MiMeDB: Showing metabocard for N2-gamma-Glutamylglutamine (MMDBc0000455)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:09 UTC

Update Date

2024-04-30 19:32:27 UTC

Metabolite ID

MMDBc0000455

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

HMDB0011738
     RDKit          3D
N2-gamma-Glutamylglutamine
 36 35  0  0  0  0  0  0  0  0999 V2000
    2.8400    2.8721    0.7886 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    1.5963    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.4961   -0.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    0.4758    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.8727    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.3803    0.7965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7509   -0.6101    0.6291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -0.9505   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -2.0083   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141   -0.1321   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.7809   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -0.0385   -1.7151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4821    1.3007   -2.1739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398   -0.1066   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    0.9728   -0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.3384    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568   -1.7626    2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -1.3768    3.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.5007    2.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    3.3286    1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    3.3827    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362    0.6856    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678    0.5211    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.8426   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -1.6643    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -2.3833    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    0.2595    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.1360    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.8856   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -1.0042   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796   -1.7842   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -0.6027   -2.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    2.0045   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432    1.5940   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6443   -1.8502   -0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -2.3433    3.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  6
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 16 35  1  0
 19 36  1  0
M  END

      
  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>
MMDBc0000455

> <DATABASE_NAME>
MIME

> <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

$$$$

HMDB0011738
     RDKit          3D
N2-gamma-Glutamylglutamine
 36 35  0  0  0  0  0  0  0  0999 V2000
    2.8400    2.8721    0.7886 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    1.5963    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.4961   -0.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    0.4758    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.8727    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.3803    0.7965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7509   -0.6101    0.6291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -0.9505   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -2.0083   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141   -0.1321   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.7809   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -0.0385   -1.7151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4821    1.3007   -2.1739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398   -0.1066   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    0.9728   -0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.3384    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568   -1.7626    2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -1.3768    3.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.5007    2.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    3.3286    1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    3.3827    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362    0.6856    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678    0.5211    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.8426   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -1.6643    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -2.3833    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    0.2595    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.1360    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.8856   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -1.0042   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796   -1.7842   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -0.6027   -2.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    2.0045   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432    1.5940   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6443   -1.8502   -0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -2.3433    3.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  6
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 16 35  1  0
 19 36  1  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    HMDB0011738
HETATM    1  N1  UNL     1       2.840   2.872   0.789  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.758   1.596   0.167  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.849   1.496  -0.723  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.648   0.476   0.509  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.171  -0.873   0.135  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.940  -1.380   0.796  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.751  -0.610   0.629  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.283  -0.951  -0.277  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.107  -2.008  -0.962  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.514  -0.132  -0.434  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.379  -0.781  -1.466  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.665  -0.038  -1.715  1.00  0.00           C  
HETATM   13  N3  UNL     1      -3.482   1.301  -2.174  1.00  0.00           N  
HETATM   14  C9  UNL     1      -4.540  -0.107  -0.507  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.993   0.973  -0.056  1.00  0.00           O  
HETATM   16  O4  UNL     1      -4.816  -1.338   0.064  1.00  0.00           O  
HETATM   17  C10 UNL     1       2.157  -1.763   2.218  1.00  0.00           C  
HETATM   18  O5  UNL     1       1.303  -1.377   3.056  1.00  0.00           O  
HETATM   19  O6  UNL     1       3.220  -2.501   2.654  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.749   3.329   1.004  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.971   3.383   1.044  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.636   0.686   0.018  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.868   0.521   1.614  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.950  -0.843  -0.975  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.950  -1.664   0.230  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.732  -2.383   0.272  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.594   0.260   1.221  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.020  -0.136   0.554  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.184   0.886  -0.706  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.848  -1.004  -2.398  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.680  -1.784  -1.043  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.206  -0.603  -2.519  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.311   2.005  -1.450  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.143   1.594  -2.914  1.00  0.00           H  
HETATM   35  H16 UNL     1      -5.644  -1.850  -0.171  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.727  -2.343   3.515  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    4
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   17   26
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   14   32
CONECT   13   33   34
CONECT   14   15   15   16
CONECT   16   35
CONECT   17   18   18   19
CONECT   19   36
END

HMDB0011738
     RDKit          3D
N2-gamma-Glutamylglutamine
 36 35  0  0  0  0  0  0  0  0999 V2000
    2.8400    2.8721    0.7886 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    1.5963    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.4961   -0.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    0.4758    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.8727    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.3803    0.7965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7509   -0.6101    0.6291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -0.9505   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -2.0083   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141   -0.1321   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.7809   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -0.0385   -1.7151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4821    1.3007   -2.1739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398   -0.1066   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    0.9728   -0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.3384    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568   -1.7626    2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -1.3768    3.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.5007    2.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    3.3286    1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    3.3827    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362    0.6856    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678    0.5211    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.8426   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -1.6643    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -2.3833    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    0.2595    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.1360    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.8856   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -1.0042   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796   -1.7842   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -0.6027   -2.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    2.0045   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432    1.5940   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6443   -1.8502   -0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -2.3433    3.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  6
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 16 35  1  0
 19 36  1  0
M  END

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, Generator
γ-Glutamylglutamine	HMDB, Generator
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, MeSH
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
N2-gamma-Glutamylglutamine	HMDB
g-Glutamyl glutamine	Generator, HMDB
γ-glutamyl glutamine	Generator, HMDB
g-Glu-Gln	Generator, HMDB
g-Glutamylglutamine	Generator, HMDB

Molecular Formula

C₁₀H₁₇N₃O₆

Average Mass

275.2585

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-003r-1890000000-67e2a8a728d6d9284900	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-7920000000-b10be01edd52864984d9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9400000000-0858c9106ad20fc5ab29	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05i1-0690000000-69500aeda2576335308b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-4930000000-4726b064634cf0a3ba47	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-c59d2d2a2410fa5f7650	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate

Tissue Locations

Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Hyperammonemia	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	2093471
Hyperammonemia		Association	Human Blood	HMDB	2093471
Schizophrenia	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	7595563

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human ; Human urine; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	258				uM	Adult (>18 years old)	Both	Hyperammonemia	HMDB	2093471
Human Blood	Detected and Quantified	117.00		20.00	214.00	uM	Adult (>18 years old)	Both	Hyperammonemia	HMDB	2093471
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.07	0.52			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	7595563
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.46	0.47			uM	Adult (>18 years old)	Both	Normal	HMDB	7595563
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620

External Links

HMDB ID

HMDB0011738

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

References

Synthesis Reference

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 (MMDBc0000455)

MOL for #<Metabolite:0x00007fd12eaa59b8>

3D MOL for #<Metabolite:0x00007fd12eaa59b8>

3D SDF for #<Metabolite:0x00007fd12eaa59b8>

3D-SDF for #<Metabolite:0x00007fd12eaa59b8>

PDB for #<Metabolite:0x00007fd12eaa59b8>

3D PDB for #<Metabolite:0x00007fd12eaa59b8>

SMILES for #<Metabolite:0x00007fd12eaa59b8>

INCHI for #<Metabolite:0x00007fd12eaa59b8>

Structure for #<Metabolite:0x00007fd12eaa59b8>

3D Structure for #<Metabolite:0x00007fd12eaa59b8>