2                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9   10   14    8                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for #<Metabolite:0x00007f91fa294828>

COMPND    HMDB0000821
HETATM    1  O1  UNL     1      -4.592   0.026   0.818  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.447   0.109  -0.413  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.557   0.202  -1.220  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.097   0.107  -0.993  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.126  -0.001   0.077  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.737  -0.022  -0.256  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.356   0.051  -1.452  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.303  -0.130   0.791  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.650  -0.132   0.210  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.330   1.068   0.019  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.593   1.082  -0.524  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.240  -0.076  -0.902  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.581  -1.276  -0.720  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.314  -1.278  -0.174  1.00  0.00           C  
HETATM   15  H1  UNL     1      -6.086   1.052  -1.383  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.941   1.023  -1.605  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.926  -0.815  -1.629  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.392  -0.064   1.084  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.126  -1.124   1.297  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.174   0.624   1.594  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.808   1.971   0.321  1.00  0.00           H  
HETATM   22  H8  UNL     1       4.090   2.044  -0.657  1.00  0.00           H  
HETATM   23  H9  UNL     1       5.229  -0.010  -1.323  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.050  -2.214  -1.002  1.00  0.00           H  
HETATM   25  H11 UNL     1       1.771  -2.216  -0.019  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6   18
CONECT    6    7    7    8
CONECT    8    9   19   20
CONECT    9   10   10   14
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13   23
CONECT   13   14   14   24
CONECT   14   25
END
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SMILES for #<Metabolite:0x00007f91fa294828>

OC(=O)CNC(=O)CC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f91fa294828>

InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)
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Synonyms
ValueSource
N-PhenacetylglycineChEBI
N-PhenylacetylglycineChEBI
Phenaceturic acidChEBI
PhenacetylglycineChEBI
PhenacetateGenerator
Phenacetic acidGenerator
((Phenylacetyl)amino)acetic acidHMDB
N-(Phenylacetyl)-glycineHMDB
N-(Phenylacetyl)glycineHMDB
PAAHMDB
PAGHMDB
PhenaceturateHMDB
Phenylacetyl glycineHMDB
[(Phenylacetyl)amino]acetateHMDB
[(Phenylacetyl)amino]acetic acidHMDB
PhenylacetylglycineMeSH
Molecular FormulaC10H11NO3
Average Mass193.1992
Monoisotopic Mass193.073893223
IUPAC Name2-(2-phenylacetamido)acetic acid
Traditional Namephenylacetylglycine
CAS Registry Number500-98-1
SMILES
OC(=O)CNC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)
InChI KeyUTYVDVLMYQPLQB-UHFFFAOYSA-N