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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 18:34:13 UTC

HMDB ID

HMDB0000594

Secondary Accession Numbers

HMDB0029562
HMDB00594
HMDB29562

Metabolite Identification

Common Name

gamma-Glutamylphenylalanine

Description

gamma-Glutamylphenylalanine is a dipeptide composed of gamma-glutamate and phenylalanine, and is a proteolytic breakdown product of larger proteins. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID: 237763 ). gamma-Glutamylphenylalanine belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylphenylalanine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It can be detected in the urine of patients with phenylketonuria, which is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine (Wikipedia). gamma-Glutamylphenylalanine is found in adzuki bean, onion (Allium cepa), garlic (Allium sativum), and soybean.

Structure

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

HMDB0000594
     RDKit          3D
gamma-Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -5.3415    1.5921    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142    0.6600   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7848    0.2185    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478   -0.7405    1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.1398    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.0594    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -0.9339    0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -0.3496   -0.1703 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9623   -0.4817    0.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.0697    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    1.4134    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    1.9001    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    1.0748   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3814   -0.2582   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.7816   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239   -1.0513   -1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -2.0541   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -0.7206   -2.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -0.4845   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -0.5216   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -1.4973   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8318    1.3569    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    2.5217    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3880    1.1992   -0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    1.1781    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -0.1730    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.9621    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8835   -1.7025    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -1.9546    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.7296   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0210    1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -1.5900    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    2.0835    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537    2.9660    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    1.4446   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0930   -0.9433   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -1.8363   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    0.2185   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162   -2.4886   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 21 39  1  0
M  END


  Mrv1652312011717212D          

 21 21  0  0  0  0            999 V2000
 2498.0793 2500.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7941 2499.9236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.7941 2499.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5109 2498.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.2257 2499.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9405 2498.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6552 2499.0982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.3700 2498.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0847 2499.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3700 2497.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6552 2499.9236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5109 2497.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5109 2500.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.2257 2499.9236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5109 2501.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.3649 2499.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.6505 2500.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.9361 2499.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.9360 2499.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.6504 2498.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.3649 2499.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  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
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  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 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000594

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1

> <INCHI_KEY>
XHHOHZPNYFQJKL-QWRGUYRKSA-N

> <FORMULA>
C14H18N2O5

> <MOLECULAR_WEIGHT>
294.3031

> <EXACT_MASS>
294.121571696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.69671745990118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-2.142298981941151

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.933234162481531

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8172405094101052

> <JCHEM_PKA_STRONGEST_BASIC>
9.312071601125322

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
73.20410000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-glutamylphenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000594
     RDKit          3D
gamma-Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -5.3415    1.5921    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142    0.6600   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7848    0.2185    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478   -0.7405    1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.1398    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.0594    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -0.9339    0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -0.3496   -0.1703 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9623   -0.4817    0.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.0697    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    1.4134    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    1.9001    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    1.0748   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3814   -0.2582   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.7816   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239   -1.0513   -1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -2.0541   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -0.7206   -2.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -0.4845   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -0.5216   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -1.4973   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8318    1.3569    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    2.5217    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3880    1.1992   -0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    1.1781    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -0.1730    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.9621    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8835   -1.7025    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -1.9546    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.7296   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0210    1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -1.5900    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    2.0835    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537    2.9660    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    1.4446   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0930   -0.9433   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -1.8363   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    0.2185   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162   -2.4886   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 01-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-DEC-17         0                                  
HETATM    1  C   UNK     0    4663.0814667.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.4164666.524   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4664.4164664.983   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4665.7544664.211   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4667.0884664.983   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4668.4224664.211   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4669.7564664.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4671.0914664.211   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4672.4254664.983   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4671.0914662.671   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    4669.7564666.524   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    4665.7544662.671   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    4665.7544667.293   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4667.0884666.524   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4665.7544668.833   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    4661.7484666.523   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4660.4144667.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4659.0814666.523   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4659.0814664.983   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4660.4144664.213   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4661.7484664.983   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    4                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   17   21    1                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0000594
HETATM    1  N1  UNL     1      -5.342   1.592   0.001  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.214   0.660  -0.227  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.785   0.218   1.142  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.648  -0.741   1.158  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.439  -0.140   0.590  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.417   1.059   0.282  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.290  -0.934   0.391  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.912  -0.350  -0.170  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.962  -0.482   0.928  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.245   0.070   0.498  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.527   1.413   0.679  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.738   1.900   0.280  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.668   1.075  -0.293  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.381  -0.258  -0.470  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.178  -0.782  -0.082  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.324  -1.051  -1.388  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.625  -2.054  -1.760  1.00  0.00           O  
HETATM   18  O3  UNL     1       2.411  -0.721  -2.178  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.672  -0.484  -1.053  1.00  0.00           C  
HETATM   20  O4  UNL     1      -5.875  -0.522  -1.396  1.00  0.00           O  
HETATM   21  O5  UNL     1      -3.834  -1.497  -1.455  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.832   1.357   0.895  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.896   2.522   0.134  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.388   1.199  -0.716  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.539   1.178   1.692  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.673  -0.173   1.700  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.446  -0.962   2.258  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.884  -1.703   0.651  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.237  -1.955   0.628  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.685   0.730  -0.362  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.580  -0.021   1.856  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.051  -1.590   1.118  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.826   2.083   1.122  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.954   2.966   0.427  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.637   1.445  -0.617  1.00  0.00           H  
HETATM   36  H15 UNL     1       6.093  -0.943  -0.920  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.946  -1.836  -0.215  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.683   0.218  -2.400  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.016  -2.489  -1.318  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3   19   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6    7
CONECT    7    8   29
CONECT    8    9   16   30
CONECT    9   10   31   32
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   37
CONECT   16   17   17   18
CONECT   18   38
CONECT   19   20   20   21
CONECT   21   39
END

HMDB0000594
     RDKit          3D
gamma-Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -5.3415    1.5921    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142    0.6600   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7848    0.2185    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478   -0.7405    1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.1398    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.0594    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -0.9339    0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -0.3496   -0.1703 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9623   -0.4817    0.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.0697    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    1.4134    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    1.9001    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    1.0748   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3814   -0.2582   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.7816   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239   -1.0513   -1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -2.0541   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -0.7206   -2.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -0.4845   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -0.5216   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -1.4973   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8318    1.3569    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    2.5217    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3880    1.1992   -0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    1.1781    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -0.1730    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.9621    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8835   -1.7025    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -1.9546    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.7296   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0210    1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -1.5900    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    2.0835    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537    2.9660    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    1.4446   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0930   -0.9433   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -1.8363   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    0.2185   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162   -2.4886   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 21 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid	ChEBI
L-gamma-Glu-L-phe	ChEBI
L-gamma-Glutamyl-L-phenylalanine	ChEBI
N-(gamma-L-Glutamyl)phenylalanine	ChEBI
N-L-gamma-Glutamyl-3-phenyl-L-alanine	ChEBI
N-L-gamma-Glutamyl-L-phenylalanine	ChEBI
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate	Generator
L-g-Glu-L-phe	Generator
L-Γ-glu-L-phe	Generator
L-g-Glutamyl-L-phenylalanine	Generator
L-Γ-glutamyl-L-phenylalanine	Generator
N-(g-L-Glutamyl)phenylalanine	Generator
N-(Γ-L-glutamyl)phenylalanine	Generator
N-L-g-Glutamyl-3-phenyl-L-alanine	Generator
N-L-Γ-glutamyl-3-phenyl-L-alanine	Generator
N-L-g-Glutamyl-L-phenylalanine	Generator
N-L-Γ-glutamyl-L-phenylalanine	Generator
g-Glutamylphenylalanine	Generator
Γ-glutamylphenylalanine	Generator
gamma-Glu-phe	MeSH
γ-Glu-Phe	HMDB, Generator
γ-L-Glu-L-Phe	HMDB
γ-L-Glutamyl-L-phenylalanine	HMDB
N-γ-Glutamylphenylalanine	HMDB
N-L-γ-Glutamylphenylalanine	HMDB
gamma-L-Glu-L-Phe	HMDB
gamma-L-Glutamyl-L-phenylalanine	HMDB
N-gamma-Glutamylphenylalanine	HMDB
N-L-gamma-Glutamylphenylalanine	HMDB
H-γ-Glu-Phe-OH	HMDB
H-gamma-Glu-Phe-OH	HMDB
gamma-Glutamylphenylalanine	HMDB, ChEBI
N-gamma-L-Glutamyl-L-phenylalanine	HMDB
N-γ-L-Glutamyl-L-phenylalanine	HMDB
g-Glu-Phe	Generator, HMDB

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.3031

Monoisotopic Molecular Weight

294.121571696

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid

Traditional Name

gamma-glutamylphenylalanine

CAS Registry Number

7432-24-8

SMILES

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

InChI Identifier

InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1

InChI Key

XHHOHZPNYFQJKL-QWRGUYRKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0000594)
Placenta (HMDB: HMDB0000594)

Excreta

Biofluid or Excreta

Urine (PMID: 466810)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0000594)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.61 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	73.2 m³·mol⁻¹	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	167.958	31661259
DarkChem	[M-H]-	165.328	31661259
AllCCS	[M+H]+	166.824	32859911
AllCCS	[M-H]-	167.651	32859911
DeepCCS	[M+H]+	166.325	30932474
DeepCCS	[M-H]-	163.967	30932474
DeepCCS	[M-2H]-	197.373	30932474
DeepCCS	[M+Na]+	172.6	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.8	32859911
AllCCS	[M+NH4]+	169.7	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	168.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamylphenylalanine	N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	3911.4	Standard polar	33892256
gamma-Glutamylphenylalanine	N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	2430.4	Standard non polar	33892256
gamma-Glutamylphenylalanine	N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	2867.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@H](N)C(=O)O	2607.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2598.1	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O	2678.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TMS,isomer #4	C[Si](C)(C)N(C(=O)CC[C@H](N)C(=O)O)[C@@H](CC1=CC=CC=C1)C(=O)O	2609.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2547.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O	2648.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C	2551.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O[Si](C)(C)C	2643.2	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2553.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #6	C[Si](C)(C)N([C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O)[Si](C)(C)C	2754.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TMS,isomer #7	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)C(=O)O	2624.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2590.9	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2594.7	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3193.1	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2499.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2564.2	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3558.6	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2727.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2684.4	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3323.9	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O	2593.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O	2609.4	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O	3325.7	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2747.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2648.8	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3354.0	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2581.1	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2637.7	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3288.6	Standard polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2668.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2722.0	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3440.7	Standard polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2728.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2687.2	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3055.2	Standard polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2557.4	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2642.7	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3013.5	Standard polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2677.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2738.6	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3160.8	Standard polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2703.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2733.3	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3157.0	Standard polar	33892256
gamma-Glutamylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2751.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2750.9	Standard non polar	33892256
gamma-Glutamylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2934.0	Standard polar	33892256
gamma-Glutamylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@H](N)C(=O)O	2873.1	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2854.0	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O	2891.6	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](N)C(=O)O)[C@@H](CC1=CC=CC=C1)C(=O)O	2850.9	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3049.6	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3091.0	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	3048.6	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3098.5	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3052.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3212.2	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O	3091.1	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3263.8	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3140.7	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3448.0	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3229.1	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3129.1	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3694.7	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3435.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3194.7	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3504.4	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3283.0	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3139.6	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3540.7	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3455.0	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3171.6	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3526.6	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3280.2	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3144.5	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3513.1	Standard polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3409.3	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3207.1	Standard non polar	33892256
gamma-Glutamylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3584.2	Standard polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3624.8	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3353.8	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3361.0	Standard polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3431.7	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3308.1	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3371.5	Standard polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3607.8	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3381.8	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3430.4	Standard polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3620.8	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3373.9	Standard non polar	33892256
gamma-Glutamylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3426.1	Standard polar	33892256
gamma-Glutamylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3777.8	Semi standard non polar	33892256
gamma-Glutamylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3528.4	Standard non polar	33892256
gamma-Glutamylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3339.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9350000000-cee136a59eda9bbc48b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9633100000-04cb3c5e9af1918fedf0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylphenylalanine GC-MS (TBDMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Glutamylphenylalanine LC-ESI-IT , positive-QTOF	splash10-014i-0900000000-3c15b0ec8b0aa7b4f562	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 10V, Positive-QTOF	splash10-01ot-1490000000-8a194f7de818cb11e47b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 20V, Positive-QTOF	splash10-03xs-2960000000-8471d66cf80c273476e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 40V, Positive-QTOF	splash10-0006-9200000000-cee53e3b344fef2f519e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 10V, Negative-QTOF	splash10-0006-0290000000-f75848c2ae5c1246f8d8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 20V, Negative-QTOF	splash10-0035-1790000000-fd452e6dee821306584b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 40V, Negative-QTOF	splash10-02fx-9500000000-9ba84b5fd475503d8cd7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 10V, Negative-QTOF	splash10-01tc-0980000000-3d8a781a1b7c5419cc5c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 20V, Negative-QTOF	splash10-0imm-2930000000-ee52208f821d132b59a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 40V, Negative-QTOF	splash10-006x-9800000000-49bcc3238b9451889ddf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 10V, Positive-QTOF	splash10-0002-1790000000-683c9d45013f9557d41c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 20V, Positive-QTOF	splash10-00di-2910000000-d284cbb0231807781a10	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylphenylalanine 40V, Positive-QTOF	splash10-0ac0-9400000000-939d577cffe7458ad422	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	43.00 (8.00-78.00) umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	466810	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Phenylketonuria
Peck H, Pollitt RJ: The occurrence of gamma-glutamylphenylalanine in the urine of newborn phenylketonurics. Clin Chim Acta. 1979 Jun 15;94(3):237-40. [PubMed:466810 ]

Associated OMIM IDs

114500 (Colorectal cancer)
261600 (Phenylketonuria)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112161

KNApSAcK ID

Not Available

Chemspider ID

99868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

111299

PDB ID

Not Available

ChEBI ID

89582

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bodnaryk, Robert P. Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine. Insect Biochemistry (1972), 2(1), 49-52.

Material Safety Data Sheet (MSDS)

Not Available

General References

Peck H, Pollitt RJ: The occurrence of gamma-glutamylphenylalanine in the urine of newborn phenylketonurics. Clin Chim Acta. 1979 Jun 15;94(3):237-40. [PubMed:466810 ]
Bridges RJ, Meister A: gamma-Glutamyl amino acids. Transport and conversion to 5-oxoproline in the kidney. J Biol Chem. 1985 Jun 25;260(12):7304-8. [PubMed:3997870 ]
Orlowski M, Wilk S: Intermediates of the gamma-glutamyl cycle in mouse tissues. Influence of administration of amino acids on pyrrolidone carboxylate and gamma-glutamyl amino acids. Eur J Biochem. 1975 May 6;53(2):581-90. [PubMed:237763 ]
Kamerling JP, Aarsen GJ, Duran M, de Bree PK, van Sprang FJ, Wadman SK: Chromatographic determination and mass spectrometric identification of gamma-glutamylphenylalanine, a urinary constituent in phenylketonuria. Clin Chim Acta. 1980 Mar 28;102(2-3):137-45. [PubMed:7371187 ]
Lawson LD, Gardner CD: Composition, stability, and bioavailability of garlic products used in a clinical trial. J Agric Food Chem. 2005 Aug 10;53(16):6254-61. [PubMed:16076102 ]
Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for gamma-Glutamylphenylalanine (HMDB0000594)

MOL for HMDB0000594 (gamma-Glutamylphenylalanine)

3D MOL for HMDB0000594 (gamma-Glutamylphenylalanine)

3D SDF for HMDB0000594 (gamma-Glutamylphenylalanine)

3D-SDF for HMDB0000594 (gamma-Glutamylphenylalanine)

PDB for HMDB0000594 (gamma-Glutamylphenylalanine)

3D PDB for HMDB0000594 (gamma-Glutamylphenylalanine)

SMILES for HMDB0000594 (gamma-Glutamylphenylalanine)

INCHI for HMDB0000594 (gamma-Glutamylphenylalanine)

Structure for HMDB0000594 (gamma-Glutamylphenylalanine)

3D Structure for HMDB0000594 (gamma-Glutamylphenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra