MiMeDB: Showing metabocard for gamma-Glutamylhistidine (MMDBc0000475)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:36 UTC

Update Date

2024-04-30 19:32:33 UTC

Metabolite ID

MMDBc0000475

Metabolite Identification

Common Name

gamma-Glutamylhistidine

Description

gamma-Glutamylhistidine is a dipeptide composed of gamma-glutamate and histidine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylhistidine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling 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

HMDB0029151
     RDKit          3D
gamma-Glutamylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.8241   -0.7117   -0.5322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8794   -0.0735    0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4945   -0.6228    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4496    0.4856    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203   -0.0829    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.3880    1.4142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.0897   -0.3439 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -1.6840   -0.2011 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7335   -0.9019   -0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    0.5313   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514    0.9270    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9775    2.3093    0.2304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197    2.6969   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    1.5500   -1.1893 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -1.8627    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682   -1.1516    1.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -2.9961    1.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    1.3602    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.9021    1.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911    2.1711   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.3698   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.7190   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886   -0.5423    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.3945    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4049   -1.0516   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220    1.2575    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602    0.9656   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2136   -1.4735   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.7030   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6788   -1.4573   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.9560   -2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    0.3914    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    2.9557    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    3.6799   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -3.8714    1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    3.1438   -0.5583 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 14 10  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 20 36  1  0
M  END


  Mrv1652304062014282D          

 20 20  0  0  0  0            999 V2000
 2497.0108 2499.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.7252 2498.8992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2497.7252 2498.0742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4397 2497.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1542 2498.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.8687 2497.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5832 2498.0742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.2977 2497.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.0121 2498.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.2977 2496.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5832 2498.8992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4397 2496.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4397 2499.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1542 2498.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4397 2500.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.6243 2499.3931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2494.9573 2498.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.2121 2498.1243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0366 2498.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.2913 2498.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 19 20  2  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000475

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O5/c12-7(10(17)18)1-2-9(16)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t7-,8-/m0/s1

> <INCHI_KEY>
PXVCMZCJAUJLJP-YUMQZZPRSA-N

> <FORMULA>
C11H16N4O5

> <MOLECULAR_WEIGHT>
284.272

> <EXACT_MASS>
284.112069631

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.395873732937652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-3.00

> <JCHEM_LOGP>
-6.52015831301296

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.5952982122712127

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6672222021466663

> <JCHEM_PKA_STRONGEST_BASIC>
9.312725670066634

> <JCHEM_POLAR_SURFACE_AREA>
158.4

> <JCHEM_REFRACTIVITY>
65.58109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029151
     RDKit          3D
gamma-Glutamylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.8241   -0.7117   -0.5322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8794   -0.0735    0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4945   -0.6228    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4496    0.4856    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203   -0.0829    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.3880    1.4142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.0897   -0.3439 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -1.6840   -0.2011 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7335   -0.9019   -0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    0.5313   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514    0.9270    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9775    2.3093    0.2304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197    2.6969   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    1.5500   -1.1893 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -1.8627    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682   -1.1516    1.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -2.9961    1.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    1.3602    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.9021    1.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911    2.1711   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.3698   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.7190   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886   -0.5423    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.3945    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4049   -1.0516   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220    1.2575    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602    0.9656   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2136   -1.4735   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.7030   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6788   -1.4573   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.9560   -2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    0.3914    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    2.9557    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    3.6799   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -3.8714    1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    3.1438   -0.5583 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 14 10  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4661.0874665.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4662.4204664.612   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4662.4204663.072   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4663.7544662.300   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4665.0884663.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4666.4224662.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4667.7554663.072   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4669.0894662.300   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4670.4234663.072   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4669.0894660.760   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    4667.7554664.612   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    4663.7544660.760   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    4663.7544665.380   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4665.0884664.612   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4663.7544666.920   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0    4658.4994665.534   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    4657.2544664.629   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    4657.7294663.165   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    4659.2684663.165   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4659.7444664.629   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    4                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   17   20                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   20   18                                                       
CONECT   20   19   16    1                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0029151
HETATM    1  N1  UNL     1      -4.824  -0.712  -0.532  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.879  -0.074   0.356  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.494  -0.623   0.119  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.450   0.486   0.275  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.120  -0.083   0.497  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.599   0.388   1.414  1.00  0.00           O  
HETATM    7  N2  UNL     1       0.405  -1.090  -0.344  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.717  -1.684  -0.201  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.733  -0.902  -0.985  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.986   0.531  -0.665  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.951   0.927   0.253  1.00  0.00           C  
HETATM   12  N3  UNL     1       3.977   2.309   0.230  1.00  0.00           N  
HETATM   13  C9  UNL     1       3.020   2.697  -0.715  1.00  0.00           C  
HETATM   14  N4  UNL     1       2.551   1.550  -1.189  1.00  0.00           N  
HETATM   15  C10 UNL     1       2.126  -1.863   1.215  1.00  0.00           C  
HETATM   16  O2  UNL     1       2.868  -1.152   1.864  1.00  0.00           O  
HETATM   17  O3  UNL     1       1.594  -2.996   1.871  1.00  0.00           O  
HETATM   18  C11 UNL     1      -3.923   1.360   0.485  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.901   1.902   1.628  1.00  0.00           O  
HETATM   20  O5  UNL     1      -3.991   2.171  -0.649  1.00  0.00           O  
HETATM   21  H1  UNL     1      -4.610  -0.370  -1.539  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.679  -1.719  -0.533  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.189  -0.542   1.381  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.184  -1.395   0.873  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.405  -1.052  -0.871  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.722   1.257   0.957  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.360   0.966  -0.790  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.214  -1.473  -1.137  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.710  -2.703  -0.642  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.679  -1.457  -0.975  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.357  -0.956  -2.058  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.731   0.391   0.751  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.510   2.956   0.825  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.862   3.680  -1.062  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.725  -3.871   1.415  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.156   3.144  -0.558  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   18   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6    6    7
CONECT    7    8   28
CONECT    8    9   15   29
CONECT    9   10   30   31
CONECT   10   11   11   14
CONECT   11   12   32
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   15   16   16   17
CONECT   17   35
CONECT   18   19   19   20
CONECT   20   36
END

HMDB0029151
     RDKit          3D
gamma-Glutamylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.8241   -0.7117   -0.5322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8794   -0.0735    0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4945   -0.6228    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4496    0.4856    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203   -0.0829    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.3880    1.4142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.0897   -0.3439 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -1.6840   -0.2011 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7335   -0.9019   -0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    0.5313   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514    0.9270    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9775    2.3093    0.2304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197    2.6969   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    1.5500   -1.1893 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -1.8627    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682   -1.1516    1.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -2.9961    1.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    1.3602    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.9021    1.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911    2.1711   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.3698   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.7190   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886   -0.5423    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.3945    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4049   -1.0516   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220    1.2575    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602    0.9656   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2136   -1.4735   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.7030   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6788   -1.4573   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.9560   -2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    0.3914    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    2.9557    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    3.6799   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -3.8714    1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    3.1438   -0.5583 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 14 10  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 20 36  1  0
M  END

Synonyms

Value	Source
L-gamma-Glu-L-his	ChEBI
L-g-Glu-L-his	Generator
L-Γ-glu-L-his	Generator
g-Glutamylhistidine	Generator
Γ-glutamylhistidine	Generator
gamma-Glutamate histidine dipeptide	HMDB
gamma-Glutamate-histidine dipeptide	HMDB
GE-H dipeptide	HMDB
GEH dipeptide	HMDB
GGlu-his	HMDB
L-gamma-Glutamyl-L-histidine	HMDB
Γ-glu-his	HMDB
Γ-L-glu-L-his	HMDB
Γ-L-glutamyl-L-histidine	HMDB
L-Γ-glutamyl-L-histidine	HMDB
N-Γ-glutamylhistidine	HMDB
N-L-Γ-glutamylhistidine	HMDB
N-L-Γ-glutamyl-L-histidine	HMDB
gamma-Glu-his	HMDB
gamma-L-Glu-L-his	HMDB
gamma-L-Glutamyl-L-histidine	HMDB
N-gamma-Glutamylhistidine	HMDB
N-L-gamma-Glutamylhistidine	HMDB
N-L-gamma-Glutamyl-L-histidine	HMDB
N-Γ-L-glutamyl-L-histidine	HMDB
N-gamma-L-Glutamyl-L-histidine	HMDB
g-Glu-his	HMDB
gamma-Glutamylhistidine	HMDB, ChEBI

Molecular Formula

C₁₁H₁₆N₄O₅

Average Mass

284.272

Monoisotopic Mass

284.112069631

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H16N4O5/c12-7(10(17)18)1-2-9(16)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t7-,8-/m0/s1

InChI Key

PXVCMZCJAUJLJP-YUMQZZPRSA-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
Histidine or derivatives
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Heteroaromatic compound
Azole
Imidazole
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Primary amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Primary aliphatic amine
Carbonyl group
Amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.75 g/L	ALOGPS
logP	-3	ALOGPS
logP	-6.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.67	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.4 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	65.58 m³·mol⁻¹	ChemAxon
Polarizability	27.4 Å³	ChemAxon
Number of Rings	1	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	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0290000000-4de323ab2e1096742dbd	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abl-3970000000-a05caaf5355165c7cca5	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9600000000-0fd89c1449f579232cda	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-f7dd217614bfc3b5cff3	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gc9-2690000000-284a7440eed0f2392685	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fl3-9600000000-feb15479f9df725d813b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-83b4b156bb7913c45ce6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-1900000000-a019559a1eb317d04969	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06si-9300000000-f1e0fcf6ec70a9053ebb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fsi-0590000000-0020288f715d0a7a3cfc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zn9-4930000000-ddad6531dda4c9199f0b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-9700000000-f5e3d9b6ddb2f81091bc	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

Feces
Placenta

Tissue Locations

Placenta

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human mucosa; Human stool; Human supragingival plaque; Human feces; Human saliva; Human subgingival plaque	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	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	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
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0029151

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112147

KNApSAcK ID

Not Available

Chemspider ID

5380197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7017195

PDB ID

Not Available

ChEBI ID

133032

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 gamma-Glutamylhistidine (MMDBc0000475)

MOL for #<Metabolite:0x00007fd1000244e0>

3D MOL for #<Metabolite:0x00007fd1000244e0>

3D SDF for #<Metabolite:0x00007fd1000244e0>

3D-SDF for #<Metabolite:0x00007fd1000244e0>

PDB for #<Metabolite:0x00007fd1000244e0>

3D PDB for #<Metabolite:0x00007fd1000244e0>

SMILES for #<Metabolite:0x00007fd1000244e0>

INCHI for #<Metabolite:0x00007fd1000244e0>

Structure for #<Metabolite:0x00007fd1000244e0>

3D Structure for #<Metabolite:0x00007fd1000244e0>