MiMeDB: Showing metabocard for gamma-Glutamylglutamic acid (MMDBc0000454)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:07 UTC

Update Date

2024-04-30 19:32:27 UTC

Metabolite ID

MMDBc0000454

Metabolite Identification

Common Name

gamma-Glutamylglutamic acid

Description

gamma-Glutamylglutamic acid is a dipeptide composed of gamma-glutamate and glutamic acid. Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serve as metabolic fuel and other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: (1) damage to mitochondria from excessively high intracellular Ca2+ (2) Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produce spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization (Wikipedia).

Structure

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

HMDB0011737
     RDKit          3D
gamma-Glutamylglutamic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
    2.8271   -0.2383    2.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -0.6467    1.0612 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1994    0.5038    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    1.0362   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.0747   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -1.1268   -0.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    0.5006   -0.7917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257   -0.3855   -1.2879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5983   -0.6338   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471    0.6756    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133    0.4619    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.6905    1.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120    1.5581    1.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    0.1071   -2.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    1.1965   -3.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.5432   -3.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.9469    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683   -0.8408    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437   -1.3684    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.1338    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    0.7061    2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -1.5313    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    0.2561   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    1.3252    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    1.5263    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8904    1.8672   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808    1.4785   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.3834   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -1.2832   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.1450    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565    1.3517    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    1.1508   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.4593    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385   -0.1964   -3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305   -1.9257   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 16 34  1  0
 19 35  1  0
M  END

      
  Mrv1652312091700132D          

 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 O   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>
MMDBc0000454

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O7/c11-5(9(16)17)1-3-7(13)12-6(10(18)19)2-4-8(14)15/h5-6H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1

> <INCHI_KEY>
OWQDWQKWSLFFFR-WDSKDSINSA-N

> <FORMULA>
C10H16N2O7

> <MOLECULAR_WEIGHT>
276.2432

> <EXACT_MASS>
276.095750876

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.696033255794767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.19

> <JCHEM_LOGP>
-4.229702790199922

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.4970992953949938

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9275847548165221

> <JCHEM_PKA_STRONGEST_BASIC>
9.31207518878102

> <JCHEM_POLAR_SURFACE_AREA>
167.02

> <JCHEM_REFRACTIVITY>
59.37550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.75e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011737
     RDKit          3D
gamma-Glutamylglutamic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
    2.8271   -0.2383    2.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -0.6467    1.0612 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1994    0.5038    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    1.0362   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.0747   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -1.1268   -0.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    0.5006   -0.7917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257   -0.3855   -1.2879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5983   -0.6338   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471    0.6756    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133    0.4619    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.6905    1.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120    1.5581    1.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    0.1071   -2.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    1.1965   -3.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.5432   -3.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.9469    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683   -0.8408    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437   -1.3684    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.1338    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    0.7061    2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -1.5313    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    0.2561   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    1.3252    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    1.5263    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8904    1.8672   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808    1.4785   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.3834   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -1.2832   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.1450    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565    1.3517    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    1.1508   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.4593    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385   -0.1964   -3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305   -1.9257   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 16 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 09-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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  O   UNK     0    4659.9964667.439   0.000  0.00  0.00           O+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    HMDB0011737
HETATM    1  N1  UNL     1       2.827  -0.238   2.375  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.290  -0.647   1.061  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.199   0.504   0.091  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.823   1.036  -0.089  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.846   0.075  -0.594  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.117  -1.127  -0.869  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.494   0.501  -0.792  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.526  -0.386  -1.288  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.598  -0.634  -0.253  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.247   0.676   0.132  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.313   0.462   1.152  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.541  -0.691   1.552  1.00  0.00           O  
HETATM   13  O3  UNL     1      -5.012   1.558   1.618  1.00  0.00           O  
HETATM   14  C9  UNL     1      -2.123   0.107  -2.541  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.700   1.196  -3.034  1.00  0.00           O  
HETATM   16  O5  UNL     1      -3.119  -0.543  -3.216  1.00  0.00           O  
HETATM   17  C10 UNL     1       4.758  -0.947   1.217  1.00  0.00           C  
HETATM   18  O6  UNL     1       5.368  -0.841   2.286  1.00  0.00           O  
HETATM   19  O7  UNL     1       5.444  -1.368   0.068  1.00  0.00           O  
HETATM   20  H1  UNL     1       1.789  -0.134   2.325  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.209   0.706   2.620  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.725  -1.531   0.774  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.647   0.256  -0.892  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.828   1.325   0.509  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.432   1.526   0.836  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.890   1.867  -0.840  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.781   1.478  -0.584  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.041  -1.383  -1.466  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.405  -1.283  -0.643  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.199  -1.145   0.644  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.457   1.352   0.560  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.634   1.151  -0.792  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.895   1.459   2.100  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.038  -0.196  -3.413  1.00  0.00           H  
HETATM   35  H16 UNL     1       4.930  -1.926  -0.613  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   17   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6    6    7
CONECT    7    8   27
CONECT    8    9   14   28
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   12   13
CONECT   13   33
CONECT   14   15   15   16
CONECT   16   34
CONECT   17   18   18   19
CONECT   19   35
END

HMDB0011737
     RDKit          3D
gamma-Glutamylglutamic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
    2.8271   -0.2383    2.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -0.6467    1.0612 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1994    0.5038    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    1.0362   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.0747   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -1.1268   -0.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    0.5006   -0.7917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257   -0.3855   -1.2879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5983   -0.6338   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471    0.6756    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133    0.4619    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.6905    1.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120    1.5581    1.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    0.1071   -2.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    1.1965   -3.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.5432   -3.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.9469    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683   -0.8408    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437   -1.3684    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.1338    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    0.7061    2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -1.5313    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    0.2561   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    1.3252    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    1.5263    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8904    1.8672   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808    1.4785   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.3834   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -1.2832   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.1450    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565    1.3517    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    1.1508   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.4593    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385   -0.1964   -3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305   -1.9257   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 16 34  1  0
 19 35  1  0
M  END

Synonyms

Value	Source
(5-L-Glutamyl)-L-glutamate	ChEBI
gamma-Glutamylglutamate	ChEBI
gamma-L-Glu-L-glu	ChEBI
(5-L-Glutamyl)-L-glutamic acid	Generator
g-Glutamylglutamate	Generator
g-Glutamylglutamic acid	Generator
Γ-glutamylglutamate	Generator
Γ-glutamylglutamic acid	Generator
g-L-Glu-L-glu	Generator
Γ-L-glu-L-glu	Generator
γ-Glu-Glu	HMDB, Generator
γ-L-Glutamyl-L-glutamic acid	HMDB
γ-L-Glutamyl-L-glutamate	HMDB
L-γ-Glutamyl-L-glutamic acid	HMDB
L-γ-Glutamyl-L-glutamate	HMDB
N-γ-Glutamylglutamic acid	HMDB
N-γ-Glutamylglutamate	HMDB
N-L-γ-Glutamylglutamic acid	HMDB
N-L-γ-Glutamylglutamate	HMDB
N-L-γ-Glutamyl-L-glutamic acid	HMDB
N-L-γ-Glutamyl-L-glutamate	HMDB
gamma-Glu-Glu	HMDB
gamma-L-Glutamyl-L-glutamic acid	HMDB
gamma-L-Glutamyl-L-glutamate	HMDB, MeSH
L-gamma-Glutamyl-L-glutamic acid	HMDB
L-gamma-Glutamyl-L-glutamate	HMDB
N-gamma-Glutamylglutamic acid	HMDB
N-gamma-Glutamylglutamate	HMDB
N-L-gamma-Glutamylglutamic acid	HMDB
N-L-gamma-Glutamylglutamate	HMDB
N-L-gamma-Glutamyl-L-glutamic acid	HMDB
N-L-gamma-Glutamyl-L-glutamate	HMDB
gamma-Glutamylglutamic acid	HMDB, Generator
N-gamma-L-Glutamyl-L-glutamic acid	HMDB
N-γ-L-Glutamyl-L-glutamic acid	HMDB
N-γ-L-Glutamyl-L-glutamate	HMDB
N-gamma-L-Glutamyl-L-glutamate	HMDB
g-Glu-Glu	Generator, HMDB

Molecular Formula

C₁₀H₁₆N₂O₇

Average Mass

276.2432

Monoisotopic Mass

276.095750876

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H16N2O7/c11-5(9(16)17)1-3-7(13)12-6(10(18)19)2-4-8(14)15/h5-6H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1

InChI Key

OWQDWQKWSLFFFR-WDSKDSINSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Primary amine
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73705 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.75 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-4.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	167.02 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	59.38 m³·mol⁻¹	ChemAxon
Polarizability	25.7 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

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	2	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	5	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	24801555
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0011737

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028415

KNApSAcK ID

Not Available

Chemspider ID

83831

KEGG Compound ID

C05282

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92865

PDB ID

Not Available

ChEBI ID

73705

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zheng Y, Yu B, Alexander D, Steffen LM, Boerwinkle E: Human metabolome associates with dietary intake habits among African Americans in the atherosclerosis risk in communities study. Am J Epidemiol. 2014 Jun 15;179(12):1424-33. doi: 10.1093/aje/kwu073. Epub 2014 May 6. [PubMed:24801555 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Showing metabocard for gamma-Glutamylglutamic acid (MMDBc0000454)

MOL for #<Metabolite:0x00007f91f8025620>

3D MOL for #<Metabolite:0x00007f91f8025620>

3D SDF for #<Metabolite:0x00007f91f8025620>

3D-SDF for #<Metabolite:0x00007f91f8025620>

PDB for #<Metabolite:0x00007f91f8025620>

3D PDB for #<Metabolite:0x00007f91f8025620>

SMILES for #<Metabolite:0x00007f91f8025620>

INCHI for #<Metabolite:0x00007f91f8025620>

Structure for #<Metabolite:0x00007f91f8025620>

3D Structure for #<Metabolite:0x00007f91f8025620>