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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 01:14:41 UTC

Update Date

2024-05-19 04:24:16 UTC

HMDB ID

HMDB0006344

Secondary Accession Numbers

HMDB06344

Metabolite Identification

Common Name

Phenylacetylglutamine

Description

Phenylacetylglutamine is a product formed from the conjugation of phenylacetate and glutamine. Technically, it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals such as the dog, cat, rat, monkey, sheep, and horse do not excrete this compound. Phenylacetyl-CoA and L-glutamine react to form phenylacetylglutamine and coenzyme A. The enzyme (glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a polypeptide species distinct from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia (PMID: 2791363 , 8972626 ). It has been shown that over 50% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidney's preferential filtration of conjugated phenylacetic acid (PMID: 6420430 ). Phenylacetylglutamine is elevated by a factor of two or more in the urine of patients with diet-controlled PKU or phenylketonuria (PMID: 34441968 ). Phenylacetylglutamine is a microbial metabolite found in Christensenellaceae, Lachnospiraceae and Ruminococcaceae (PMID: 26241311 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0006344
     RDKit          3D
Phenylacetylglutamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.4692    0.5084   -1.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069   -0.4106   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -1.4237   -2.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.2047   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.3276   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -1.1543    0.6167 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5785    0.0796    0.4105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.0549    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.0508    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    1.3105   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    1.0347   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398    0.8446   -1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786    0.5854   -1.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.5213   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174    0.7055    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858    0.9611    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -1.2254    1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -0.2966    2.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -2.3410    2.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2943    1.5304   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4423    0.1593   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -0.0635    0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.7518   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.3475   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.3028   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -2.0140    0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.9867    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623    1.9971    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.8848   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383    0.9002   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385    0.4382   -2.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.3194   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650    0.6635    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125    1.1118    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -2.1869    2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  7 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
M  END

      
  Mrv1652305301819242D          

 19 19  0  0  0  0            999 V2000
10001.922210001.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.207410001.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.493310001.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.779310001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.493310000.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.634810001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.349810001.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.062610001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.777510001.1927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.062610002.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.922210000.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6348 9999.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2074 9999.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.065510001.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.350910001.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.636310001.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.636310000.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3509 9999.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.065610000.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006344

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1

> <INCHI_KEY>
JFLIEFSWGNOPJJ-JTQLQIEISA-N

> <FORMULA>
C13H16N2O4

> <MOLECULAR_WEIGHT>
264.2771

> <EXACT_MASS>
264.11100701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.55439529399692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-0.08561821066666678

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.01470691027999

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8975375279453566

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5334406653959398

> <JCHEM_POLAR_SURFACE_AREA>
109.49

> <JCHEM_REFRACTIVITY>
67.27560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetylglutamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006344
     RDKit          3D
Phenylacetylglutamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.4692    0.5084   -1.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069   -0.4106   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -1.4237   -2.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.2047   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.3276   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -1.1543    0.6167 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5785    0.0796    0.4105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.0549    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.0508    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    1.3105   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    1.0347   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398    0.8446   -1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786    0.5854   -1.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.5213   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174    0.7055    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858    0.9611    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -1.2254    1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -0.2966    2.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -2.3410    2.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2943    1.5304   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4423    0.1593   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -0.0635    0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.7518   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.3475   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.3028   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -2.0140    0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.9867    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623    1.9971    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.8848   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383    0.9002   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385    0.4382   -2.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.3194   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650    0.6635    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125    1.1118    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -2.1869    2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  7 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 30-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-18         0                                  
HETATM    1  C   UNK     0    8670.2558668.893   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8668.9208669.662   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8667.5878668.893   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.2558669.662   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.5878667.355   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8671.5858669.662   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.9208668.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.2508669.662   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8675.5858668.893   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    8674.2508671.200   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8670.2558667.355   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8671.5858666.584   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8668.9208666.584   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.9228668.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.5888669.664   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.2548668.894   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.2548667.354   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.5888666.584   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.9228667.354   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3   14                                                       
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   15   19    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0006344
HETATM    1  N1  UNL     1       5.469   0.508  -1.667  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.407  -0.411  -1.472  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.383  -1.424  -2.244  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.375  -0.205  -0.422  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.361  -1.328  -0.427  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.307  -1.154   0.617  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.579   0.080   0.410  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.817   0.055   0.132  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.429  -1.051   0.063  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.546   1.311  -0.076  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.974   1.035  -0.349  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.440   0.845  -1.636  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.779   0.585  -1.897  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.649   0.521  -0.818  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.217   0.706   0.470  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.886   0.961   0.704  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.848  -1.225   1.998  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.657  -0.297   2.825  1.00  0.00           O  
HETATM   19  O4  UNL     1       2.578  -2.341   2.382  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.294   1.530  -1.670  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.442   0.159  -1.811  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.822  -0.064   0.581  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.842   0.752  -0.658  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.860  -1.347  -1.414  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.860  -2.303  -0.304  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.601  -2.014   0.517  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.089   0.987   0.469  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.462   1.997   0.805  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.164   1.885  -0.965  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.738   0.900  -2.457  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.138   0.438  -2.895  1.00  0.00           H  
HETATM   32  H13 UNL     1      -6.713   0.319  -0.978  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.865   0.664   1.341  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.512   1.112   1.716  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.555  -2.187   2.607  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    4
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   17   26
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   28   29
CONECT   11   12   12   16
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   34
CONECT   17   18   18   19
CONECT   19   35
END

HMDB0006344
     RDKit          3D
Phenylacetylglutamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.4692    0.5084   -1.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069   -0.4106   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -1.4237   -2.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.2047   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.3276   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -1.1543    0.6167 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5785    0.0796    0.4105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.0549    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.0508    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    1.3105   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    1.0347   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398    0.8446   -1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786    0.5854   -1.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.5213   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174    0.7055    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858    0.9611    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -1.2254    1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -0.2966    2.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -2.3410    2.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2943    1.5304   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4423    0.1593   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -0.0635    0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.7518   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.3475   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.3028   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -2.0140    0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.9867    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623    1.9971    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.8848   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383    0.9002   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385    0.4382   -2.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.3194   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650    0.6635    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125    1.1118    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -2.1869    2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  7 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-N-Phenylacetyl-L-glutamine	ChEBI
Phenylacetyl-L-glutamine	ChEBI
N2-(2-Phenylacetyl)-L-glutamine	Kegg
a-N-Phenylacetyl-L-glutamine	Generator
Α-N-phenylacetyl-L-glutamine	Generator
Phenylacetylglutamine	ChEBI
N(2)-(Phenylacetyl)-L-glutamine	HMDB
N(2)-(2-Phenylacetyl)-L-glutamine	Generator, HMDB
N-Phenylacetylglutamine	HMDB
N2-(Phenylacetyl)-L-glutamine	HMDB
α-N-Phenylacetylglutamine	HMDB
alpha-N-Phenylacetylglutamine	Generator, HMDB

Chemical Formula

C₁₃H₁₆N₂O₄

Average Molecular Weight

264.2771

Monoisotopic Molecular Weight

264.11100701

IUPAC Name

(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid

Traditional Name

phenylacetylglutamine

CAS Registry Number

28047-15-6

SMILES

NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1

InChI Key

JFLIEFSWGNOPJJ-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N(2)-phenylacetylglutamine (CHEBI:17884 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Renal system and urinary system

Renal disorder

Uremia (HMDB: HMDB0006344)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8368503)

Organ

Placenta (HMDB: HMDB0006344)

Excreta

Biofluid or Excreta

Urine (PMID: 8368503)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0006344)
Extracellular (HMDB: HMDB0006344)

Source

Endogenous

Endogenous (HMDB: HMDB0006344)

Microbe

Exogenous

Exogenous (HMDB: HMDB0006344)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Meats (HMDB: HMDB0006344)
Legumes (HMDB: HMDB0006344)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0006344)

Nut

Nuts (HMDB: HMDB0006344)

Milk and milk product

Dairy products (HMDB: HMDB0006344)

Egg

Eggs (HMDB: HMDB0006344)

Soy

Soy (HMDB: HMDB0006344)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phenylacetate Metabolism (HMDB: HMDB0006344)
Phenylacetate Metabolism (PathBank: SMP0087208)

Role

Biological role

Waste product (PMID: 35448883)

Industrial application

Pharmaceutical industry

Biomarker

Uremia (MarkerDB: MDB00000483)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	166.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000067
[M+H]+	Not Available	159.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000067

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	-0.35	ALOGPS
logP	-0.086	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.28 m³·mol⁻¹	ChemAxon
Polarizability	26.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.379	31661259
DarkChem	[M-H]-	160.136	31661259
DeepCCS	[M+H]+	159.421	30932474
DeepCCS	[M-H]-	157.063	30932474
DeepCCS	[M-2H]-	189.949	30932474
DeepCCS	[M+Na]+	165.514	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	160.8	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	3.48 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9998 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	176.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1191.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	229.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	326.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	618.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	739.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	311.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	932.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	144.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylacetylglutamine	NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O	3623.9	Standard polar	33892256
Phenylacetylglutamine	NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O	2342.7	Standard non polar	33892256
Phenylacetylglutamine	NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O	2631.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylacetylglutamine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(N)=O)NC(=O)CC1=CC=CC=C1	2440.1	Semi standard non polar	33892256
Phenylacetylglutamine,1TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O	2493.7	Semi standard non polar	33892256
Phenylacetylglutamine,1TMS,isomer #3	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(N)=O)C(=O)O	2433.2	Semi standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2492.5	Semi standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2421.2	Standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	3115.4	Standard polar	33892256
Phenylacetylglutamine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2400.3	Semi standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2339.5	Standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	3491.6	Standard polar	33892256
Phenylacetylglutamine,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2576.1	Semi standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2494.1	Standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3323.4	Standard polar	33892256
Phenylacetylglutamine,2TMS,isomer #4	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2445.2	Semi standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #4	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2472.1	Standard non polar	33892256
Phenylacetylglutamine,2TMS,isomer #4	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	3229.1	Standard polar	33892256
Phenylacetylglutamine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)NC(=O)CC1=CC=CC=C1	2533.2	Semi standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)NC(=O)CC1=CC=CC=C1	2507.9	Standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)NC(=O)CC1=CC=CC=C1	2939.7	Standard polar	33892256
Phenylacetylglutamine,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2433.2	Semi standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2469.8	Standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2915.7	Standard polar	33892256
Phenylacetylglutamine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2502.9	Semi standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2570.8	Standard non polar	33892256
Phenylacetylglutamine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3062.2	Standard polar	33892256
Phenylacetylglutamine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2503.0	Semi standard non polar	33892256
Phenylacetylglutamine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2563.3	Standard non polar	33892256
Phenylacetylglutamine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2793.8	Standard polar	33892256
Phenylacetylglutamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(N)=O)NC(=O)CC1=CC=CC=C1	2693.1	Semi standard non polar	33892256
Phenylacetylglutamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O	2732.4	Semi standard non polar	33892256
Phenylacetylglutamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(N)=O)C(=O)O	2674.4	Semi standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2941.2	Semi standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2783.9	Standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3251.6	Standard polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2891.0	Semi standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2759.6	Standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(N)=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3537.1	Standard polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3037.9	Semi standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2850.1	Standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3351.3	Standard polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2924.7	Semi standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2817.9	Standard non polar	33892256
Phenylacetylglutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3315.1	Standard polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(=O)CC1=CC=CC=C1	3223.5	Semi standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(=O)CC1=CC=CC=C1	3046.6	Standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(=O)CC1=CC=CC=C1	3172.7	Standard polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3100.3	Semi standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2996.9	Standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3192.3	Standard polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3205.5	Semi standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3078.9	Standard non polar	33892256
Phenylacetylglutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3252.1	Standard polar	33892256
Phenylacetylglutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3361.4	Semi standard non polar	33892256
Phenylacetylglutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3252.6	Standard non polar	33892256
Phenylacetylglutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3122.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglutamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-5d0fcec2811fdda6e493	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglutamine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9210000000-b1470e0601bcb76fcdda	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglutamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine Linear Ion Trap , negative-QTOF	splash10-0002-0900000000-16da6849ac342b179bb0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine Linear Ion Trap , positive-QTOF	splash10-00di-0190000000-0e5d477fb2aa8bfecaba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine Linear Ion Trap , positive-QTOF	splash10-001l-0090000000-b74aefa0573c8e2d497c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 30V, Positive-QTOF	splash10-001i-9300000000-309b6dbe599b4262ff80	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Positive-QTOF	splash10-0019-1790000000-34a22833325f47aff746	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 35V, Positive-QTOF	splash10-001i-3900000000-2056d9abb5c0fdd85256	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 0V, Positive-QTOF	splash10-014r-0090000000-9a963271774da671d529	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Positive-QTOF	splash10-001r-2950000000-506c649376dd55c452c1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 0V, Positive-QTOF	splash10-014i-0090000000-3cd0e6901a93d015f159	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 30V, Positive-QTOF	splash10-001l-9200000000-25c13edfa9d657619b43	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Positive-QTOF	splash10-001i-1910000000-7f99e9784ad6de2851d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 20V, Positive-QTOF	splash10-001i-5900000000-a9229c68d62fec012834	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 40V, Positive-QTOF	splash10-001l-9000000000-0f312f25ec486fde9a50	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 20V, Negative-QTOF	splash10-002b-0900000000-fc88effe954753003aa1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 30V, Negative-QTOF	splash10-004i-3900000000-cd91c7242291d95e088e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Negative-QTOF	splash10-0002-0910000000-c889b0e15c63f54c93e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 35V, Negative-QTOF	splash10-0002-0900000000-be097e5cfb29710afc22	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 40V, Negative-QTOF	splash10-054o-9500000000-09820d1b2dd8e5f5d551	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Negative-QTOF	splash10-0002-0910000000-bd099f1990927d0cc710	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Positive-QTOF	splash10-00kb-1590000000-43b5b1154ff8c459a8e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 20V, Positive-QTOF	splash10-0002-5950000000-d9a6090fc4170f3cbec0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 40V, Positive-QTOF	splash10-0006-9300000000-74c33c21f286a44eb712	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 10V, Negative-QTOF	splash10-03di-0290000000-c95723e9e5991b3a938f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 20V, Negative-QTOF	splash10-02td-5980000000-c54142cded19fc0b1975	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglutamine 40V, Negative-QTOF	splash10-0006-9200000000-744617f4104fc833e5d6	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Phenylalanine metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.34 +/- 0.31 uM	Adult (>18 years old)	Both	Normal	8368503	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21784895	details
Blood	Detected and Quantified	<17.803 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	71.0 +/- 6.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8368503	details
Urine	Detected and Quantified	47.03 (3.84 - 85.51) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19815468	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected and Quantified	34.0 (4.5-70.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	13.731 +/- 2.994 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	22.67 (17.32-33.98) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hemodialysis patients with colons	21784895	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hemodialysis patients without colons	21784895	details
Blood	Detected and Quantified	201.894 +/- 169.318 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected and Quantified	27.595 +/- 24.094 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Uremia
Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Colorectal cancer
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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Phenylacetylglutamine

METLIN ID

Not Available

PubChem Compound

92258

PDB ID

Not Available

ChEBI ID

17884

Food Biomarker Ontology

Not Available

VMH ID

PHEACGLN

MarkerDB ID

MDB00000483

Good Scents ID

Not Available

References

Synthesis Reference

Suyama, Tadashi; Toyoda, Takeshi; Kanao, Seizo. N-Phenylacetyl amino acids and their homologs. I. N-Acylamino acids. Yakugaku Zasshi (1965), 85(4), 279-83. CODEN: YKKZAJ ISSN:0031-6903. CAN 63:39385 AN 1965:439385

Material Safety Data Sheet (MSDS)

Not Available

General References

Karoum F, Chuang LW, Mosnaim AD, Staub RA, Wyatt RJ: Plasma and cerebrospinal fluid concentration of phenylacetic acid in humans and monkeys. J Chromatogr Sci. 1983 Dec;21(12):546-50. [PubMed:6420430 ]
Zimmerman L, Egestad B, Jornvall H, Bergstrom J: Identification and determination of phenylacetylglutamine, a major nitrogenous metabolite in plasma of uremic patients. Clin Nephrol. 1989 Sep;32(3):124-8. [PubMed:2791363 ]
Shockcor JP, Unger SE, Wilson ID, Foxall PJ, Nicholson JK, Lindon JC: Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine. Anal Chem. 1996 Dec 15;68(24):4431-5. [PubMed:8972626 ]
Barrios C, Beaumont M, Pallister T, Villar J, Goodrich JK, Clark A, Pascual J, Ley RE, Spector TD, Bell JT, Menni C: Gut-Microbiota-Metabolite Axis in Early Renal Function Decline. PLoS One. 2015 Aug 4;10(8):e0134311. doi: 10.1371/journal.pone.0134311. eCollection 2015. [PubMed:26241311 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Andrade F, Cano A, Unceta Suarez M, Arza A, Vinuesa A, Ceberio L, Lopez-Osle N, de Frutos G, Lopez-Oceja R, Aznal E, Gonzalez-Lamuno D, de Las Heras J: Urine Phenylacetylglutamine Determination in Patients with Hyperphenylalaninemia. J Clin Med. 2021 Aug 19;10(16):3674. doi: 10.3390/jcm10163674. [PubMed:34441968 ]

Showing metabocard for Phenylacetylglutamine (HMDB0006344)

MOL for HMDB0006344 (Phenylacetylglutamine)

3D MOL for HMDB0006344 (Phenylacetylglutamine)

3D SDF for HMDB0006344 (Phenylacetylglutamine)

3D-SDF for HMDB0006344 (Phenylacetylglutamine)

PDB for HMDB0006344 (Phenylacetylglutamine)

3D PDB for HMDB0006344 (Phenylacetylglutamine)

SMILES for HMDB0006344 (Phenylacetylglutamine)

INCHI for HMDB0006344 (Phenylacetylglutamine)

Structure for HMDB0006344 (Phenylacetylglutamine)

3D Structure for HMDB0006344 (Phenylacetylglutamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra