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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-10-29 15:22:04 UTC

Update Date

2021-09-14 15:46:19 UTC

HMDB ID

HMDB0011175

Secondary Accession Numbers

HMDB0028937
HMDB11175
HMDB28937

Metabolite Identification

Common Name

Leucylproline

Description

Leucylproline, also known as L-leu-L-pro or LP, 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. Leucylproline 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 Leucylproline.

Structure

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

HMDB0011175
     RDKit          3D
Leucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.3514    1.3526    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528    0.5641   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1307    0.1457   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -0.6994   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.5525    0.8572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4065   -1.8902    1.1506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786    0.3191    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    1.4974   -0.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.1033   -0.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -1.3824    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -1.3718   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039   -0.1124   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.7539   -0.5804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0811    1.5563    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    1.4643    1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4454    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201    1.9736    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582    0.6148    1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    2.0531    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    1.1998   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473   -0.1762   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    1.0159   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371   -0.7011   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8278   -1.2384   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.3719    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -0.1875    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -1.9377    2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969   -2.6286    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486   -2.2155   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -1.5963    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069   -1.3334    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5322   -2.2414   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -0.3037   -2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093    0.3487   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223    1.4127   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    3.3262    0.6392 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

      
  Mrv1652303081900032D          

 16 16  0  0  0  0            999 V2000
 2500.3943 2500.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2500.8386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9585 2500.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2435 2500.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5227 2500.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2435 2501.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2501.6641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1091 2500.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7625 2499.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4771 2499.0957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7625 2500.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3766 2499.5898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7091 2499.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9641 2498.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7891 2498.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0440 2499.1047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 16  9  1  6  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011175

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O3/c1-7(2)6-8(12)10(14)13-5-3-4-9(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t8-,9-/m0/s1

> <INCHI_KEY>
VTJUNIYRYIAIHF-IUCAKERBSA-N

> <FORMULA>
C11H20N2O3

> <MOLECULAR_WEIGHT>
228.292

> <EXACT_MASS>
228.147392512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.34319228027559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-1.8530815355440537

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.915475102661597

> <JCHEM_PKA_STRONGEST_BASIC>
8.425445457559618

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
59.15740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011175
     RDKit          3D
Leucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.3514    1.3526    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528    0.5641   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1307    0.1457   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -0.6994   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.5525    0.8572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4065   -1.8902    1.1506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786    0.3191    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    1.4974   -0.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.1033   -0.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -1.3824    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -1.3718   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039   -0.1124   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.7539   -0.5804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0811    1.5563    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    1.4643    1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4454    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201    1.9736    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582    0.6148    1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    2.0531    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    1.1998   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473   -0.1762   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    1.0159   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371   -0.7011   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8278   -1.2384   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.3719    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -0.1875    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -1.9377    2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969   -2.6286    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486   -2.2155   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -1.5963    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069   -1.3334    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5322   -2.2414   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -0.3037   -2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093    0.3487   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223    1.4127   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    3.3262    0.6392 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

HEADER    PROTEIN                                 08-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-19         0                                  
HETATM    1  C   UNK     0    4667.4034667.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.0684668.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4664.7234667.487   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4663.3884668.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4662.0424667.506   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.3884669.796   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4666.0684669.773   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4668.7374668.232   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4669.9574665.747   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4671.2914664.979   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4669.9574667.288   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4667.3704665.901   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4666.1244664.995   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4666.6004663.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4668.1404663.531   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.6154664.995   0.000  0.00  0.00           C+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9   10   11   16                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16    1                                                  
CONECT   13   14   12                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12    9                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0011175
HETATM    1  C1  UNL     1       3.351   1.353   0.794  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.853   0.564  -0.398  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.131   0.146  -1.148  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.175  -0.699  -0.018  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.954  -0.552   0.857  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.407  -1.890   1.151  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.079   0.319   0.266  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.268   1.497  -0.004  1.00  0.00           O  
HETATM    9  N2  UNL     1      -1.420  -0.103  -0.007  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.030  -1.382   0.209  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.354  -1.372  -0.481  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.404  -0.112  -1.318  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.439   0.754  -0.580  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.081   1.556   0.487  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.749   1.464   1.693  1.00  0.00           O  
HETATM   16  O3  UNL     1      -4.088   2.445   0.151  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.220   1.974   0.425  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.758   0.615   1.516  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.646   2.053   1.221  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.287   1.200  -1.119  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.847  -0.176  -0.354  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.600   1.016  -1.643  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.937  -0.701  -1.819  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.828  -1.238  -0.936  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.932  -1.372   0.436  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.309  -0.188   1.843  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.051  -1.938   2.123  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.097  -2.629   0.911  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.449  -2.215  -0.280  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.204  -1.596   1.282  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.207  -1.333   0.240  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.532  -2.241  -1.142  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.121  -0.304  -2.369  1.00  0.00           H  
HETATM   34  H18 UNL     1      -4.409   0.349  -1.304  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.922   1.413  -1.322  1.00  0.00           H  
HETATM   36  H20 UNL     1      -4.162   3.326   0.639  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6    7   26
CONECT    6   27   28
CONECT    7    8    8    9
CONECT    9   10   13
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35
CONECT   14   15   15   16
CONECT   16   36
END

HMDB0011175
     RDKit          3D
Leucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.3514    1.3526    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528    0.5641   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1307    0.1457   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -0.6994   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.5525    0.8572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4065   -1.8902    1.1506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786    0.3191    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    1.4974   -0.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.1033   -0.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -1.3824    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -1.3718   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039   -0.1124   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.7539   -0.5804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0811    1.5563    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    1.4643    1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4454    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201    1.9736    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582    0.6148    1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    2.0531    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    1.1998   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473   -0.1762   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    1.0159   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371   -0.7011   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8278   -1.2384   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.3719    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -0.1875    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -1.9377    2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969   -2.6286    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486   -2.2155   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -1.5963    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069   -1.3334    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5322   -2.2414   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -0.3037   -2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093    0.3487   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223    1.4127   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    3.3262    0.6392 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Leu-L-pro	ChEBI
L-P	ChEBI
LP	ChEBI
1-L-Leucyl-L-proline	HMDB
L-Leucyl-L-proline	HMDB
L-p Dipeptide	HMDB
LP Dipeptide	HMDB
Leu-pro	HMDB
Leucine proline dipeptide	HMDB
Leucine-proline dipeptide	HMDB
Leucyl-proline	HMDB
Leucylproline	ChEBI

Chemical Formula

C₁₁H₂₀N₂O₃

Average Molecular Weight

228.292

Monoisotopic Molecular Weight

228.147392512

IUPAC Name

(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

6403-35-6

SMILES

CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H20N2O3/c1-7(2)6-8(12)10(14)13-5-3-4-9(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t8-,9-/m0/s1

InChI Key

VTJUNIYRYIAIHF-IUCAKERBSA-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
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73580 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011175)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 25486321)

Source

Endogenous

Endogenous (HMDB: HMDB0011175)

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	44.6 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-1.9	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	8.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.16 m³·mol⁻¹	ChemAxon
Polarizability	24.34 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.37	30932474
DeepCCS	[M-H]-	157.012	30932474
DeepCCS	[M-2H]-	189.899	30932474
DeepCCS	[M+Na]+	165.463	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leucylproline	CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2737.1	Standard polar	33892256
Leucylproline	CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1875.1	Standard non polar	33892256
Leucylproline	CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1937.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leucylproline,1TMS,isomer #1	CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1898.7	Semi standard non polar	33892256
Leucylproline,1TMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1934.1	Semi standard non polar	33892256
Leucylproline,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1916.0	Semi standard non polar	33892256
Leucylproline,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2003.5	Standard non polar	33892256
Leucylproline,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2455.3	Standard polar	33892256
Leucylproline,2TMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2054.0	Semi standard non polar	33892256
Leucylproline,2TMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2055.0	Standard non polar	33892256
Leucylproline,2TMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2641.0	Standard polar	33892256
Leucylproline,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2096.9	Semi standard non polar	33892256
Leucylproline,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2130.5	Standard non polar	33892256
Leucylproline,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2290.9	Standard polar	33892256
Leucylproline,1TBDMS,isomer #1	CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2128.3	Semi standard non polar	33892256
Leucylproline,1TBDMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2168.6	Semi standard non polar	33892256
Leucylproline,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2400.0	Semi standard non polar	33892256
Leucylproline,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2388.7	Standard non polar	33892256
Leucylproline,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2627.7	Standard polar	33892256
Leucylproline,2TBDMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2509.6	Semi standard non polar	33892256
Leucylproline,2TBDMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2469.7	Standard non polar	33892256
Leucylproline,2TBDMS,isomer #2	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2726.2	Standard polar	33892256
Leucylproline,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2751.8	Semi standard non polar	33892256
Leucylproline,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2695.6	Standard non polar	33892256
Leucylproline,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2606.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leucylproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 10V, Positive-QTOF	splash10-01t9-1290000000-a7d4bfdd98e774a63ec6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 20V, Positive-QTOF	splash10-02ti-9320000000-11c16428d6d853c82e2d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 40V, Positive-QTOF	splash10-066r-9000000000-1f0cc62f9745c1b92db3	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 10V, Negative-QTOF	splash10-0059-0690000000-abfdecce35ead141486f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 20V, Negative-QTOF	splash10-01si-3930000000-da0f5e7072ac2161b71e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 40V, Negative-QTOF	splash10-03mj-9600000000-7be81d5eb7b4a169cabc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 10V, Negative-QTOF	splash10-004i-0290000000-eeda503ca1f26574eff9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 20V, Negative-QTOF	splash10-03di-5920000000-79943170b00abeee82ab	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 40V, Negative-QTOF	splash10-03dj-9400000000-af008c1e3b0451414844	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 10V, Positive-QTOF	splash10-004i-1290000000-a2306aff6fd871be8a62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 20V, Positive-QTOF	splash10-016s-9440000000-8aba88214d533f7870e0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylproline 40V, Positive-QTOF	splash10-00di-9000000000-db271194855430c100f9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Urine	Detected and Quantified	0.03 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	21799048	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027947

KNApSAcK ID

Not Available

Chemspider ID

72971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

80817

PDB ID

Not Available

ChEBI ID

73580

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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Showing metabocard for Leucylproline (HMDB0011175)

MOL for HMDB0011175 (Leucylproline)

3D MOL for HMDB0011175 (Leucylproline)

3D SDF for HMDB0011175 (Leucylproline)

3D-SDF for HMDB0011175 (Leucylproline)

PDB for HMDB0011175 (Leucylproline)

3D PDB for HMDB0011175 (Leucylproline)

SMILES for HMDB0011175 (Leucylproline)

INCHI for HMDB0011175 (Leucylproline)

Structure for HMDB0011175 (Leucylproline)

3D Structure for HMDB0011175 (Leucylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra