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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:04:03 UTC

Update Date

2022-03-07 03:17:36 UTC

HMDB ID

HMDB0059782

Secondary Accession Numbers

HMDB59782

Metabolite Identification

Common Name

N-Phenylacetyl pyroglutamic acid

Description

N-Phenylacetyl pyroglutamic acid belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. N-Phenylacetyl pyroglutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Structure

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

HMDB0059782
     RDKit          3D
N-Phenylacetyl pyroglutamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.7148   -1.4727   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.9525    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -1.7073    0.9404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    0.4341   -0.0295 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1306    1.4216    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486    1.7861    1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.4018    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675    1.6478    3.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.7435    0.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    0.4587    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    0.7839    1.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -0.2355   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381   -0.4113   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621   -1.5196   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3243   -1.7035   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -0.7114   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.4127   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1694    0.5682   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9910   -0.7683   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048   -1.6794    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276   -2.4259   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869    0.6115   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277    0.9439    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    2.2847   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    2.8680    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532    1.1960    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.3507   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.2319   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.2948    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -2.6092    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1692   -0.8126   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1726    1.1667   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.4563   -1.6452 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

2,3,4,5-tetrahydroxypentanoic acid
  Mrv0541 02261312042D          

 18 19  0  0  0  0            999 V2000
    3.5946    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4512    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368    1.2964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4512    0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    2.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5689    1.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    0.9609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2636    2.6689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1884    0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246   -0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -0.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  2  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
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  2  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059782

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H15NO3/c1-10(16)12-7-8-13(17)15(12)14(18)9-11-5-3-2-4-6-11/h2-6,12H,7-9H2,1H3/t12-/m0/s1

> <INCHI_KEY>
ASNIYCYEXPHRFD-LBPRGKRZSA-N

> <FORMULA>
C14H15NO3

> <MOLECULAR_WEIGHT>
245.2738

> <EXACT_MASS>
245.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.33378424975476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-acetyl-1-(2-phenylacetyl)pyrrolidin-2-one

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.2629039456666664

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.797623384757877

> <JCHEM_PKA_STRONGEST_BASIC>
-6.707746132850191

> <JCHEM_POLAR_SURFACE_AREA>
54.45

> <JCHEM_REFRACTIVITY>
65.92670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-acetyl-1-(2-phenylacetyl)pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059782
     RDKit          3D
N-Phenylacetyl pyroglutamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.7148   -1.4727   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.9525    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -1.7073    0.9404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    0.4341   -0.0295 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1306    1.4216    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486    1.7861    1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.4018    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675    1.6478    3.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.7435    0.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    0.4587    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    0.7839    1.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -0.2355   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381   -0.4113   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621   -1.5196   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3243   -1.7035   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -0.7114   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.4127   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1694    0.5682   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9910   -0.7683   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048   -1.6794    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276   -2.4259   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869    0.6115   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277    0.9439    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    2.2847   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    2.8680    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532    1.1960    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.3507   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.2319   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.2948    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -2.6092    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1692   -0.8126   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1726    1.1667   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.4563   -1.6452 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2,3,4,5-tetrahydroxypentanoic acid                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         0                                  
HETATM    1  C   UNK     0       6.710   2.420   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.376   1.650   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.376   0.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.710  -0.660   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.044   0.110   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.044   1.650   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.043   2.420   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.709   1.650   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.375   2.420   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.709   0.110   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.214   3.952   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.292   4.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.062   2.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.032   1.794   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.359   4.982   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.352   0.287   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.793  -0.743   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.816  -0.189   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11   14                                                  
CONECT   10    8                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13   16                                                  
CONECT   15   11                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0059782
HETATM    1  C1  UNL     1       3.715  -1.473  -0.628  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.562  -0.953   0.152  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.023  -1.707   0.940  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.091   0.434  -0.030  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.131   1.422   0.398  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.849   1.786   1.821  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.428   1.402   1.991  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.768   1.648   3.049  1.00  0.00           O  
HETATM    9  N1  UNL     1       0.957   0.743   0.823  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.411   0.459   0.580  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.296   0.784   1.407  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.865  -0.236  -0.661  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.338  -0.411  -0.671  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.962  -1.520  -0.149  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.324  -1.703  -0.146  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.106  -0.711  -0.704  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.534   0.413  -1.237  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.169   0.568  -1.225  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.991  -0.768  -1.453  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.605  -1.679   0.025  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.428  -2.426  -1.146  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.787   0.611  -1.102  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.128   0.944   0.344  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.125   2.285  -0.299  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.006   2.868   2.013  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.453   1.196   2.539  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.563   0.351  -1.552  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.360  -1.232  -0.727  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.345  -2.295   0.287  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.725  -2.609   0.287  1.00  0.00           H  
HETATM   31  H13 UNL     1      -6.169  -0.813  -0.723  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.173   1.167  -1.664  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.702   1.456  -1.645  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5    9   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   27   28
CONECT   13   14   14   18
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   33
END

HMDB0059782
     RDKit          3D
N-Phenylacetyl pyroglutamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.7148   -1.4727   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.9525    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -1.7073    0.9404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    0.4341   -0.0295 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1306    1.4216    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486    1.7861    1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.4018    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675    1.6478    3.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.7435    0.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    0.4587    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    0.7839    1.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -0.2355   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381   -0.4113   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621   -1.5196   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3243   -1.7035   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -0.7114   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.4127   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1694    0.5682   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9910   -0.7683   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048   -1.6794    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276   -2.4259   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869    0.6115   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277    0.9439    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    2.2847   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    2.8680    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532    1.1960    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.3507   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.2319   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.2948    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -2.6092    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1692   -0.8126   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1726    1.1667   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.4563   -1.6452 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Phenylacetyl pyroglutamate	Generator

Chemical Formula

C₁₄H₁₅NO₃

Average Molecular Weight

245.2738

Monoisotopic Molecular Weight

245.105193351

IUPAC Name

(5S)-5-acetyl-1-(2-phenylacetyl)pyrrolidin-2-one

Traditional Name

(5S)-5-acetyl-1-(2-phenylacetyl)pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H15NO3/c1-10(16)12-7-8-13(17)15(12)14(18)9-11-5-3-2-4-6-11/h2-6,12H,7-9H2,1H3/t12-/m0/s1

InChI Key

ASNIYCYEXPHRFD-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
N-acylpyrrolidine
Carboxylic acid imide, n-substituted
Pyrrolidone
2-pyrrolidone
Carboxylic acid imide
Dicarboximide
Pyrrolidine
Ketone
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 2338430)

Source

Exogenous

Exogenous (HMDB: HMDB0059782)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.26	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	18.8	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	54.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.93 m³·mol⁻¹	ChemAxon
Polarizability	25.33 Å³	ChemAxon
Number of Rings	2	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]+	157.304	31661259
DarkChem	[M-H]-	154.571	31661259
DeepCCS	[M+H]+	153.988	30932474
DeepCCS	[M-H]-	151.593	30932474
DeepCCS	[M-2H]-	184.692	30932474
DeepCCS	[M+Na]+	159.901	30932474
AllCCS	[M+H]+	157.0	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	160.5	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	159.0	32859911
AllCCS	[M+Na-2H]-	159.0	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylacetyl pyroglutamic acid	CC(=O)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	3113.9	Standard polar	33892256
N-Phenylacetyl pyroglutamic acid	CC(=O)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2178.7	Standard non polar	33892256
N-Phenylacetyl pyroglutamic acid	CC(=O)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2037.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2276.0	Semi standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2107.7	Standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2743.8	Standard polar	33892256
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2133.1	Semi standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2045.7	Standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2790.9	Standard polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2471.9	Semi standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2300.3	Standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC(=O)N1C(=O)CC1=CC=CC=C1	2887.4	Standard polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2344.6	Semi standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2266.5	Standard non polar	33892256
N-Phenylacetyl pyroglutamic acid,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCC(=O)N1C(=O)CC1=CC=CC=C1	2904.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetyl pyroglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-8290000000-bb211faa5e270aaf953b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetyl pyroglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetyl pyroglutamic acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 10V, Positive-QTOF	splash10-002b-0390000000-9a697b5b40e4a29be681	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 20V, Positive-QTOF	splash10-002f-9670000000-c93b7beb6fe7f6995249	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 40V, Positive-QTOF	splash10-0006-9400000000-910f4f9a706bcbb91f01	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 10V, Negative-QTOF	splash10-0006-0190000000-e9de42f335546b811f1e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 20V, Negative-QTOF	splash10-004l-1980000000-68a40a66edd271bc7503	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 40V, Negative-QTOF	splash10-00o4-9500000000-64b8e79ce0b86bf8ac87	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 10V, Negative-QTOF	splash10-0059-6940000000-2feda9a3591147bce9b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 20V, Negative-QTOF	splash10-005c-7920000000-c12e186e5ba5bc882776	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 40V, Negative-QTOF	splash10-0006-9200000000-32eb1bf043edaf56c384	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 10V, Positive-QTOF	splash10-0002-2390000000-91e87291ca317f17929f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 20V, Positive-QTOF	splash10-0006-9110000000-1ad97b1650efac076f5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetyl pyroglutamic acid 40V, Positive-QTOF	splash10-0006-9200000000-6da5057c9c1d0d8ce0e4	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	2338430	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124202114

PDB ID

Not Available

ChEBI ID

89848

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Phenylacetyl pyroglutamic acid (HMDB0059782)

MOL for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

3D MOL for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

3D SDF for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

3D-SDF for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

PDB for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

3D PDB for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

SMILES for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

INCHI for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

Structure for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

3D Structure for HMDB0059782 (N-Phenylacetyl pyroglutamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra