Showing metabocard for gamma-Glutamylglycine (MMDBc0000453)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:06 UTC
Update Date2024-04-30 19:32:27 UTC
Metabolite IDMMDBc0000453
Metabolite Identification
Common Namegamma-Glutamylglycine
Descriptiongamma-Glutamylglycine is one of the dipeptides that is commonly produced from polypeptides by the action of the enzyme dipeptidyl peptidase. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin. gamma-Glutamylglycine is an excitatory amino acid receptor antagonist with a structure similar to gamma-aminobutyric acid (GABA) (PMID: 6146532 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fb7ec0f85d8>

      
  Mrv1652312081700042D          

 14 13  0  0  0  0            999 V2000
 2500.3574 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7826 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.5023 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2172 2500.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5023 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fb7ec0f85d8>

HMDB0011667
     RDKit          3D
gamma-Glutamylglycine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.6218   -1.5217    0.7166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080   -0.1713    0.1618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3781    0.1755   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    0.1040    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    0.4227    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    0.7098   -1.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235    0.4056    0.9730 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    0.7080    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -0.2589   -0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953   -1.1510   -0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.1741   -1.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751   -0.1095   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391   -1.1257   -1.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0274    1.0791   -1.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887   -1.9182    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -2.1249    0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    0.4930    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -0.5222   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169    1.2049   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003   -0.9728    0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    0.7257    1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    0.1630    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409    0.6661    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    1.7606    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9343   -0.5004   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612    1.9326   -0.9913 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  2  0
  9 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 14 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fb7ec0f85d8>

      
  Mrv1652312081700042D          

 14 13  0  0  0  0            999 V2000
 2500.3574 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7826 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.5023 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2172 2500.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5023 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000453

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1

> <INCHI_KEY>
ACIJGUBIMXQCMF-BYPYZUCNSA-N

> <FORMULA>
C7H12N2O5

> <MOLECULAR_WEIGHT>
204.1806

> <EXACT_MASS>
204.074621504

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.815391233414246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(carboxymethyl)carbamoyl]butanoic acid

> <ALOGPS_LOGP>
-3.47

> <JCHEM_LOGP>
-4.386040058717441

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.777323269397436

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8299819439990146

> <JCHEM_PKA_STRONGEST_BASIC>
9.312086338522867

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
44.0912

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-(carboxymethylcarbamoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fb7ec0f85d8>

HMDB0011667
     RDKit          3D
gamma-Glutamylglycine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.6218   -1.5217    0.7166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080   -0.1713    0.1618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3781    0.1755   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    0.1040    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    0.4227    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    0.7098   -1.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235    0.4056    0.9730 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    0.7080    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -0.2589   -0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953   -1.1510   -0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.1741   -1.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751   -0.1095   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391   -1.1257   -1.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0274    1.0791   -1.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887   -1.9182    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -2.1249    0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    0.4930    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -0.5222   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169    1.2049   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003   -0.9728    0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    0.7257    1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    0.1630    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409    0.6661    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    1.7606    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9343   -0.5004   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612    1.9326   -0.9913 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  2  0
  9 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 14 26  1  0
M  END
Download

PDB for #<Metabolite:0x00007fb7ec0f85d8>

HEADER    PROTEIN                                 08-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-DEC-17         0                                  
HETATM    1  C   UNK     0    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4672.6724667.051   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0    4670.0034668.592   0.000  0.00  0.00           N+0
CONECT    1    2    9                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for #<Metabolite:0x00007fb7ec0f85d8>

COMPND    HMDB0011667
HETATM    1  N1  UNL     1      -2.622  -1.522   0.717  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.708  -0.171   0.162  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.378   0.176  -0.476  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.326   0.104   0.603  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.020   0.423   0.105  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.183   0.710  -1.095  1.00  0.00           O  
HETATM    7  N2  UNL     1       2.124   0.406   0.973  1.00  0.00           N  
HETATM    8  C5  UNL     1       3.477   0.708   0.556  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.872  -0.259  -0.489  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.095  -1.151  -0.878  1.00  0.00           O  
HETATM   11  O3  UNL     1       5.130  -0.174  -1.048  1.00  0.00           O  
HETATM   12  C7  UNL     1      -3.775  -0.110  -0.857  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.439  -1.126  -1.120  1.00  0.00           O  
HETATM   14  O5  UNL     1      -4.027   1.079  -1.510  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.589  -1.918   0.792  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.029  -2.125   0.092  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.970   0.493   0.985  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.149  -0.522  -1.293  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.417   1.205  -0.883  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.300  -0.973   0.941  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.610   0.726   1.467  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.970   0.163   1.975  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.141   0.666   1.440  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.554   1.761   0.189  1.00  0.00           H  
HETATM   25  H11 UNL     1       5.934  -0.500  -0.542  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.161   1.933  -0.991  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   10   11
CONECT   11   25
CONECT   12   13   13   14
CONECT   14   26
END
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SMILES for #<Metabolite:0x00007fb7ec0f85d8>

N[C@@H](CCC(=O)NCC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fb7ec0f85d8>

InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1
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Synonyms
Molecular FormulaC7H12N2O5
Average Mass204.1806
Monoisotopic Mass204.074621504
IUPAC Name(2S)-2-amino-4-[(carboxymethyl)carbamoyl]butanoic acid
Traditional Name(2S)-2-amino-4-(carboxymethylcarbamoyl)butanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1
InChI KeyACIJGUBIMXQCMF-BYPYZUCNSA-N