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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:11:55 UTC

Update Date

2022-11-23 22:25:18 UTC

HMDB ID

HMDB0253028

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-prolyl-L-leucine

Description

Pro-leu, also known as Z-pro-D-leu or prolylleucine, 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. Pro-leu is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). L-prolyl-l-leucine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically L-prolyl-L-leucine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253028
     RDKit          3D
Pro-leu
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.0657   -1.5432   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.9912    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -1.3902    1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.4950    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    1.1799    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    0.7825    1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9828    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    1.6333   -1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.5711   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.3925   -1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -1.4855   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0450   -0.7186    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219   -0.0853    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793    2.6397    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    3.3668    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    3.2334    1.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.3148   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888   -0.9442   -1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053   -2.5995   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -1.3897    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897   -1.1632    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -0.8292    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -2.4851    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070    0.7459   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    0.9310    0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.9272    2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163    2.1724   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.4503   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -0.8161   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.0528   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -2.2926   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196   -1.8466   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447    0.0520    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -1.4239    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.8812    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021    3.3767    2.0918 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 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  0
  8 27  1  0
  9 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  0
 16 36  1  0
M  END


  Mrv1652310091723182D          

 16 16  0  0  0  0            999 V2000
    3.0301   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7610    2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    1.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8409    1.9435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    0.2211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  4  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253028

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(N=C(O)C1CCCN1)C(O)=O

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

> <INCHI_KEY>
ZKQOUHVVXABNDG-UHFFFAOYSA-N

> <FORMULA>
C11H20N2O3

> <MOLECULAR_WEIGHT>
228.292

> <EXACT_MASS>
228.147392512

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.803185535656795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-1.2123832156762995

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.47824428187096

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4009930857413306

> <JCHEM_PKA_STRONGEST_BASIC>
9.747004520922745

> <JCHEM_POLAR_SURFACE_AREA>
81.92

> <JCHEM_REFRACTIVITY>
59.557

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253028
     RDKit          3D
Pro-leu
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.0657   -1.5432   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.9912    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -1.3902    1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.4950    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    1.1799    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    0.7825    1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9828    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    1.6333   -1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.5711   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.3925   -1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -1.4855   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0450   -0.7186    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219   -0.0853    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793    2.6397    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    3.3668    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    3.2334    1.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.3148   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888   -0.9442   -1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053   -2.5995   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -1.3897    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897   -1.1632    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -0.8292    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -2.4851    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070    0.7459   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    0.9310    0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.9272    2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163    2.1724   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.4503   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -0.8161   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.0528   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -2.2926   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196   -1.8466   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447    0.0520    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -1.4239    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.8812    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021    3.3767    2.0918 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 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  0
  8 27  1  0
  9 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  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0       5.656  -4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.323  -4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.887   5.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.411   3.628   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.427   5.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.990  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.990  -3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.657   2.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.323  -1.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.657   1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.657  -1.897   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.903   3.628   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       8.323   0.413   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      10.991   0.413   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.991  -1.127   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.657  -3.437   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3   12                                                       
CONECT    6    7    9                                                       
CONECT    7    1    2    6                                                  
CONECT    8    4   10   12                                                  
CONECT    9    6   11   13                                                  
CONECT   10    8   13   14                                                  
CONECT   11    9   15   16                                                  
CONECT   12    5    8                                                       
CONECT   13    9   10                                                       
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0253028
HETATM    1  C1  UNL     1      -3.066  -1.543  -0.664  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.112  -0.991   0.374  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.569  -1.390   1.775  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.092   0.495   0.238  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.177   1.180   1.219  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.185   0.782   1.104  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.925   0.983   0.067  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.347   1.633  -1.014  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.326   0.571  -0.044  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.577  -0.393  -1.184  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.451  -1.485  -0.562  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.045  -0.719   0.625  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.822  -0.085   1.144  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.379   2.640   1.071  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.381   3.367   0.867  1.00  0.00           O  
HETATM   16  O3  UNL     1      -2.624   3.233   1.148  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.121  -1.315  -0.370  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.889  -0.944  -1.592  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.905  -2.600  -0.887  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.101  -1.390   0.175  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.790  -1.163   2.506  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.498  -0.829   1.994  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.768  -2.485   1.727  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.807   0.746  -0.804  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.108   0.931   0.387  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.511   0.927   2.260  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.916   2.172  -1.656  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.003   1.450  -0.235  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.634  -0.816  -1.591  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.189   0.053  -1.995  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.833  -2.293  -0.123  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.220  -1.847  -1.249  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.745   0.052   0.252  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.480  -1.424   1.337  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.205  -0.881   1.424  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.002   3.377   2.092  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   14   26
CONECT    6    7    7
CONECT    7    8    9
CONECT    8   27
CONECT    9   10   13   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   35
CONECT   14   15   15   16
CONECT   16   36
END

HMDB0253028
     RDKit          3D
Pro-leu
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.0657   -1.5432   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.9912    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -1.3902    1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.4950    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    1.1799    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    0.7825    1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9828    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    1.6333   -1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.5711   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.3925   -1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -1.4855   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0450   -0.7186    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219   -0.0853    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793    2.6397    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    3.3668    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    3.2334    1.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.3148   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888   -0.9442   -1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053   -2.5995   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -1.3897    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897   -1.1632    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -0.8292    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -2.4851    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070    0.7459   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    0.9310    0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.9272    2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163    2.1724   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.4503   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -0.8161   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.0528   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -2.2926   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196   -1.8466   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447    0.0520    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -1.4239    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.8812    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021    3.3767    2.0918 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 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  0
  8 27  1  0
  9 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  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Z-Pro-D-leu	MeSH
Prolylleucine, (D-leu-D-pro)-isomer	MeSH
Prolylleucine, (L-leu-D-pro)-isomer	MeSH
Prolylleucine, (L-leu-L-pro)-isomer	MeSH
Prolylleucine	MeSH

Chemical Formula

C₁₁H₂₀N₂O₃

Average Molecular Weight

228.292

Monoisotopic Molecular Weight

228.147392512

IUPAC Name

2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid

Traditional Name

2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(N=C(O)C1CCCN1)C(O)=O

InChI Identifier

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

InChI Key

ZKQOUHVVXABNDG-UHFFFAOYSA-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
Proline or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Branched fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Fatty acid
Fatty acyl
Pyrrolidine
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Secondary aliphatic amine
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-0.86	ALOGPS
logP	-1.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.56 m³·mol⁻¹	ChemAxon
Polarizability	24.8 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]+	151.189	30932474
DeepCCS	[M-H]-	147.361	30932474
DeepCCS	[M-2H]-	184.584	30932474
DeepCCS	[M+Na]+	160.248	30932474
AllCCS	[M+H]+	153.1	32859911
AllCCS	[M+H-H2O]+	149.6	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	154.3	32859911
AllCCS	[M+Na-2H]-	154.9	32859911
AllCCS	[M+HCOO]-	155.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pro-leu	CC(C)CC(N=C(O)C1CCCN1)C(O)=O	2430.0	Standard polar	33892256
Pro-leu	CC(C)CC(N=C(O)C1CCCN1)C(O)=O	1849.7	Standard non polar	33892256
Pro-leu	CC(C)CC(N=C(O)C1CCCN1)C(O)=O	1916.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pro-leu,3TMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C)C1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	1941.0	Semi standard non polar	33892256
Pro-leu,3TMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C)C1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	1986.8	Standard non polar	33892256
Pro-leu,3TMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C)C1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2324.1	Standard polar	33892256
Pro-leu,3TBDMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C(C)(C)C)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2603.0	Semi standard non polar	33892256
Pro-leu,3TBDMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C(C)(C)C)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2517.2	Standard non polar	33892256
Pro-leu,3TBDMS,isomer #1	CC(C)CC(N=C(O[Si](C)(C)C(C)(C)C)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2647.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-ea7ffacc9000b013f8e0	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-4-methylpentanoic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	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 - L-prolyl-L-leucine 10V, Positive-QTOF	splash10-01si-4690000000-cf99af9eab8fecc44ceb	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 20V, Positive-QTOF	splash10-0089-9200000000-a02eeb61abff8b3a47e1	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 40V, Positive-QTOF	splash10-05fu-9000000000-c7a3c7faa120fbf9f0da	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 10V, Negative-QTOF	splash10-004i-0290000000-71b955418c80b7943006	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 20V, Negative-QTOF	splash10-003r-5940000000-308fd1a69e54480563ba	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 40V, Negative-QTOF	splash10-008c-9200000000-34fc784032f102db8c69	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 10V, Positive-QTOF	splash10-0059-5890000000-609d0df124b3842b64f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 20V, Positive-QTOF	splash10-0080-9100000000-c0a34388f8d65d81c198	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 40V, Positive-QTOF	splash10-00di-9000000000-c68bc7555080a9d73675	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 10V, Negative-QTOF	splash10-004i-0190000000-ccb1e0bb8452e1a5895a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 20V, Negative-QTOF	splash10-01u0-1900000000-51c5ce34037692bbb91e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-prolyl-L-leucine 40V, Negative-QTOF	splash10-001l-9200000000-6144217e32e925963428	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3527720

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for L-prolyl-L-leucine (HMDB0253028)

MOL for HMDB0253028 (L-prolyl-L-leucine)

3D MOL for HMDB0253028 (L-prolyl-L-leucine)

3D SDF for HMDB0253028 (L-prolyl-L-leucine)

3D-SDF for HMDB0253028 (L-prolyl-L-leucine)

PDB for HMDB0253028 (L-prolyl-L-leucine)

3D PDB for HMDB0253028 (L-prolyl-L-leucine)

SMILES for HMDB0253028 (L-prolyl-L-leucine)

INCHI for HMDB0253028 (L-prolyl-L-leucine)

Structure for HMDB0253028 (L-prolyl-L-leucine)

3D Structure for HMDB0253028 (L-prolyl-L-leucine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra