MiMeDB: Showing metabocard for epsilon-(gamma-Glutamyl)lysine (MMDBc0000428)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:32 UTC

Update Date

2024-04-30 19:32:23 UTC

Metabolite ID

MMDBc0000428

Metabolite Identification

Common Name

epsilon-(gamma-Glutamyl)lysine

Description

In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688 ). In Parkinson's disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552 ). Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095 ).

Structure

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

HMDB0003869
     RDKit          3D
epsilon-(gamma-Glutamyl)lysine
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.1975   -0.5061    0.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974    0.1777    0.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8578   -0.8967   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.3274   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281    0.5804    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    1.1909    0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1215    0.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.4564    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    1.6502    0.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -0.6074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    0.0147    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -0.9301    0.1717 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3272   -0.0945    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -1.8788   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -2.7269   -1.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -1.8368   -1.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    0.9600   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    0.8177   -1.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.8282   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -0.8345    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9109    0.2336    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    0.7984    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.4651    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1465   -1.6462   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811    0.1873   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -1.1708   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    1.4143    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346    0.0086    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386    1.8358    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.7634   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -0.9033    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.1884    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3043   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878    0.6320   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    0.6739    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -1.5167    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1931    0.8105    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871   -0.6393    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -1.8577   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299    1.9954   -2.5492 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  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
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 16 39  1  0
 19 40  1  0
M  END

  Mrv1652310301922242D          

 19 18  0  0  0  0            999 V2000
10009.820510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.536210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.249710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.965210008.9496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.678710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.394410008.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.678710007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.965210009.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10009.105010008.9496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10008.390910008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.676210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.961110008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.246410008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.531710008.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.816910008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.102110008.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.816910009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.531710007.7121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10009.820510007.7121    0.0000 O   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
  1 19  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  6  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
 11 12  1  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 18  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000428

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

> <INCHI_KEY>
JPKNLFVGUZRHOB-YUMQZZPRSA-N

> <FORMULA>
C11H21N3O5

> <MOLECULAR_WEIGHT>
275.3015

> <EXACT_MASS>
275.148120797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.482068591447984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

> <ALOGPS_LOGP>
-3.96

> <JCHEM_LOGP>
-6.124872556245022

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.5434542312665145

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9415008029820244

> <JCHEM_PKA_STRONGEST_BASIC>
9.733442090281272

> <JCHEM_POLAR_SURFACE_AREA>
155.74

> <JCHEM_REFRACTIVITY>
65.8973

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N(6)-L-gamma-glutamyl-L-lysine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003869
     RDKit          3D
epsilon-(gamma-Glutamyl)lysine
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.1975   -0.5061    0.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974    0.1777    0.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8578   -0.8967   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.3274   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281    0.5804    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    1.1909    0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1215    0.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.4564    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    1.6502    0.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -0.6074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    0.0147    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -0.9301    0.1717 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3272   -0.0945    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -1.8788   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -2.7269   -1.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -1.8368   -1.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    0.9600   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    0.8177   -1.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.8282   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -0.8345    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9109    0.2336    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    0.7984    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.4651    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1465   -1.6462   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811    0.1873   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -1.1708   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    1.4143    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346    0.0086    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386    1.8358    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.7634   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -0.9033    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.1884    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3043   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878    0.6320   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    0.6739    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -1.5167    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1931    0.8105    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871   -0.6393    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -1.8577   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299    1.9954   -2.5492 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  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
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 16 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 30-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-19         0                                  
HETATM    1  C   UNK     0    8684.9988682.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8686.3348683.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8687.6668682.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8689.0028683.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8690.3348682.603   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8691.6698683.373   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8690.3348681.063   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    8689.0028684.912   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    8683.6638683.373   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8682.3308682.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8680.9958683.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8679.6618682.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.3278683.373   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.9928682.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8675.6588683.373   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8674.3248682.603   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8675.6588684.912   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    8676.9928681.063   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0    8684.9988681.063   0.000  0.00  0.00           O+0
CONECT    1    2    9   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0003869
HETATM    1  N1  UNL     1      -6.198  -0.506   0.292  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.897   0.178   0.063  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.858  -0.897  -0.056  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.499  -0.327  -0.289  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.128   0.580   0.846  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.751   1.191   0.681  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.219   0.121   0.627  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.603   0.456   0.470  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.966   1.650   0.382  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.629  -0.607   0.410  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.973   0.015   0.245  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.123  -0.930   0.172  1.00  0.00           C  
HETATM   13  N3  UNL     1       6.327  -0.095   0.013  1.00  0.00           N  
HETATM   14  C10 UNL     1       5.008  -1.879  -0.959  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.092  -2.727  -1.073  1.00  0.00           O  
HETATM   16  O3  UNL     1       5.980  -1.837  -1.976  1.00  0.00           O  
HETATM   17  C11 UNL     1      -4.961   0.960  -1.176  1.00  0.00           C  
HETATM   18  O4  UNL     1      -5.985   0.818  -1.922  1.00  0.00           O  
HETATM   19  O5  UNL     1      -3.989   1.828  -1.570  1.00  0.00           O  
HETATM   20  H1  UNL     1      -6.231  -0.834   1.296  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.911   0.234   0.143  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.753   0.798   0.969  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.826  -1.465   0.915  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.146  -1.646  -0.832  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.481   0.187  -1.266  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.733  -1.171  -0.384  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.847   1.414   0.894  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.135   0.009   1.787  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.539   1.836   1.549  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.719   1.763  -0.279  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.047  -0.903   0.701  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.557  -1.188   1.366  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.374  -1.304  -0.437  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.988   0.632  -0.685  1.00  0.00           H  
HETATM   35  H16 UNL     1       4.141   0.674   1.133  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.161  -1.517   1.103  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.193   0.811   0.530  1.00  0.00           H  
HETATM   38  H19 UNL     1       7.087  -0.639   0.503  1.00  0.00           H  
HETATM   39  H20 UNL     1       6.944  -1.858  -1.635  1.00  0.00           H  
HETATM   40  H21 UNL     1      -3.730   1.995  -2.549  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   27   28
CONECT    6    7   29   30
CONECT    7    8   31
CONECT    8    9    9   10
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   14   36
CONECT   13   37   38
CONECT   14   15   15   16
CONECT   16   39
CONECT   17   18   18   19
CONECT   19   40
END

HMDB0003869
     RDKit          3D
epsilon-(gamma-Glutamyl)lysine
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.1975   -0.5061    0.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974    0.1777    0.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8578   -0.8967   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.3274   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281    0.5804    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    1.1909    0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1215    0.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.4564    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    1.6502    0.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -0.6074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    0.0147    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -0.9301    0.1717 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3272   -0.0945    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -1.8788   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -2.7269   -1.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -1.8368   -1.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    0.9600   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    0.8177   -1.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.8282   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -0.8345    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9109    0.2336    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    0.7984    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.4651    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1465   -1.6462   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811    0.1873   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -1.1708   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    1.4143    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346    0.0086    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386    1.8358    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.7634   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -0.9033    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.1884    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3043   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878    0.6320   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    0.6739    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -1.5167    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1931    0.8105    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871   -0.6393    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -1.8577   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299    1.9954   -2.5492 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  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
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 16 39  1  0
 19 40  1  0
M  END

Synonyms

Value	Source
epsilon-(gamma-L-Glutamyl)-L-lysine	ChEBI
epsilon-(L-gamma-Glutamyl)-L-lysine	ChEBI
gamma-Glu-epsilon-lys	ChEBI
gamma-Glutamyl-epsilon-lysine	ChEBI
L-gamma-Glutamyl-L-epsilon-lysine	ChEBI
N(6)-L-gamma-Glutamyl-L-lysine	ChEBI
N(epsilon)-(gamma-Glutamyl)-lysine	ChEBI
epsilon-(g-L-Glutamyl)-L-lysine	Generator
epsilon-(L-g-Glutamyl)-L-lysine	Generator
g-Glu-epsilon-lys	Generator
g-Glutamyl-epsilon-lysine	Generator
L-g-Glutamyl-L-epsilon-lysine	Generator
N(6)-L-g-Glutamyl-L-lysine	Generator
N(epsilon)-(g-Glutamyl)-lysine	Generator
epsilon-(g-Glutamyl)lysine	Generator
epsilon-(gamma-Glu)-lys	HMDB, MeSH
epsilon-(gamma-Glutamyl)lysine	HMDB
epsilon-(gamma-Glutamyl)lysine isodipeptide	HMDB, MeSH
GGEL peptide	MeSH, HMDB
N-epsilon-(gamma-L-Glutamyl)lysine	MeSH, HMDB
epsilon-(gamma-Glutamyl)-lysine	MeSH, HMDB
Epsilon-(g-Glutamyl)-lysine	Generator, HMDB
N6-L-gamma-Glutamyl-L-lysine	HMDB
N6-L-γ-Glutamyl-L-lysine	HMDB
Nepsilon(gamma-Glutamyl)lysine	HMDB
Nepsilon-(gamma-Glutamyl)-L-lysine	HMDB
Nε(γ-Glutamyl)lysine	HMDB
Nε-(γ-Glutamyl)-L-lysine	HMDB
epsilon-(gamma-L-Glutamyl)lysine	HMDB
epsilonN-(gamma-L-Glutamyl)-L-lysine	HMDB
γ-Glutamyl-ε-lysine	HMDB
ε-(L-γ-Glutamyl)-L-lysine	HMDB
ε-(γ-Glutamyl)lysine	HMDB
ε-(γ-L-Glutamyl)-L-lysine	HMDB
ε-(γ-L-Glutamyl)lysine	HMDB
εN-(γ-L-Glutamyl)-L-lysine	HMDB

Molecular Formula

C₁₁H₂₁N₃O₅

Average Mass

275.3015

Monoisotopic Mass

275.148120797

IUPAC Name

(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

Traditional Name

N(6)-L-gamma-glutamyl-L-lysine

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

InChI Key

JPKNLFVGUZRHOB-YUMQZZPRSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-5940000000-d882bed3b5529ecff7f9	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-6639100000-f6ca1e086349e3426243	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0490000000-072f36ed9a7b3013d059	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2930000000-392395a44df2ae8037f8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9500000000-6e7ed98ff09e19e298dc	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0190000000-58b6ca56f7cccfc512be	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aba-1690000000-fc6b7fb17538a52f8f98	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006w-9700000000-4409c236d141d5814427	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0190000000-87a26493d0e45ab09e99	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1930000000-3595f6a3ff829eac51de	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-8574eb2f5fa536d0c5ab	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0059-0390000000-6d00013244e4fc3d3d9b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9430000000-86b20a12b25ddf059e72	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9200000000-6238074e2599c8441ec5	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for epsilon-(gamma-Glutamyl)lysine (MMDBc0000428)

MOL for #<Metabolite:0x00007fb7e0405a48>

3D MOL for #<Metabolite:0x00007fb7e0405a48>

3D SDF for #<Metabolite:0x00007fb7e0405a48>

3D-SDF for #<Metabolite:0x00007fb7e0405a48>

PDB for #<Metabolite:0x00007fb7e0405a48>

3D PDB for #<Metabolite:0x00007fb7e0405a48>

SMILES for #<Metabolite:0x00007fb7e0405a48>

INCHI for #<Metabolite:0x00007fb7e0405a48>

Structure for #<Metabolite:0x00007fb7e0405a48>

3D Structure for #<Metabolite:0x00007fb7e0405a48>