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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:55 UTC

Update Date

2022-09-22 18:34:23 UTC

HMDB ID

HMDB0029156

Secondary Accession Numbers

HMDB0028826
HMDB28826
HMDB29156

Metabolite Identification

Common Name

Glutamylphenylalanine

Description

Glutamylphenylalanine is a dipeptide composed of glutamate and phenylalanine, and is a proteolytic breakdown product of larger proteins. It 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. 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.

Structure

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

HMDB0029156
     RDKit          3D
Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.7176   -2.0011    0.2692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.5623    0.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4401   -0.1131   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -0.6710   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606   -0.2030    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460   -0.7667    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5034    0.9175   -0.0832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    0.0388    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2952    0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.7684    0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -0.1053    0.4909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8607   -0.4033   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    0.2517   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -0.3810   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.2640   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6217    1.5647   -0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    2.2462   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    1.5730   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.5204    1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.3735    2.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179   -0.0044    2.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -2.3456    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561   -2.4480    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948   -0.1934    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.4392   -1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    1.0012   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.2583   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -1.7661   -1.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0404    1.8138    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2420   -1.8027    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    0.9936    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -1.5114   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1154   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.4113    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3852   -0.2310    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5503    2.1240   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    3.2656   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    2.0613   -1.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.9851    2.2649 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
 11 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
M  END

      
  Mrv1652304202022002D          

 21 21  0  0  0  0            999 V2000
 2500.7103 2501.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.7103 2500.2006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4330 2499.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1474 2500.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4330 2498.9762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.7185 2498.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0041 2498.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2896 2498.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5752 2498.9762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2896 2497.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1474 2498.5628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9958 2501.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4247 2501.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1392 2501.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4247 2502.2621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2821 2501.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5677 2501.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8530 2501.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8530 2500.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5676 2499.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2821 2500.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 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
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029156

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
XMBSYZWANAQXEV-QWRGUYRKSA-N

> <FORMULA>
C14H18N2O5

> <MOLECULAR_WEIGHT>
294.307

> <EXACT_MASS>
294.121571688

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.025179342121454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.24

> <JCHEM_LOGP>
-2.383198229413079

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.046167705998164

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.327845682831234

> <JCHEM_PKA_STRONGEST_BASIC>
8.449783585263736

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
73.20410000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutamylphenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029156
     RDKit          3D
Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.7176   -2.0011    0.2692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.5623    0.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4401   -0.1131   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -0.6710   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606   -0.2030    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460   -0.7667    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5034    0.9175   -0.0832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    0.0388    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2952    0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.7684    0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -0.1053    0.4909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8607   -0.4033   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    0.2517   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -0.3810   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.2640   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6217    1.5647   -0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    2.2462   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    1.5730   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.5204    1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.3735    2.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179   -0.0044    2.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -2.3456    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561   -2.4480    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948   -0.1934    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.4392   -1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    1.0012   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.2583   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -1.7661   -1.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0404    1.8138    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2420   -1.8027    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    0.9936    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -1.5114   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1154   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.4113    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3852   -0.2310    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5503    2.1240   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    3.2656   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    2.0613   -1.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.9851    2.2649 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
 11 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    4667.9934668.581   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4667.9934667.041   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4669.3424666.296   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.6754667.064   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4669.3424664.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4668.0084663.984   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4666.6744664.756   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4665.3414663.984   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4664.0074664.756   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4665.3414662.444   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    4670.6754663.984   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    4666.6594669.349   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4669.3264669.349   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4670.6604668.581   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4669.3264670.889   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    4665.3274668.580   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4663.9934669.351   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4662.6594668.580   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4662.6594667.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4663.9934666.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4665.3274667.041   0.000  0.00  0.00           C+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    1   16                                                       
CONECT   13    1   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   17   21   12                                                  
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    HMDB0029156
HETATM    1  N1  UNL     1       2.718  -2.001   0.269  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.777  -0.562   0.253  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.440  -0.113  -1.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.841  -0.671  -1.093  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.661  -0.203   0.053  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.646  -0.767   1.176  1.00  0.00           O  
HETATM    7  O2  UNL     1       6.503   0.918  -0.083  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.422   0.039   0.349  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.370   1.295   0.387  1.00  0.00           O  
HETATM   10  N2  UNL     1       0.265  -0.768   0.395  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.046  -0.105   0.491  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.861  -0.403  -0.730  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.173   0.252  -0.647  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.318  -0.381  -0.151  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.521   0.264  -0.085  1.00  0.00           C  
HETATM   16  C11 UNL     1      -5.622   1.565  -0.514  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.513   2.246  -1.018  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.316   1.573  -1.072  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.699  -0.520   1.748  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.124  -1.374   2.502  1.00  0.00           O  
HETATM   21  O5  UNL     1      -2.918  -0.004   2.128  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.069  -2.346   1.020  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.656  -2.448   0.336  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.395  -0.193   1.119  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.828  -0.439  -1.891  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.443   1.001  -1.029  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.288  -0.258  -2.053  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.853  -1.766  -1.126  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.040   1.814   0.090  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.242  -1.803   0.365  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.850   0.994   0.514  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.998  -1.511  -0.755  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.301  -0.115  -1.645  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.210  -1.411   0.178  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.385  -0.231   0.296  1.00  0.00           H  
HETATM   36  H15 UNL     1      -6.550   2.124  -0.485  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.593   3.266  -1.354  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.436   2.061  -1.455  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.024   0.985   2.265  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3    8   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6    7
CONECT    7   29
CONECT    8    9    9   10
CONECT   10   11   30
CONECT   11   12   19   31
CONECT   12   13   32   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   38
CONECT   19   20   20   21
CONECT   21   39
END

HMDB0029156
     RDKit          3D
Glutamylphenylalanine
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.7176   -2.0011    0.2692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.5623    0.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4401   -0.1131   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -0.6710   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606   -0.2030    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460   -0.7667    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5034    0.9175   -0.0832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    0.0388    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2952    0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.7684    0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -0.1053    0.4909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8607   -0.4033   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    0.2517   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -0.3810   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.2640   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6217    1.5647   -0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    2.2462   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    1.5730   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.5204    1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.3735    2.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179   -0.0044    2.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -2.3456    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561   -2.4480    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948   -0.1934    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.4392   -1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    1.0012   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.2583   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -1.7661   -1.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0404    1.8138    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2420   -1.8027    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    0.9936    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -1.5114   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1154   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.4113    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3852   -0.2310    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5503    2.1240   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    3.2656   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    2.0613   -1.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.9851    2.2649 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
 11 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 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
α-Glu-Phe	HMDB
α-L-Glu-L-Phe	HMDB
α-Glutamylphenylalanine	HMDB
α-L-Glutamyl-L-phenylalanine	HMDB
L-α-Glutamyl-L-phenylalanine	HMDB
N-α-Glutamylphenylalanine	HMDB
N-α-L-Glutamyl-L-phenylalanine	HMDB
N-L-α-Glutamylphenylalanine	HMDB
N-L-α-Glutamyl-L-phenylalanine	HMDB
alpha-Glu-Phe	HMDB
alpha-L-Glu-L-Phe	HMDB
alpha-Glutamylphenylalanine	HMDB
alpha-L-Glutamyl-L-phenylalanine	HMDB
L-alpha-Glutamyl-L-phenylalanine	HMDB
N-alpha-Glutamylphenylalanine	HMDB
N-alpha-L-Glutamyl-L-phenylalanine	HMDB
N-L-alpha-Glutamylphenylalanine	HMDB
N-L-alpha-Glutamyl-L-phenylalanine	HMDB
4-Amino-N-(α-carboxyphenethyl)-glutaramic acid	HMDB
4-Amino-N-(alpha-carboxyphenethyl)-glutaramic acid	HMDB
Glutamylphenylalanine	HMDB
Glu-Phe	HMDB
L-Glu-L-Phe	HMDB
L-Glutamyl-L-phenylalanine	HMDB
N-Glutamylphenylalanine	HMDB
N-L-Glutamyl-L-phenylalanine	HMDB
Glutamyl-phenylalanine	HMDB
Glutamic acid phenylalanine dipeptide	HMDB
Glutamate phenylalanine dipeptide	HMDB
Glutamic acid-phenylalanine dipeptide	HMDB
Glutamate-phenylalanine dipeptide	HMDB
E-F dipeptide	HMDB
EF dipeptide	HMDB
(4S)-4-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]-C-hydroxycarbonimidoyl}butanoate	Generator

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.307

Monoisotopic Molecular Weight

294.121571688

IUPAC Name

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

Traditional Name

glutamylphenylalanine

CAS Registry Number

20556-22-3

SMILES

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

InChI Identifier

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

InChI Key

XMBSYZWANAQXEV-QWRGUYRKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Phenylalanine or derivatives
Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Amino fatty acid
Fatty amide
Dicarboxylic acid or derivatives
N-acyl-amine
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0028826)

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	-2.81	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.4	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	8.45	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	29.03 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
DeepCCS	[M+H]+	166.985	30932474
DeepCCS	[M-H]-	164.627	30932474
DeepCCS	[M-2H]-	197.97	30932474
DeepCCS	[M+Na]+	173.198	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 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.	2.36 minutes	32390414
Predicted by Siyang on May 30, 2022	10.001 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	996.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.3 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	320.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	701.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	679.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	302.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	890.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	369.5 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	234.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutamylphenylalanine	N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	4083.2	Standard polar	33892256
Glutamylphenylalanine	N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2262.1	Standard non polar	33892256
Glutamylphenylalanine	N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2742.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutamylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2611.2	Semi standard non polar	33892256
Glutamylphenylalanine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCC(=O)O	2576.4	Semi standard non polar	33892256
Glutamylphenylalanine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2645.1	Semi standard non polar	33892256
Glutamylphenylalanine,1TMS,isomer #4	C[Si](C)(C)N(C(=O)[C@@H](N)CCC(=O)O)[C@@H](CC1=CC=CC=C1)C(=O)O	2557.0	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2544.0	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2622.4	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #3	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2524.6	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2611.9	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C	2523.0	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #6	C[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2755.7	Semi standard non polar	33892256
Glutamylphenylalanine,2TMS,isomer #7	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2591.0	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2582.9	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2570.6	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2483.5	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2539.9	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2725.8	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2662.6	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2568.9	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2628.7	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2712.5	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2662.5	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2565.2	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2613.3	Standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2687.6	Semi standard non polar	33892256
Glutamylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2704.0	Standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2700.5	Semi standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2688.4	Standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2543.3	Semi standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2636.1	Standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2700.1	Semi standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2736.5	Standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2708.2	Semi standard non polar	33892256
Glutamylphenylalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2716.1	Standard non polar	33892256
Glutamylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2757.0	Semi standard non polar	33892256
Glutamylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2749.9	Standard non polar	33892256
Glutamylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2859.1	Semi standard non polar	33892256
Glutamylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCC(=O)O	2825.7	Semi standard non polar	33892256
Glutamylphenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2850.9	Semi standard non polar	33892256
Glutamylphenylalanine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CCC(=O)O)[C@@H](CC1=CC=CC=C1)C(=O)O	2801.7	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3040.7	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	3073.3	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3038.9	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3042.0	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C(C)(C)C	3027.9	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3194.6	Semi standard non polar	33892256
Glutamylphenylalanine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3051.0	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3245.8	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3118.1	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=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	3228.3	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=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	3099.1	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3447.2	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3172.3	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3280.5	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3134.1	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3421.2	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3163.9	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=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	3261.6	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=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	3120.4	Standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CCC(=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	3400.1	Semi standard non polar	33892256
Glutamylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CCC(=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	3192.2	Standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3618.3	Semi standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3341.3	Standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=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	3429.0	Semi standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=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	3293.2	Standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3616.9	Semi standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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	3371.9	Standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3605.7	Semi standard non polar	33892256
Glutamylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3357.3	Standard non polar	33892256
Glutamylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3790.2	Semi standard non polar	33892256
Glutamylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=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)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3524.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamyl-Phenylalanine 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 - Glutamylphenylalanine 10V, Positive-QTOF	splash10-004j-1290000000-6e7a89e0ccf962fb5e2f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 20V, Positive-QTOF	splash10-0v4r-7950000000-6c8690dfd7caca35021c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 40V, Positive-QTOF	splash10-0a4l-9100000000-a0615d4fefd879e5ecdd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 10V, Negative-QTOF	splash10-0006-0090000000-555568e3635280fb2f88	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 20V, Negative-QTOF	splash10-01r5-1690000000-071b51f05fbd44ebf0ab	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 40V, Negative-QTOF	splash10-024l-6900000000-1519412911f76dca73cd	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 10V, Negative-QTOF	splash10-0006-0690000000-19f7e6715ce7f7db424f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 20V, Negative-QTOF	splash10-0h01-2920000000-d66278578b846b697d72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 40V, Negative-QTOF	splash10-0fr7-8900000000-5047d98ff9fd1a7a96d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 10V, Positive-QTOF	splash10-00r2-0960000000-2006e59b0fce891a1968	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 20V, Positive-QTOF	splash10-0089-9500000000-708d0b33dbe706710bc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylphenylalanine 40V, Positive-QTOF	splash10-0a4i-9200000000-994612eebdd664c996e3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
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
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB112370

KNApSAcK ID

Not Available

Chemspider ID

18724667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18653118

PDB ID

Not Available

ChEBI ID

Not Available

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 Glutamylphenylalanine (HMDB0029156)

MOL for HMDB0029156 (Glutamylphenylalanine)

3D MOL for HMDB0029156 (Glutamylphenylalanine)

3D SDF for HMDB0029156 (Glutamylphenylalanine)

3D-SDF for HMDB0029156 (Glutamylphenylalanine)

PDB for HMDB0029156 (Glutamylphenylalanine)

3D PDB for HMDB0029156 (Glutamylphenylalanine)

SMILES for HMDB0029156 (Glutamylphenylalanine)

INCHI for HMDB0029156 (Glutamylphenylalanine)

Structure for HMDB0029156 (Glutamylphenylalanine)

3D Structure for HMDB0029156 (Glutamylphenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra