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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:00:54 UTC

Update Date

2022-03-07 03:17:35 UTC

HMDB ID

HMDB0059732

Secondary Accession Numbers

HMDB59732

Metabolite Identification

Common Name

2-(2-Phenylacetoxy)propionylglycine

Description

2-(2-Phenylacetoxy)propionylglycine 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. 2-(2-Phenylacetoxy)propionylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0059732
     RDKit          3D
2-(2-Phenylacetoxy)propionylglycine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.4408   -0.3362   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082   -1.0397    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -0.2537    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    0.8762    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2553   -0.7065    1.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.0512    1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.6596    1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253   -0.1877    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7829    0.9139   -0.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644   -0.8898    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -0.1507   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -0.3295   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    0.3788   -3.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5591    1.2907   -2.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.4717   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    0.7622   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.3271    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808   -0.0797    3.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    1.0598    3.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208    0.6550   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783   -0.9462   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186   -0.3001   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123   -2.0102   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0768   -1.2760    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -1.6540    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    1.0080    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372   -1.0861    1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512   -1.9065   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.0469   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.2348   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1499    1.8522   -3.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056    2.1912   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    0.9151    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382    1.8867    3.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
M  END


  Mrv0541 02261312002D          

 19 19  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059732

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO5/c1-2-10(15)14-12(13(17)18)19-11(16)8-9-6-4-3-5-7-9/h3-7,12H,2,8H2,1H3,(H,14,15)(H,17,18)

> <INCHI_KEY>
CFIIOIQADIQNGQ-UHFFFAOYSA-N

> <FORMULA>
C13H15NO5

> <MOLECULAR_WEIGHT>
265.2619

> <EXACT_MASS>
265.095022595

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.741551171272427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-phenylacetyl)oxy]-2-propanamidoacetic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.358632436

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.630405976755334

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.323959256374608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.50579711498134

> <JCHEM_POLAR_SURFACE_AREA>
92.69999999999999

> <JCHEM_REFRACTIVITY>
65.14590000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2-phenylacetyl)oxy](propanamido)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059732
     RDKit          3D
2-(2-Phenylacetoxy)propionylglycine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.4408   -0.3362   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082   -1.0397    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -0.2537    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    0.8762    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2553   -0.7065    1.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.0512    1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.6596    1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253   -0.1877    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7829    0.9139   -0.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644   -0.8898    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -0.1507   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -0.3295   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    0.3788   -3.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5591    1.2907   -2.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.4717   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    0.7622   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.3271    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808   -0.0797    3.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    1.0598    3.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208    0.6550   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783   -0.9462   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186   -0.3001   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123   -2.0102   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0768   -1.2760    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -1.6540    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    1.0080    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372   -1.0861    1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512   -1.9065   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.0469   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.2348   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1499    1.8522   -3.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056    2.1912   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    0.9151    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382    1.8867    3.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.002  -9.240   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.671 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.671 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0059732
HETATM    1  C1  UNL     1      -5.441  -0.336  -0.590  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.508  -1.040   0.342  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.292  -0.254   0.625  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.187   0.876   0.068  1.00  0.00           O  
HETATM    5  N1  UNL     1      -2.255  -0.707   1.480  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.071   0.051   1.760  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.115  -0.660   1.412  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.025  -0.188   0.485  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.783   0.914  -0.065  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.264  -0.890   0.096  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.042  -0.151  -0.915  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.855  -0.330  -2.270  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.600   0.379  -3.206  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.559   1.291  -2.818  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.749   1.472  -1.464  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.002   0.762  -0.528  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.000   0.327   3.213  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.881  -0.080   3.982  1.00  0.00           O  
HETATM   19  O5  UNL     1       0.085   1.060   3.709  1.00  0.00           O  
HETATM   20  H1  UNL     1      -5.721   0.655  -0.217  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.378  -0.946  -0.657  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.019  -0.300  -1.626  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.212  -2.010  -0.092  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.077  -1.276   1.270  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.385  -1.654   1.923  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.147   1.008   1.191  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.837  -1.086   1.023  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.951  -1.906  -0.275  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.100  -1.047  -2.597  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.449   0.235  -4.267  1.00  0.00           H  
HETATM   31  H12 UNL     1       5.150   1.852  -3.537  1.00  0.00           H  
HETATM   32  H13 UNL     1       5.506   2.191  -1.161  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.163   0.915   0.529  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.338   1.887   3.175  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4    4    5
CONECT    5    6   25
CONECT    6    7   17   26
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   27   28
CONECT   11   12   12   16
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   33
CONECT   17   18   18   19
CONECT   19   34
END

HMDB0059732
     RDKit          3D
2-(2-Phenylacetoxy)propionylglycine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.4408   -0.3362   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082   -1.0397    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -0.2537    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    0.8762    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2553   -0.7065    1.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.0512    1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.6596    1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253   -0.1877    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7829    0.9139   -0.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644   -0.8898    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -0.1507   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -0.3295   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    0.3788   -3.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5591    1.2907   -2.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    1.4717   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    0.7622   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.3271    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808   -0.0797    3.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    1.0598    3.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208    0.6550   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783   -0.9462   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186   -0.3001   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123   -2.0102   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0768   -1.2760    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -1.6540    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    1.0080    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372   -1.0861    1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512   -1.9065   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.0469   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.2348   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1499    1.8522   -3.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056    2.1912   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    0.9151    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382    1.8867    3.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxypropylidene)amino]-2-[(2-phenylacetyl)oxy]acetate	Generator

Chemical Formula

C₁₃H₁₅NO₅

Average Molecular Weight

265.2619

Monoisotopic Molecular Weight

265.095022595

IUPAC Name

2-[(2-phenylacetyl)oxy]-2-propanamidoacetic acid

Traditional Name

[(2-phenylacetyl)oxy](propanamido)acetic acid

CAS Registry Number

Not Available

SMILES

CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C13H15NO5/c1-2-10(15)14-12(13(17)18)19-11(16)8-9-6-4-3-5-7-9/h3-7,12H,2,8H2,1H3,(H,14,15)(H,17,18)

InChI Key

CFIIOIQADIQNGQ-UHFFFAOYSA-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
Dicarboxylic acid or derivatives
Benzenoid
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid
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

Not Available

Ontology

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	1.16 g/L	ALOGPS
logP	1.35	ALOGPS
logP	1.36	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.15 m³·mol⁻¹	ChemAxon
Polarizability	25.74 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]+	164.473	31661259
DarkChem	[M-H]-	161.459	31661259
DeepCCS	[M+H]+	152.74	30932474
DeepCCS	[M-H]-	150.382	30932474
DeepCCS	[M-2H]-	183.346	30932474
DeepCCS	[M+Na]+	158.834	30932474
AllCCS	[M+H]+	160.0	32859911
AllCCS	[M+H-H2O]+	156.6	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.6	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.	5.06 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1865 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2291.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	518.6 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	631.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1146.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	489.5 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	1545.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	212.2 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	84.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(2-Phenylacetoxy)propionylglycine	CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(O)=O	3412.3	Standard polar	33892256
2-(2-Phenylacetoxy)propionylglycine	CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(O)=O	1937.2	Standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine	CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(O)=O	2136.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(2-Phenylacetoxy)propionylglycine,1TMS,isomer #1	CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2132.2	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,1TMS,isomer #2	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2139.7	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2132.4	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2135.2	Standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2665.4	Standard polar	33892256
2-(2-Phenylacetoxy)propionylglycine,1TBDMS,isomer #1	CCC(=O)NC(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2345.5	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,1TBDMS,isomer #2	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2385.7	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TBDMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2588.6	Semi standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TBDMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2522.0	Standard non polar	33892256
2-(2-Phenylacetoxy)propionylglycine,2TBDMS,isomer #1	CCC(=O)N(C(OC(=O)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2882.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-4223f461609a4d3a9d5c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9100000000-f4fda333a6b767209064	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 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 - 2-(2-Phenylacetoxy)propionylglycine 10V, Positive-QTOF	splash10-014i-5390000000-60be22be6dcd297b30a8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 20V, Positive-QTOF	splash10-05mo-9410000000-a8d84c9e8e0f0e32c3b7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 40V, Positive-QTOF	splash10-0006-9100000000-1f93e946b9c4ef067536	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 10V, Negative-QTOF	splash10-02br-2920000000-72133d9e86a966e9be2e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 20V, Negative-QTOF	splash10-01b9-7910000000-3fd5bee440dc29d9604a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 40V, Negative-QTOF	splash10-00rf-9500000000-50a2dc51cc4d53de99e7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 10V, Positive-QTOF	splash10-014i-6890000000-66f1a03fb4eb9d40960c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 20V, Positive-QTOF	splash10-0006-9500000000-4a654d2b0b84ecad32b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 40V, Positive-QTOF	splash10-0006-9100000000-a0753e3074c1d5f80b6e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 10V, Negative-QTOF	splash10-0udi-1910000000-c21d887019d3f68e04dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 20V, Negative-QTOF	splash10-0006-9300000000-3ac1d4e3dbe17d6da71f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(2-Phenylacetoxy)propionylglycine 40V, Negative-QTOF	splash10-0006-9200000000-f5f02bbcc96b0889338a	2021-09-24	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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Diabetes mellitus type 1	22279428	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Diabetes mellitus type 1	22279428	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 1
van der Kloet FM, Tempels FW, Ismail N, van der Heijden R, Kasper PT, Rojas-Cherto M, van Doorn R, Spijksma G, Koek M, van der Greef J, Makinen VP, Forsblom C, Holthofer H, Groop PH, Reijmers TH, Hankemeier T: Discovery of early-stage biomarkers for diabetic kidney disease using ms-based metabolomics (FinnDiane study). Metabolomics. 2012 Feb;8(1):109-119. Epub 2011 Feb 24. [PubMed:22279428 ]

Associated OMIM IDs

222100 (Diabetes mellitus type 1)

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

124202120

PDB ID

Not Available

ChEBI ID

89911

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 2-(2-Phenylacetoxy)propionylglycine (HMDB0059732)

MOL for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

3D MOL for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

3D SDF for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

3D-SDF for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

PDB for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

3D PDB for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

SMILES for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

INCHI for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

Structure for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

3D Structure for HMDB0059732 (2-(2-Phenylacetoxy)propionylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra