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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-03-03 11:17:37 UTC

Update Date

2021-09-14 15:41:42 UTC

HMDB ID

HMDB0011738

Secondary Accession Numbers

HMDB11738

Metabolite Identification

Common Name

N2-gamma-Glutamylglutamine

Description

N2-gamma-Glutamylglutamine, also known as gamma-L-Glu-L-Gln or L-gamma-glutamyl-L-glutamine, 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. N2-gamma-Glutamylglutamine is a very strong basic compound (based on its pKa). N2-gamma-Glutamylglutamine is a dipeptide obtained from the condensation of the gamma-carboxy group of glutamic acid with the alpha-amino group of glutamine. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

      
  Mrv1652312131723092D          

 19 18  0  0  0  0            999 V2000
 2499.2845 2500.4135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2499.2845 2499.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7134 2499.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4299 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1443 2499.5885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.8588 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5732 2499.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8588 2498.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1443 2500.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2498.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5700 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8556 2500.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1411 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.4266 2500.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1411 2501.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7134 2500.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2501.6500    0.0000 O   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 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011738

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N3O6/c11-5(9(16)17)1-4-8(15)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1

> <INCHI_KEY>
JBFYFLXEJFQWMU-WDSKDSINSA-N

> <FORMULA>
C10H17N3O6

> <MOLECULAR_WEIGHT>
275.2585

> <EXACT_MASS>
275.111735291

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.116888296370377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid

> <ALOGPS_LOGP>
-3.56

> <JCHEM_LOGP>
-4.984023558115107

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.7650402379809544

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9339452893798104

> <JCHEM_PKA_STRONGEST_BASIC>
9.312071937916727

> <JCHEM_POLAR_SURFACE_AREA>
172.81

> <JCHEM_REFRACTIVITY>
61.19770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/N%5BC@@H%5D(CCC(=O)N%5BC@@H%5D(...
 OpenBabel09142113233D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:35})
 36 35  0  0  0  0  0  0  0  0999 V2000
    4.1953    0.0257    1.8257 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9797   -0.7377    0.5893 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7491   -1.7737    0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -0.1279   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5219   -0.2895    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723    0.3111   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.8185   -1.2355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713    0.2845    0.3680 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890    0.8683   -0.3779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8376    0.7064   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.2035    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -1.2743   -0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -1.9291    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -3.2383   -0.1529 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -1.2779    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604    2.3477   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    3.0944   -0.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599    2.8616    0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -0.6892   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -1.6105   -1.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0470    0.1792   -0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108    0.9902    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965   -0.0448    2.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038    0.9314   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090   -0.6378   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.3488    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253    0.2204    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.1213    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035    0.2886    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1358    0.6978   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660   -1.3593   -1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -1.7684    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -3.7591   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945   -3.6598    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191    4.0386   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -1.5383   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  2 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 28  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 35  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 36  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 13-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-DEC-17         0                                  
HETATM    1  C   UNK     0    4665.3314667.439   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4665.3314665.899   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4666.6654665.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4667.9984665.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4669.3364665.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.6694665.899   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4672.0034665.126   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4673.3374665.899   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4672.0034663.586   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4670.6694667.439   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4666.6654663.586   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4663.9974668.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4662.6644667.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4661.3304668.207   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    4659.9964667.439   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0    4661.3304669.747   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    4666.6654668.207   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    4667.9984667.439   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    4666.6654669.747   0.000  0.00  0.00           O+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    1   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/N%5BC@@H%5D(CCC(=O)N%5BC@@H%5D(... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNK     1       4.195   0.026   1.826  1.00  0.00           N  
HETATM    2  C   UNK     1       3.980  -0.738   0.589  1.00  0.00           C  
HETATM    3  H   UNK     1       3.749  -1.774   0.838  1.00  0.00           H  
HETATM    4  C   UNK     1       2.812  -0.128  -0.190  1.00  0.00           C  
HETATM    5  C   UNK     1       1.522  -0.289   0.616  1.00  0.00           C  
HETATM    6  C   UNK     1       0.372   0.311  -0.151  1.00  0.00           C  
HETATM    7  O   UNK     1       0.566   0.819  -1.236  1.00  0.00           O  
HETATM    8  N   UNK     1      -0.871   0.284   0.368  1.00  0.00           N  
HETATM    9  C   UNK     1      -1.989   0.868  -0.378  1.00  0.00           C  
HETATM   10  H   UNK     1      -1.838   0.706  -1.445  1.00  0.00           H  
HETATM   11  C   UNK     1      -3.296   0.203   0.059  1.00  0.00           C  
HETATM   12  C   UNK     1      -3.273  -1.274  -0.337  1.00  0.00           C  
HETATM   13  C   UNK     1      -4.561  -1.929   0.093  1.00  0.00           C  
HETATM   14  N   UNK     1      -4.766  -3.238  -0.153  1.00  0.00           N  
HETATM   15  O   UNK     1      -5.413  -1.278   0.660  1.00  0.00           O  
HETATM   16  C   UNK     1      -2.060   2.348  -0.100  1.00  0.00           C  
HETATM   17  O   UNK     1      -3.013   3.094  -0.679  1.00  0.00           O  
HETATM   18  O   UNK     1      -1.260   2.862   0.645  1.00  0.00           O  
HETATM   19  C   UNK     1       5.227  -0.689  -0.255  1.00  0.00           C  
HETATM   20  O   UNK     1       5.427  -1.611  -1.210  1.00  0.00           O  
HETATM   21  O   UNK     1       6.047   0.179  -0.072  1.00  0.00           O  
HETATM   22  H   UNK     1       4.411   0.990   1.622  1.00  0.00           H  
HETATM   23  H   UNK     1       3.397  -0.045   2.438  1.00  0.00           H  
HETATM   24  H   UNK     1       3.004   0.931  -0.361  1.00  0.00           H  
HETATM   25  H   UNK     1       2.709  -0.638  -1.147  1.00  0.00           H  
HETATM   26  H   UNK     1       1.331  -1.349   0.787  1.00  0.00           H  
HETATM   27  H   UNK     1       1.625   0.220   1.574  1.00  0.00           H  
HETATM   28  H   UNK     1      -1.026  -0.121   1.235  1.00  0.00           H  
HETATM   29  H   UNK     1      -3.404   0.289   1.140  1.00  0.00           H  
HETATM   30  H   UNK     1      -4.136   0.698  -0.430  1.00  0.00           H  
HETATM   31  H   UNK     1      -3.166  -1.359  -1.419  1.00  0.00           H  
HETATM   32  H   UNK     1      -2.434  -1.768   0.151  1.00  0.00           H  
HETATM   33  H   UNK     1      -4.085  -3.759  -0.606  1.00  0.00           H  
HETATM   34  H   UNK     1      -5.595  -3.660   0.124  1.00  0.00           H  
HETATM   35  H   UNK     1      -3.019   4.039  -0.470  1.00  0.00           H  
HETATM   36  H   UNK     1       6.242  -1.538  -1.726  1.00  0.00           H  
CONECT    1    2   22   23                                            
CONECT    2    1    3    4   19                                       
CONECT    3    2                                                      
CONECT    4    2    5   24   25                                       
CONECT    5    4    6   26   27                                       
CONECT    6    5    7    7    8                                       
CONECT    7    6    6                                                 
CONECT    8    6    9   28                                            
CONECT    9    8   10   11   16                                       
CONECT   10    9                                                      
CONECT   11    9   12   29   30                                       
CONECT   12   11   13   31   32                                       
CONECT   13   12   14   15   15                                       
CONECT   14   13   33   34                                            
CONECT   15   13   13                                                 
CONECT   16    9   17   18   18                                       
CONECT   17   16   35                                                 
CONECT   18   16   16                                                 
CONECT   19    2   20   21   21                                       
CONECT   20   19   36                                                 
CONECT   21   19   19                                                 
CONECT   22    1                                                      
CONECT   23    1                                                      
CONECT   24    4                                                      
CONECT   25    4                                                      
CONECT   26    5                                                      
CONECT   27    5                                                      
CONECT   28    8                                                      
CONECT   29   11                                                      
CONECT   30   11                                                      
CONECT   31   12                                                      
CONECT   32   12                                                      
CONECT   33   14                                                      
CONECT   34   14                                                      
CONECT   35   17                                                      
CONECT   36   20                                                      
MASTER        0    0    0    0    0    0    0    0   36    0   36    0
END

https://cactus.nci.nih.gov/chemical/structure/N%5BC@@H%5D(CCC(=O)N%5BC@@H%5D(...
 OpenBabel09142113233D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:35})
 36 35  0  0  0  0  0  0  0  0999 V2000
    4.1953    0.0257    1.8257 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9797   -0.7377    0.5893 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7491   -1.7737    0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -0.1279   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5219   -0.2895    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723    0.3111   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.8185   -1.2355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713    0.2845    0.3680 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890    0.8683   -0.3779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8376    0.7064   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.2035    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -1.2743   -0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -1.9291    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -3.2383   -0.1529 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -1.2779    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604    2.3477   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    3.0944   -0.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599    2.8616    0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -0.6892   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -1.6105   -1.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0470    0.1792   -0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108    0.9902    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965   -0.0448    2.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038    0.9314   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090   -0.6378   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.3488    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253    0.2204    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.1213    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035    0.2886    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1358    0.6978   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660   -1.3593   -1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -1.7684    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -3.7591   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945   -3.6598    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191    4.0386   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -1.5383   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  2 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 28  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 35  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 36  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
gamma-L-Glu-L-GLN	ChEBI
g-L-Glu-L-GLN	Generator
Γ-L-glu-L-GLN	Generator
N2-g-Glutamylglutamine	Generator
N2-Γ-glutamylglutamine	Generator
Γ-glu-GLN	HMDB
Γ-glutamylglutamine	HMDB
Γ-L-glutamyl-L-glutamine	HMDB
L-Γ-glutamyl-L-glutamine	HMDB
N2-L-Γ-glutamylglutamine	HMDB
N2-L-Γ-glutamyl-L-glutamine	HMDB
gamma-Glu-GLN	HMDB
gamma-Glutamylglutamine	HMDB
gamma-L-Glutamyl-L-glutamine	HMDB
L-gamma-Glutamyl-L-glutamine	HMDB
N2-L-gamma-Glutamylglutamine	HMDB
N2-L-gamma-Glutamyl-L-glutamine	HMDB
g-Glutamyl glutamine	HMDB
Γ-glutamyl glutamine	HMDB
g-Glu-GLN	HMDB
g-Glutamylglutamine	HMDB
N2-gamma-Glutamylglutamine	HMDB

Chemical Formula

C₁₀H₁₇N₃O₆

Average Molecular Weight

275.2585

Monoisotopic Molecular Weight

275.111735291

IUPAC Name

(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid

Traditional Name

(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid

CAS Registry Number

10148-81-9

SMILES

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

InChI Identifier

InChI=1S/C10H17N3O6/c11-5(9(16)17)1-4-8(15)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73707 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Organ and components:

Prostate

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

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.17 g/L	ALOGPS
logP	-3.6	ALOGPS
logP	-5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.81 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	61.2 m³·mol⁻¹	ChemAxon
Polarizability	26.12 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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	164.912	31661259
DarkChem	[M-H]-	Predicted	Not Available	161.731	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
N2-gamma-Glutamylglutamine,1TMS,#1	2579.3982	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TMS,#2	2551.6697	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TMS,#3	2634.3872	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TMS,#4	2656.2603	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TMS,#5	2595.0503	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#1	2558.4048	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#2	2638.3208	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#3	2640.23	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#4	2588.6843	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#5	2629.0134	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#6	2620.4443	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#7	2557.4868	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#8	2706.923	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#9	2778.2427	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#10	2640.9536	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#11	2768.6777	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TMS,#12	2641.8367	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TBDMS,#1	2838.7751	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TBDMS,#2	2822.7983	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TBDMS,#3	2890.5703	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TBDMS,#4	2924.0125	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,1TBDMS,#5	2857.997	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#1	3043.546	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#2	3114.1582	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#3	3113.8071	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#4	3065.859	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#5	3109.7434	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#6	3105.0508	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#7	3050.3472	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#8	3201.745	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#9	3239.7375	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#10	3112.719	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#11	3231.188	https://arxiv.org/abs/1905.12712
N2-gamma-Glutamylglutamine,2TBDMS,#12	3131.941	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9560000000-a956f772592da08ac91b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9314100000-7288034a17d80463b7ca	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0002-0900000000-aa0c06e268e954c25179	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-4910000000-600a5db0fe0b0ab51aa0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-f58241fb59526b57df2d	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a59-0290000000-53ebbfe26a1610c7d206	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-1790000000-8b9c77dbe3ee9bfa3360	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9600000000-7cf2074b159a06a79e69	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0090000000-1e9b60fa2e6418acc332	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bvm-3590000000-ebbac377891f30e322da	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-3685d99d954b21693f1c	2017-09-01	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Placenta
Prostate

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.46 +/- 0.47 uM	Adult (>18 years old)	Both	Normal	7595563	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	117.00 (20.00-214.00) uM	Adult (>18 years old)	Both	Hyperammonemia	2093471	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.07 +/- 0.52 uM	Adult (>18 years old)	Both	Schizophrenia	7595563	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	258.00 uM	Adult (>18 years old)	Both	Hyperammonemia	2093471	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details

Associated Disorders and Diseases

Disease References

Hyperammonemia
Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. [PubMed:2093471 ]
Schizophrenia
Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
Crohn's disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

181500 (Schizophrenia)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028416

KNApSAcK ID

Not Available

Chemspider ID

133013

KEGG Compound ID

C05283

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

150914

PDB ID

Not Available

ChEBI ID

73707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]

Showing metabocard for N2-gamma-Glutamylglutamine (HMDB0011738)

MOL for HMDB0011738 (N2-gamma-Glutamylglutamine)

3D MOL for HMDB0011738 (N2-gamma-Glutamylglutamine)

3D SDF for HMDB0011738 (N2-gamma-Glutamylglutamine)

3D-SDF for HMDB0011738 (N2-gamma-Glutamylglutamine)

PDB for HMDB0011738 (N2-gamma-Glutamylglutamine)

3D PDB for HMDB0011738 (N2-gamma-Glutamylglutamine)

SMILES for HMDB0011738 (N2-gamma-Glutamylglutamine)

INCHI for HMDB0011738 (N2-gamma-Glutamylglutamine)

Structure for HMDB0011738 (N2-gamma-Glutamylglutamine)

3D Structure for HMDB0011738 (N2-gamma-Glutamylglutamine)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS