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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:23:42 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060478

Secondary Accession Numbers

HMDB60478

Metabolite Identification

Common Name

gamma-Glutamyl-beta-cyanoalanine

Description

gamma-Glutamyl-beta-cyanoalanine, also known as γ-glutamyl-β-cyanoalanine, 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. gamma-Glutamyl-beta-cyanoalanine is a very strong basic compound (based on its pKa). These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Structure

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

HMDB0060478
     RDKit          3D
gamma-Glutamyl-beta-cyanoalanine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4129   -2.3740    2.1352 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.6193    1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -0.6653    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.5945    0.5519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5366    0.2875    0.7805 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.1918   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -0.5182   -1.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.4286    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.3602   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877    0.0169    0.2871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2850   -1.4115    0.1463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    0.7987   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874    2.0443   -0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.1404   -1.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    1.7096   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    2.3705   -0.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    2.0237   -0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -1.1082   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6953   -0.4567   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9125    1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -1.4627   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -1.5130    0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614   -0.2091    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    0.0699   -1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143    1.4398   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2206    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -1.7480    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871   -1.6849   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0892   -0.0162   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    2.4185    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
M  END


  Mrv0541 05161318232D          

 17 16  0  0  0  0            999 V2000
    3.3809    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    4.4270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.8395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  3  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  6  0  0  0
 12  7  2  0  0  0  0
  7 13  1  4  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060478

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)/t5-,6-/m0/s1

> <INCHI_KEY>
QUAADUAOVLZBJM-WDSKDSINSA-N

> <FORMULA>
C9H13N3O5

> <MOLECULAR_WEIGHT>
243.2166

> <EXACT_MASS>
243.085520541

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
22.49163557929082

> <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-cyanoethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <ALOGPS_LOGP>
-3.14

> <JCHEM_LOGP>
-3.710025442217001

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.3598852924341847

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3562283540532833

> <JCHEM_PKA_STRONGEST_BASIC>
9.537515643281333

> <JCHEM_POLAR_SURFACE_AREA>
157

> <JCHEM_REFRACTIVITY>
54.121500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-cyanoethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060478
     RDKit          3D
gamma-Glutamyl-beta-cyanoalanine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4129   -2.3740    2.1352 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.6193    1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -0.6653    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.5945    0.5519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5366    0.2875    0.7805 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.1918   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -0.5182   -1.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.4286    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.3602   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877    0.0169    0.2871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2850   -1.4115    0.1463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    0.7987   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874    2.0443   -0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.1404   -1.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    1.7096   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    2.3705   -0.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    2.0237   -0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -1.1082   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6953   -0.4567   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9125    1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -1.4627   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -1.5130    0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614   -0.2091    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    0.0699   -1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143    1.4398   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2206    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -1.7480    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871   -1.6849   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0892   -0.0162   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    2.4185    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       6.311   6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   8.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   9.034   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.310  -1.746   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.977   9.034   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.645  10.574   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.978   8.264   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3   10                                                       
CONECT    5    1    8   11                                                  
CONECT    6    3    9   12                                                  
CONECT    7    2   12   13                                                  
CONECT    8    5   14   15                                                  
CONECT    9    6   16   17                                                  
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6    7                                                       
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0060478
HETATM    1  N1  UNL     1       3.413  -2.374   2.135  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.507  -1.619   1.260  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.636  -0.665   0.157  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.894   0.594   0.552  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.537   0.288   0.780  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.681  -0.192  -0.013  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.963  -0.518  -1.340  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.700  -0.429   0.467  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.723   0.360  -0.318  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.088   0.017   0.287  1.00  0.00           C  
HETATM   11  N3  UNL     1      -3.285  -1.412   0.146  1.00  0.00           N  
HETATM   12  C8  UNL     1      -4.148   0.799  -0.367  1.00  0.00           C  
HETATM   13  O2  UNL     1      -4.087   2.044  -0.314  1.00  0.00           O  
HETATM   14  O3  UNL     1      -5.193   0.140  -1.029  1.00  0.00           O  
HETATM   15  C9  UNL     1       3.137   1.710  -0.385  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.265   2.371  -0.964  1.00  0.00           O  
HETATM   17  O5  UNL     1       4.490   2.024  -0.620  1.00  0.00           O  
HETATM   18  H1  UNL     1       3.141  -1.108  -0.729  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.695  -0.457  -0.097  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.348   0.912   1.536  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.966  -1.463  -1.683  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.988  -1.513   0.362  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.761  -0.209   1.541  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.721   0.070  -1.376  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.514   1.440  -0.215  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.039   0.221   1.380  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.130  -1.748   0.628  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.287  -1.685  -0.859  1.00  0.00           H  
HETATM   29  H12 UNL     1      -6.089  -0.016  -0.615  1.00  0.00           H  
HETATM   30  H13 UNL     1       5.083   2.418   0.083  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   18   19
CONECT    4    5   15   20
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27   28
CONECT   12   13   13   14
CONECT   14   29
CONECT   15   16   16   17
CONECT   17   30
END

HMDB0060478
     RDKit          3D
gamma-Glutamyl-beta-cyanoalanine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4129   -2.3740    2.1352 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.6193    1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -0.6653    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.5945    0.5519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5366    0.2875    0.7805 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.1918   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -0.5182   -1.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.4286    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.3602   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877    0.0169    0.2871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2850   -1.4115    0.1463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    0.7987   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874    2.0443   -0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.1404   -1.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    1.7096   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    2.3705   -0.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    2.0237   -0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -1.1082   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6953   -0.4567   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9125    1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -1.4627   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -1.5130    0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614   -0.2091    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    0.0699   -1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143    1.4398   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2206    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -1.7480    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871   -1.6849   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0892   -0.0162   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    2.4185    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
g-Glutamyl-b-cyanoalanine	Generator
Γ-glutamyl-β-cyanoalanine	Generator

Chemical Formula

C₉H₁₃N₃O₅

Average Molecular Weight

243.2166

Monoisotopic Molecular Weight

243.085520541

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-cyanoethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-cyanoethyl]-C-hydroxycarbonimidoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)/t5-,6-/m0/s1

InChI Key

QUAADUAOVLZBJM-WDSKDSINSA-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
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Nitrile
Carbonitrile
Carboxylic acid
Hydrocarbon derivative
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Primary amine
Organonitrogen compound
Amine
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:10565 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060478)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.96 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	157 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.12 m³·mol⁻¹	ChemAxon
Polarizability	22.49 Å³	ChemAxon
Number of Rings	0	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]+	158.167	31661259
DarkChem	[M-H]-	153.238	31661259
DeepCCS	[M+H]+	153.527	30932474
DeepCCS	[M-H]-	151.169	30932474
DeepCCS	[M-2H]-	184.171	30932474
DeepCCS	[M+Na]+	159.621	30932474
AllCCS	[M+H]+	152.3	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	155.3	32859911
AllCCS	[M+Na]+	156.1	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	151.9	32859911
AllCCS	[M+HCOO]-	152.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.19 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8697 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	411.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	42.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	289.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	237.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	837.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	576.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	43.1 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	717.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	678.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.7 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	467.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-beta-cyanoalanine	N[C@@H](CCC(O)=N[C@@H](CC#N)C(O)=O)C(O)=O	2655.9	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine	N[C@@H](CCC(O)=N[C@@H](CC#N)C(O)=O)C(O)=O	1988.1	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine	N[C@@H](CCC(O)=N[C@@H](CC#N)C(O)=O)C(O)=O	2500.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-beta-cyanoalanine,1TMS,isomer #1	C[Si](C)(C)OC(CC[C@H](N)C(=O)O)=N[C@@H](CC#N)C(=O)O	2315.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@H](N)C(=O)O	2294.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=N[C@@H](CC#N)C(=O)O	2288.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TMS,isomer #4	C[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O	2356.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C	2264.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@H](N)C(=O)O)O[Si](C)(C)C	2278.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C)C(=O)O	2330.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C	2210.4	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)C(=O)O	2295.1	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O[Si](C)(C)C	2305.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TMS,isomer #7	C[Si](C)(C)N([C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O)[Si](C)(C)C	2419.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2221.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2295.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	2308.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #4	C[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=N[C@@H](CC#N)C(=O)O	2438.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2254.1	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2381.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H](CCC(O)=N[C@@H](CC#N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2408.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2250.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2284.1	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2930.5	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2442.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2346.5	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3143.2	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2427.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2369.6	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3072.6	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2388.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2337.1	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3125.8	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2428.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2377.8	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2743.0	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC[C@H](N)C(=O)O)=N[C@@H](CC#N)C(=O)O	2510.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@H](N)C(=O)O	2503.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=N[C@@H](CC#N)C(=O)O	2498.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O	2548.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C	2644.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C	2667.4	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C)C(=O)O	2717.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C	2625.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2681.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2698.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2805.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2827.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2878.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O	2898.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N[C@@H](CC#N)C(=O)O	3019.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2856.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3002.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(O)=N[C@@H](CC#N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3041.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3048.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2958.6	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=N[C@@H](CC#N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3193.0	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3242.1	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3004.1	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=N[C@@H](CC#N)C(=O)O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3304.9	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3237.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3031.9	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3246.6	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)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	3229.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)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	3058.1	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)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	3330.1	Standard polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(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)O[Si](C)(C)C(C)(C)C	3450.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(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)O[Si](C)(C)C(C)(C)C	3167.4	Standard non polar	33892256
gamma-Glutamyl-beta-cyanoalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC#N)N=C(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)O[Si](C)(C)C(C)(C)C	3120.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-cyanoalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6y-9500000000-85b76c836d9845c482a3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-cyanoalanine GC-MS (3 TMS) - 70eV, Positive	splash10-0006-3129100000-043ad9f012fd11656aba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 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 - gamma-Glutamyl-beta-cyanoalanine 10V, Positive-QTOF	splash10-01ta-1960000000-6e66795d1179cc4cdce7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 20V, Positive-QTOF	splash10-03yj-5910000000-92dce90adec9fe6fadca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 40V, Positive-QTOF	splash10-05mo-9300000000-4a0506e21080dd49eb1b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 10V, Negative-QTOF	splash10-006x-0490000000-bc3a56452e83c180c084	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 20V, Negative-QTOF	splash10-01zd-2940000000-161c367bd69d2799c9b2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 40V, Negative-QTOF	splash10-0006-9200000000-36c4d7accf3a1cebe332	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 10V, Positive-QTOF	splash10-002f-2590000000-f47a2e64287eded7ad72	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 20V, Positive-QTOF	splash10-014s-7920000000-822485c7256aa5ce3718	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 40V, Positive-QTOF	splash10-052r-9100000000-1d8efe4066032e19ea6f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 10V, Negative-QTOF	splash10-00ed-2790000000-6bc11039346e3920554a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 20V, Negative-QTOF	splash10-01za-2930000000-77ee3460fe90ad575435	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-cyanoalanine 40V, Negative-QTOF	splash10-00kf-9200000000-3d10ac309d0fec7cadb2	2021-10-12	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

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05711

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53297342

PDB ID

Not Available

ChEBI ID

10565

Food Biomarker Ontology

Not Available

VMH ID

HC01577

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Gamma-glutamyltranspeptidase 1

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:: GGT1
Uniprot ID:: P19440
Molecular weight:: 61409.67

Reactions

L-3-Cyanoalanine + Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Water	details

Enzyme Details

2. Gamma-glutamyltransferase 7

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT7
Uniprot ID:: Q9UJ14
Molecular weight:: 70466.015

Reactions

L-3-Cyanoalanine + Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Water	details

Enzyme Details

3. Gamma-glutamyltransferase 6

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT6
Uniprot ID:: Q6P531
Molecular weight:: 50508.83

Reactions

L-3-Cyanoalanine + Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Water	details

Enzyme Details

4. Gamma-glutamyltransferase 5

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:: GGT5
Uniprot ID:: P36269
Molecular weight:: 62331.75

Reactions

L-3-Cyanoalanine + Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Water	details

Showing metabocard for gamma-Glutamyl-beta-cyanoalanine (HMDB0060478)

MOL for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

3D MOL for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

3D SDF for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

3D-SDF for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

PDB for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

3D PDB for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

SMILES for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

INCHI for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

Structure for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

3D Structure for HMDB0060478 (gamma-Glutamyl-beta-cyanoalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions