MiMeDB: Showing metabocard for Phenylacetylglutamine (MMDBc0000775)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:40 UTC

Update Date

2024-04-30 19:33:39 UTC

Metabolite ID

MMDBc0000775

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 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>
MMDBc0000775

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₃H₁₆N₂O₄

Average Mass

264.2771

Monoisotopic Mass

264.11100701

IUPAC Name

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

Traditional Name

phenylacetylglutamine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-5d0fcec2811fdda6e493	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9210000000-b1470e0601bcb76fcdda	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0900000000-16da6849ac342b179bb0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0190000000-0e5d477fb2aa8bfecaba	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001l-0090000000-b74aefa0573c8e2d497c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9300000000-309b6dbe599b4262ff80	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-1790000000-34a22833325f47aff746	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-3900000000-2056d9abb5c0fdd85256	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-014r-0090000000-9a963271774da671d529	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-2950000000-506c649376dd55c452c1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-014i-0090000000-3cd0e6901a93d015f159	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001l-9200000000-25c13edfa9d657619b43	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1910000000-7f99e9784ad6de2851d8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-5900000000-a9229c68d62fec012834	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001l-9000000000-0f312f25ec486fde9a50	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0900000000-fc88effe954753003aa1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-3900000000-cd91c7242291d95e088e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0910000000-c889b0e15c63f54c93e1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-be097e5cfb29710afc22	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9500000000-09820d1b2dd8e5f5d551	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0910000000-bd099f1990927d0cc710	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-1590000000-43b5b1154ff8c459a8e4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-5950000000-d9a6090fc4170f3cbec0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-74c33c21f286a44eb712	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0290000000-c95723e9e5991b3a938f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02td-5980000000-c54142cded19fc0b1975	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-744617f4104fc833e5d6	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001927	L-Glutamine	Phenylacetylglutamine	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	12675874
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Mild cognitive impairment		Association	Human plasma	PubMed	27444566
Chronic kidney disease				PubMed	22626821
Uremic toxin				PubMed	22626821
Aging	increased	Association	Human urine	PubMed	23483888
Aging	increased	Association	Human urine	PubMed	23701591
Parkinson's disease	increased	Association	Human urine	PubMed	25271123
Chronic kidney disease	increased	Association	Human plasma	PubMed	26317986
Parkinson's disease	increased	Association	Human serum	PubMed	32357258
Uremic toxin				PubMed	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	2	Human stool; Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	6	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	3.34	0.31			uM	Adult (>18 years old)	Both	Normal	HMDB	8368503
Human Urine	Detected and Quantified	71	6			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	8368503
Human Blood	Detected and Quantified	201.894	169.318			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	<17.803				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Urine	Detected and Quantified	47.03		3.84	85.51	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19815468
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21784895
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Hemodialysis patients with colons	HMDB	21784895
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Hemodialysis patients without colons	HMDB	21784895
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected and Quantified	34		4.5	70	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	13.731	2.994			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	27.595	24.094			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	201.894	169.318			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	<17.803				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Blood	Detected and Quantified	3.34	0.31			uM	Adult (>18 years old)	Both	Normal	HMDB	8368503
Human Urine	Detected and Quantified	34.0		4.5	70.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	47.03		3.84	85.51	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19815468
Human Urine	Detected and Quantified	71.0	6.0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	8368503
Human Urine	Detected and Quantified	27.595	24.094			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	13.731	2.994			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21784895
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0006344

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1093/chromsci/21.12.546. [PubMed:6420430 ]
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. doi: 10.1021/ac9606463. [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 ]

Showing metabocard for Phenylacetylglutamine (MMDBc0000775)

MOL for #<Metabolite:0x00007fecfd094ee8>

3D MOL for #<Metabolite:0x00007fecfd094ee8>

3D SDF for #<Metabolite:0x00007fecfd094ee8>

3D-SDF for #<Metabolite:0x00007fecfd094ee8>

PDB for #<Metabolite:0x00007fecfd094ee8>

3D PDB for #<Metabolite:0x00007fecfd094ee8>

SMILES for #<Metabolite:0x00007fecfd094ee8>

INCHI for #<Metabolite:0x00007fecfd094ee8>

Structure for #<Metabolite:0x00007fecfd094ee8>

3D Structure for #<Metabolite:0x00007fecfd094ee8>