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Showing metabocard for Glycylleucine (HMDB0000759)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:09 UTC
HMDB IDHMDB0000759
Secondary Accession Numbers
  • HMDB00759
Metabolite Identification
Common NameGlycylleucine
DescriptionGlycylleucine, also known as GL or leucylglycine, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Glycylleucine has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make glycylleucine a potential biomarker for the consumption of these foods. Glycylleucine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Glycylleucine.
Structure
Data?1676999709
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000759 (Glycylleucine)


  Mrv1652305271900142D          

 13 12  0  0  0  0            999 V2000
 2498.5185 2498.1074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.5185 2498.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2499.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9467 2498.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6607 2499.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2500.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8046 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0905 2498.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.3765 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0905 2498.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9467 2498.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2496.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  7  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000759 (Glycylleucine)

HMDB0000759
     RDKit          3D
Glycylleucine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.0409   -1.7361    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2808   -0.5752   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    0.6714    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -0.6019    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    0.4095   -0.2391 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4293    0.1902    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -0.0175   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3651   -0.0109   -1.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -0.2392    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -0.4192   -1.0741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783    1.7725    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    2.1622    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    2.6966   -0.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -2.6451   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029   -1.8921    1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -1.4666    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -0.6836   -1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673    1.3384   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    1.1927    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128    0.3711    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5441    1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464   -1.6266    0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1737    0.3721   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    0.1994    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    0.6458    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9080   -1.0930    0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4624   -1.1857   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897   -0.6478   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    3.3627   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END
Download

3D SDF for HMDB0000759 (Glycylleucine)


  Mrv1652305271900142D          

 13 12  0  0  0  0            999 V2000
 2498.5185 2498.1074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.5185 2498.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2499.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9467 2498.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6607 2499.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2500.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8046 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0905 2498.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.3765 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0905 2498.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2497.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9467 2498.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2326 2496.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  7  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000759

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1

> <INCHI_KEY>
DKEXFJVMVGETOO-LURJTMIESA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.2242

> <EXACT_MASS>
188.116092388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.398615174950535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(2-aminoacetamido)-4-methylpentanoic acid

> <ALOGPS_LOGP>
-2.08

> <JCHEM_LOGP>
-2.6937570967300966

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.950194400372812

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.893318016063013

> <JCHEM_PKA_STRONGEST_BASIC>
8.139582890263707

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
46.9744

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycyl-L-leucine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000759 (Glycylleucine)

HMDB0000759
     RDKit          3D
Glycylleucine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.0409   -1.7361    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2808   -0.5752   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    0.6714    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -0.6019    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    0.4095   -0.2391 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4293    0.1902    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -0.0175   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3651   -0.0109   -1.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -0.2392    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -0.4192   -1.0741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783    1.7725    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    2.1622    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    2.6966   -0.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -2.6451   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029   -1.8921    1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -1.4666    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -0.6836   -1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673    1.3384   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    1.1927    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128    0.3711    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5441    1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464   -1.6266    0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1737    0.3721   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    0.1994    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    0.6458    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9080   -1.0930    0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4624   -1.1857   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897   -0.6478   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    3.3627   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END
Download

PDB for HMDB0000759 (Glycylleucine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    4663.9014663.134   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4663.9014664.673   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4665.2344665.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.5674664.673   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    4667.9004665.440   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0    4665.2344666.980   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    4662.5694662.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4661.2364663.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4659.9034662.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4661.2364664.673   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4665.2344662.362   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4666.5674663.134   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4665.2344660.823   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0000759 (Glycylleucine)

COMPND    HMDB0000759
HETATM    1  C1  UNL     1      -3.041  -1.736   0.538  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.281  -0.575  -0.139  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.042   0.671   0.277  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.856  -0.602   0.318  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.074   0.409  -0.239  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.429   0.190   0.345  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.550  -0.017  -0.496  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.365  -0.011  -1.752  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.909  -0.239   0.002  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.841  -0.419  -1.074  1.00  0.00           N  
HETATM   11  C8  UNL     1      -0.278   1.772   0.195  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.074   2.162   1.347  1.00  0.00           O  
HETATM   13  O3  UNL     1      -0.977   2.697  -0.565  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.994  -2.645  -0.095  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.603  -1.892   1.534  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.108  -1.467   0.681  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.385  -0.684  -1.226  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.267   1.338  -0.586  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.488   1.193   1.076  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.013   0.371   0.768  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.897  -0.544   1.442  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.446  -1.627   0.080  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.174   0.372  -1.340  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.495   0.199   1.362  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.233   0.646   0.590  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.908  -1.093   0.710  1.00  0.00           H  
HETATM   27  H14 UNL     1       4.462  -1.186  -1.684  1.00  0.00           H  
HETATM   28  H15 UNL     1       5.790  -0.648  -0.753  1.00  0.00           H  
HETATM   29  H16 UNL     1      -1.628   3.363  -0.168  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19   20
CONECT    4    5   21   22
CONECT    5    6   11   23
CONECT    6    7   24
CONECT    7    8    8    9
CONECT    9   10   25   26
CONECT   10   27   28
CONECT   11   12   12   13
CONECT   13   29
END
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SMILES for HMDB0000759 (Glycylleucine)

CC(C)C[C@H](NC(=O)CN)C(O)=O
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INCHI for HMDB0000759 (Glycylleucine)

InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1
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Synonyms
ValueSource
G-LChEBI
GLChEBI
Gly-L-leuChEBI
Glycyl-L-leucineChEBI
Glycyl-leucineHMDB
N-Glycyl-L-leucineHMDB
LeucylglycineHMDB
Leu-glyHMDB
Glycylleucine, (D)-isomerHMDB
Gly-leuHMDB
g-L DipeptideHMDB
GL DipeptideHMDB
Glycine leucine dipeptideHMDB
Glycine-leucine dipeptideHMDB
N-GlycylleucineHMDB
NSC 83257HMDB
GlycylleucineChEBI
Chemical FormulaC8H16N2O3
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
IUPAC Name(2S)-2-(2-aminoacetamido)-4-methylpentanoic acid
Traditional Nameglycyl-L-leucine
CAS Registry Number869-19-2
SMILES
CC(C)C[C@H](NC(=O)CN)C(O)=O
InChI Identifier
InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1
InChI KeyDKEXFJVMVGETOO-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxide
  • Organic oxygen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available142.074http://allccs.zhulab.cn/database/detail?ID=AllCCS00000032
[M+H]+Not Available149.628http://allccs.zhulab.cn/database/detail?ID=AllCCS00000032
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.2 g/LALOGPS
logP-2.1ALOGPS
logP-2.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.97 m³·mol⁻¹ChemAxon
Polarizability19.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.60831661259
DarkChem[M-H]-141.69731661259
AllCCS[M+H]+144.02932859911
AllCCS[M-H]-141.932859911
DeepCCS[M+H]+142.88730932474
DeepCCS[M-H]-139.05930932474
DeepCCS[M-2H]-176.31330932474
DeepCCS[M+Na]+151.85230932474
AllCCS[M+H]+144.032859911
AllCCS[M+H-H2O]+140.432859911
AllCCS[M+NH4]+147.432859911
AllCCS[M+Na]+148.432859911
AllCCS[M-H]-141.932859911
AllCCS[M+Na-2H]-143.432859911
AllCCS[M+HCOO]-145.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.4 minutes32390414
Predicted by Siyang on May 30, 20229.8892 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.73 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid265.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid856.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid257.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid161.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid59.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid283.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid282.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)535.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid626.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid228.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid923.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid175.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate416.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA379.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water165.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycylleucineCC(C)C[C@H](NC(=O)CN)C(O)=O2521.1Standard polar33892256
GlycylleucineCC(C)C[C@H](NC(=O)CN)C(O)=O1588.1Standard non polar33892256
GlycylleucineCC(C)C[C@H](NC(=O)CN)C(O)=O1687.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycylleucine,1TMS,isomer #1CC(C)C[C@H](NC(=O)CN)C(=O)O[Si](C)(C)C1657.7Semi standard non polar33892256
Glycylleucine,1TMS,isomer #2CC(C)C[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O1724.9Semi standard non polar33892256
Glycylleucine,1TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN)[Si](C)(C)C1663.0Semi standard non polar33892256
Glycylleucine,2TMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1769.7Semi standard non polar33892256
Glycylleucine,2TMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1720.6Standard non polar33892256
Glycylleucine,2TMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O[Si](C)(C)C2264.2Standard polar33892256
Glycylleucine,2TMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN)[Si](C)(C)C1662.6Semi standard non polar33892256
Glycylleucine,2TMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN)[Si](C)(C)C1698.8Standard non polar33892256
Glycylleucine,2TMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN)[Si](C)(C)C2453.7Standard polar33892256
Glycylleucine,2TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1758.9Semi standard non polar33892256
Glycylleucine,2TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1776.0Standard non polar33892256
Glycylleucine,2TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C2242.8Standard polar33892256
Glycylleucine,2TMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1899.6Semi standard non polar33892256
Glycylleucine,2TMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1819.0Standard non polar33892256
Glycylleucine,2TMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O2428.7Standard polar33892256
Glycylleucine,3TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1768.1Semi standard non polar33892256
Glycylleucine,3TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1835.3Standard non polar33892256
Glycylleucine,3TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1978.6Standard polar33892256
Glycylleucine,3TMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1913.9Semi standard non polar33892256
Glycylleucine,3TMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1887.3Standard non polar33892256
Glycylleucine,3TMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2097.0Standard polar33892256
Glycylleucine,3TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1900.9Semi standard non polar33892256
Glycylleucine,3TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1924.1Standard non polar33892256
Glycylleucine,3TMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2145.7Standard polar33892256
Glycylleucine,4TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1949.7Semi standard non polar33892256
Glycylleucine,4TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1978.5Standard non polar33892256
Glycylleucine,4TMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1907.2Standard polar33892256
Glycylleucine,1TBDMS,isomer #1CC(C)C[C@H](NC(=O)CN)C(=O)O[Si](C)(C)C(C)(C)C1910.0Semi standard non polar33892256
Glycylleucine,1TBDMS,isomer #2CC(C)C[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O1956.1Semi standard non polar33892256
Glycylleucine,1TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN)[Si](C)(C)C(C)(C)C1898.5Semi standard non polar33892256
Glycylleucine,2TBDMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2189.7Semi standard non polar33892256
Glycylleucine,2TBDMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2130.7Standard non polar33892256
Glycylleucine,2TBDMS,isomer #1CC(C)C[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2389.4Standard polar33892256
Glycylleucine,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN)[Si](C)(C)C(C)(C)C2122.8Semi standard non polar33892256
Glycylleucine,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN)[Si](C)(C)C(C)(C)C2082.7Standard non polar33892256
Glycylleucine,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN)[Si](C)(C)C(C)(C)C2524.5Standard polar33892256
Glycylleucine,2TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2216.7Semi standard non polar33892256
Glycylleucine,2TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2153.6Standard non polar33892256
Glycylleucine,2TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2392.6Standard polar33892256
Glycylleucine,2TBDMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2323.5Semi standard non polar33892256
Glycylleucine,2TBDMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2176.8Standard non polar33892256
Glycylleucine,2TBDMS,isomer #4CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2505.1Standard polar33892256
Glycylleucine,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2436.9Semi standard non polar33892256
Glycylleucine,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2395.1Standard non polar33892256
Glycylleucine,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2355.5Standard polar33892256
Glycylleucine,3TBDMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2559.4Semi standard non polar33892256
Glycylleucine,3TBDMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2434.0Standard non polar33892256
Glycylleucine,3TBDMS,isomer #2CC(C)C[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2394.7Standard polar33892256
Glycylleucine,3TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2559.2Semi standard non polar33892256
Glycylleucine,3TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2455.2Standard non polar33892256
Glycylleucine,3TBDMS,isomer #3CC(C)C[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2436.6Standard polar33892256
Glycylleucine,4TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2786.3Semi standard non polar33892256
Glycylleucine,4TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2687.4Standard non polar33892256
Glycylleucine,4TBDMS,isomer #1CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2388.5Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Intestine
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified0.918 +/- 1.35 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.00296 +/- 0.0145 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022228
KNApSAcK IDNot Available
Chemspider ID83812
KEGG Compound IDC02155
BioCyc IDCPD-12312
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5727
PubChem Compound92843
PDB IDNot Available
ChEBI ID73514
Food Biomarker OntologyNot Available
VMH IDGLYLEU
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBolster J M; Vaalburg W; Elsinga P H; Woldring M G; Wynberg H Synthesis of carbon-11 labelled glycine and the dipeptides L-phenylalanylglycine and L-leucylglycine. International journal of radiation applications and instrumentation. Part A, Applied radiation and isotopes (1986), 37(9), 985-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581 ]
  2. Smirnov KV, Syrykh GD, Legen'kov VI, Goland-Ruvinova LG, Medkova IL: [Digestive system status after prolonged space flights]. Kosm Biol Aviakosm Med. 1982 Mar-Apr;16(2):19-22. [PubMed:7070032 ]
  3. 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 ]