MiMeDB: Showing metabocard for gamma-Glutamylisoleucine (MMDBc0000445)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:55 UTC

Update Date

2024-04-30 19:32:26 UTC

Metabolite ID

MMDBc0000445

Metabolite Identification

Common Name

gamma-Glutamylisoleucine

Description

gamma-Glutamylisoleucine is a dipeptide composed of gamma-glutamate and isoleucine, 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-Glutamylisoleucine 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. It is found in urine (PMID: 3782411 ).

Structure

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

HMDB0011170
     RDKit          3D
gamma-Glutamylisoleucine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.0935    1.1099   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632    0.4141   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029    0.2639    0.5342 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8898   -0.4298    1.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.4923   -0.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5645   -0.5527    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    0.0108   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.5981   -1.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -0.0889    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419    0.5706   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2761    0.4393    0.8521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5696   -0.9538    1.0736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4075    1.0212    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4137    0.3629   -0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3521    2.3632   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.8671   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -2.8562   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266   -2.1663   -1.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690    1.7918   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0274    0.3832   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7969   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    1.0308    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -0.5800   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    1.3082    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633   -1.5171    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -0.3543    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    0.0279    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    0.0332   -1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -1.0305    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    0.3984    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.1556    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    1.6361   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.0854   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428    0.9280    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5519   -1.1287    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2599   -1.5773    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    2.8841   -0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -2.7075   -2.1990 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 15 37  1  0
 18 38  1  0
M  END


  Mrv1652312091700242D          

 18 17  0  0  0  0            999 V2000
 2498.9283 2499.5885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.9283 2500.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6427 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2500.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0716 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7861 2500.4135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.5005 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2150 2500.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5005 2501.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7861 2499.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6427 2501.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2138 2499.1749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2497.4994 2499.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7849 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2138 2498.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6427 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2499.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6427 2498.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1 12  1  0  0  0  0
  1 16  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  1  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  1  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000445

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h6-7,9H,3-5,12H2,1-2H3,(H,13,14)(H,15,16)(H,17,18)/t6-,7-,9-/m0/s1

> <INCHI_KEY>
SNCKGJWJABDZHI-ZKWXMUAHSA-N

> <FORMULA>
C11H20N2O5

> <MOLECULAR_WEIGHT>
260.29

> <EXACT_MASS>
260.137221752

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.30783600174685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-[(4S)-4-amino-4-carboxybutanamido]-3-methylpentanoic acid

> <ALOGPS_LOGP>
-2.63

> <JCHEM_LOGP>
-2.466264934526746

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.030156441039168

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9733844136026315

> <JCHEM_PKA_STRONGEST_BASIC>
9.312077121032829

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
62.1817

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-[(4S)-4-amino-4-carboxybutanamido]-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011170
     RDKit          3D
gamma-Glutamylisoleucine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.0935    1.1099   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632    0.4141   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029    0.2639    0.5342 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8898   -0.4298    1.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.4923   -0.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5645   -0.5527    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    0.0108   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.5981   -1.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -0.0889    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419    0.5706   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2761    0.4393    0.8521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5696   -0.9538    1.0736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4075    1.0212    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4137    0.3629   -0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3521    2.3632   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.8671   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -2.8562   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266   -2.1663   -1.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690    1.7918   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0274    0.3832   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7969   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    1.0308    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -0.5800   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    1.3082    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633   -1.5171    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -0.3543    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    0.0279    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    0.0332   -1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -1.0305    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    0.3984    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.1556    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    1.6361   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.0854   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428    0.9280    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5519   -1.1287    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2599   -1.5773    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    2.8841   -0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -2.7075   -2.1990 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 15 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 09-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-17         0                                  
HETATM    1  C   UNK     0    4664.6664665.899   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4664.6664667.439   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4666.0004668.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4667.3334667.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4668.6674668.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.0014667.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.3344668.207   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4672.6684667.439   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4671.3344669.747   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4670.0014665.899   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4666.0004669.747   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4663.3324665.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4661.9994665.899   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4660.6654665.126   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4663.3324663.586   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4666.0004665.126   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    4667.3334665.899   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    4666.0004663.586   0.000  0.00  0.00           O+0
CONECT    1    2   12   16                                                  
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   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16    1   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0011170
HETATM    1  C1  UNL     1       4.094   1.110  -1.435  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.163   0.414  -0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.803   0.264   0.534  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.890  -0.430   1.862  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.825  -0.492  -0.338  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.564  -0.553   0.400  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.630   0.011  -0.108  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.688   0.598  -1.222  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.866  -0.089   0.694  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.042   0.571  -0.010  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.276   0.439   0.852  1.00  0.00           C  
HETATM   12  N2  UNL     1      -4.570  -0.954   1.074  1.00  0.00           N  
HETATM   13  C10 UNL     1      -5.408   1.021   0.093  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.414   0.363  -0.263  1.00  0.00           O  
HETATM   15  O3  UNL     1      -5.352   2.363  -0.241  1.00  0.00           O  
HETATM   16  C11 UNL     1       2.271  -1.867  -0.638  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.569  -2.856  -0.242  1.00  0.00           O  
HETATM   18  O5  UNL     1       3.427  -2.166  -1.336  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.969   1.792  -1.530  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.027   0.383  -2.247  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.201   1.797  -1.389  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.773   1.031   0.615  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.640  -0.580  -0.156  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.427   1.308   0.721  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.663  -1.517   1.738  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.894  -0.354   2.319  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.164   0.028   2.558  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.707   0.033  -1.302  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.580  -1.031   1.321  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.670   0.398   1.666  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.092  -1.156   0.866  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.787   1.636  -0.172  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.239   0.085  -0.974  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.143   0.928   1.841  1.00  0.00           H  
HETATM   35  H17 UNL     1      -5.552  -1.129   1.381  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.260  -1.577   0.307  1.00  0.00           H  
HETATM   37  H19 UNL     1      -6.092   2.884  -0.671  1.00  0.00           H  
HETATM   38  H20 UNL     1       3.426  -2.708  -2.199  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    5   24
CONECT    4   25   26   27
CONECT    5    6   16   28
CONECT    6    7   29
CONECT    7    8    8    9
CONECT    9   10   30   31
CONECT   10   11   32   33
CONECT   11   12   13   34
CONECT   12   35   36
CONECT   13   14   14   15
CONECT   15   37
CONECT   16   17   17   18
CONECT   18   38
END

HMDB0011170
     RDKit          3D
gamma-Glutamylisoleucine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.0935    1.1099   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632    0.4141   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029    0.2639    0.5342 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8898   -0.4298    1.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.4923   -0.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5645   -0.5527    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    0.0108   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.5981   -1.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -0.0889    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419    0.5706   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2761    0.4393    0.8521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5696   -0.9538    1.0736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4075    1.0212    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4137    0.3629   -0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3521    2.3632   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.8671   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -2.8562   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266   -2.1663   -1.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690    1.7918   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0274    0.3832   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7969   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    1.0308    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -0.5800   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    1.3082    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633   -1.5171    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -0.3543    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    0.0279    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    0.0332   -1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -1.0305    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    0.3984    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.1556    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    1.6361   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.0854   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428    0.9280    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5519   -1.1287    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2599   -1.5773    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    2.8841   -0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -2.7075   -2.1990 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 15 37  1  0
 18 38  1  0
M  END

Synonyms

Value	Source
L-gamma-Glu-L-ile	ChEBI
L-g-Glu-L-ile	Generator
L-Γ-glu-L-ile	Generator
g-Glutamylisoleucine	Generator
Γ-glutamylisoleucine	Generator
Γ-glu-ile	HMDB
Γ-L-glu-L-ile	HMDB
Γ-L-glutamyl-L-isoleucine	HMDB
L-Γ-glutamyl-L-isoleucine	HMDB
N-Γ-glutamylisoleucine	HMDB
N-L-Γ-glutamylisoleucine	HMDB
N-L-Γ-glutamyl-L-isoleucine	HMDB
gamma-Glu-ile	HMDB
gamma-L-Glu-L-ile	HMDB
gamma-L-Glutamyl-L-isoleucine	HMDB
L-gamma-Glutamyl-L-isoleucine	HMDB
N-gamma-Glutamylisoleucine	HMDB
N-L-gamma-Glutamylisoleucine	HMDB
N-L-gamma-Glutamyl-L-isoleucine	HMDB
g-Glu-ile	HMDB
N-Γ-L-glutamyl-L-isoleucine	HMDB
N-gamma-L-Glutamyl-L-isoleucine	HMDB
gamma-Glutamylisoleucine	HMDB

Molecular Formula

C₁₁H₂₀N₂O₅

Average Mass

260.29

Monoisotopic Mass

260.137221752

IUPAC Name

(2S,3S)-2-[(4S)-4-amino-4-carboxybutanamido]-3-methylpentanoic acid

Traditional Name

(2S,3S)-2-[(4S)-4-amino-4-carboxybutanamido]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H20N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h6-7,9H,3-5,12H2,1-2H3,(H,13,14)(H,15,16)(H,17,18)/t6-,7-,9-/m0/s1

InChI Key

SNCKGJWJABDZHI-ZKWXMUAHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
Isoleucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Methyl-branched fatty acid
Branched fatty acid
N-acyl-amine
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutamyl-L-amino acid (CHEBI:68434 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.55 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.97	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	62.18 m³·mol⁻¹	ChemAxon
Polarizability	26.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-0490000000-9a8493d1209721c96c45	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-4940000000-c8d2557d4ece2b3e1f48	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9400000000-c4806ce4eb33b070ec04	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aor-0190000000-fba2af6da925fa69e695	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ng-2980000000-c4854314104d3f1dc06f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01x0-9500000000-3ebdef8b8d4284510598	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-37e1c45547c2f6b7c83f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4930000000-656c949a22ffdbe66bb2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-91a811eea14294cf8bbf	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0390000000-c75ac26b7fd31c08f923	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-04a27ca349255e4db60b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-ef578d2b25c43747f2b8	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

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

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	Firmicutes	5	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; 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 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

HMDB0011170

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

18897160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22885096

PDB ID

Not Available

ChEBI ID

68434

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. doi: 10.1016/s0378-4347(00)83502-1. [PubMed:3782411 ]
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-Glutamylisoleucine (MMDBc0000445)

MOL for #<Metabolite:0x00007fd0fe07f978>

3D MOL for #<Metabolite:0x00007fd0fe07f978>

3D SDF for #<Metabolite:0x00007fd0fe07f978>

3D-SDF for #<Metabolite:0x00007fd0fe07f978>

PDB for #<Metabolite:0x00007fd0fe07f978>

3D PDB for #<Metabolite:0x00007fd0fe07f978>

SMILES for #<Metabolite:0x00007fd0fe07f978>

INCHI for #<Metabolite:0x00007fd0fe07f978>

Structure for #<Metabolite:0x00007fd0fe07f978>

3D Structure for #<Metabolite:0x00007fd0fe07f978>