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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

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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	1.93 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7938 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	248.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1050.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	106.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	283.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	306.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	527.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	643.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	256.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	977.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	150.9 seconds	40023050

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

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

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]
Guo K, Li L: Differential 12C-/13C-isotope dansylation labeling and fast liquid chromatography/mass spectrometry for absolute and relative quantification of the metabolome. Anal Chem. 2009 May 15;81(10):3919-32. doi: 10.1021/ac900166a. [PubMed:19309105 ]
Lacha J, Hubacek JA, Potmesil P, Viklicky O, Malek I, Vitko S: TGF-beta I gene polymorphism in heart transplant recipients--effect on renal function. Ann Transplant. 2001;6(1):39-43. [PubMed:11803605 ]
Hebert EM, Mamone G, Picariello G, Raya RR, Savoy G, Ferranti P, Addeo F: Characterization of the pattern of alphas1- and beta-casein breakdown and release of a bioactive peptide by a cell envelope proteinase from Lactobacillus delbrueckii subsp. lactis CRL 581. Appl Environ Microbiol. 2008 Jun;74(12):3682-9. doi: 10.1128/AEM.00247-08. Epub 2008 Apr 18. [PubMed:18424544 ]
Hebert EM, Raya RR, De Giori GS: Nutritional requirements and nitrogen-dependent regulation of proteinase activity of Lactobacillus helveticus CRL 1062. Appl Environ Microbiol. 2000 Dec;66(12):5316-21. [PubMed:11097908 ]
Liu X, Jin W, Theil EC: Opening protein pores with chaotropes enhances Fe reduction and chelation of Fe from the ferritin biomineral. Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3653-8. Epub 2003 Mar 12. [PubMed:12634425 ]
Cole A, Mendelblatt D, Aguayo J, Mathew A, Martin E, Vesely DL: Metastatic prostate cancer (with prostate-specific antigen of 9996) presenting as obstructive jaundice. Am J Med Sci. 2000 Feb;319(2):118-22. [PubMed:10698097 ]
Zhang F, Jia Z, Gao P, Kong H, Li X, Lu X, Wu Y, Xu G: Metabonomics study of urine and plasma in depression and excess fatigue rats by ultra fast liquid chromatography coupled with ion trap-time of flight mass spectrometry. Mol Biosyst. 2010 May;6(5):852-61. doi: 10.1039/b914751a. Epub 2010 Feb 9. [PubMed:20567771 ]
Martichonok V, Plouffe C, Storer AC, Menard R, Jones JB: Aziridine analogs of [[trans-(epoxysuccinyl)-L-leucyl]amino]-4-guanidinobutane (E-64) as inhibitors of cysteine proteases. J Med Chem. 1995 Aug 4;38(16):3078-85. [PubMed:7636871 ]
Guedon E, Renault P, Ehrlich SD, Delorme C: Transcriptional pattern of genes coding for the proteolytic system of Lactococcus lactis and evidence for coordinated regulation of key enzymes by peptide supply. J Bacteriol. 2001 Jun;183(12):3614-22. [PubMed:11371525 ]
Marugg JD, Meijer W, van Kranenburg R, Laverman P, Bruinenberg PG, de Vos WM: Medium-dependent regulation of proteinase gene expression in Lactococcus lactis: control of transcription initiation by specific dipeptides. J Bacteriol. 1995 Jun;177(11):2982-9. [PubMed:7768792 ]
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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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized