Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2016-10-26 16:31:55 UTC

Update Date

2023-02-21 17:30:39 UTC

HMDB ID

HMDB0062176

Secondary Accession Numbers

HMDB62176

Metabolite Identification

Common Name

N-Lactoylleucine

Description

(2S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-4-methylpentanoic acid belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (2S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-4-methylpentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0062176
     RDKit          3D
N-Lactoylleucine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -3.4192    1.4303   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    0.2898    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -0.9826   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.5203   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629   -0.4207    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1476    0.0943    0.0297 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793    0.4444    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799    0.3535    2.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.9507    0.3762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145   -0.1063   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    1.2392    1.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -1.7701   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -2.0372   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9485   -2.7539    0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.4577   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870    1.2300   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.3820    0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    0.2930    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027   -1.4112   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -0.7456   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.7239    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    0.4969   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    1.5884    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.4361    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594    0.1802   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    1.8683   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297    0.2834   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997   -1.0102    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -0.3364   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    2.1757    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -3.5438    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
M  END


  Mrv1652310261618312D          

 14 13  0  0  0  0            999 V2000
    0.5803    1.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.3017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5803   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    0.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802   -0.9357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485   -0.1107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -0.1107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9919    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    1.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -0.9357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  6  1  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  9 12  2  0  0  0  0
 10 13  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062176

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H17NO4/c1-5(2)4-7(9(13)14)10-8(12)6(3)11/h5-7,11H,4H2,1-3H3,(H,10,12)(H,13,14)/t6-,7-/m0/s1

> <INCHI_KEY>
BUMIGZVUJKNXCO-BQBZGAKWSA-N

> <FORMULA>
C9H17NO4

> <MOLECULAR_WEIGHT>
203.238

> <EXACT_MASS>
203.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.63267153693269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-hydroxypropanamido]-4-methylpentanoic acid

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
0.2457616410000001

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.12449924831764

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.068862450825548

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4633228679993477

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
49.8108

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-hydroxypropanamido]-4-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062176
     RDKit          3D
N-Lactoylleucine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -3.4192    1.4303   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    0.2898    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -0.9826   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.5203   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629   -0.4207    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1476    0.0943    0.0297 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793    0.4444    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799    0.3535    2.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.9507    0.3762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145   -0.1063   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    1.2392    1.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -1.7701   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -2.0372   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9485   -2.7539    0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.4577   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870    1.2300   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.3820    0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    0.2930    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027   -1.4112   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -0.7456   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.7239    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    0.4969   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    1.5884    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.4361    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594    0.1802   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    1.8683   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297    0.2834   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997   -1.0102    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -0.3364   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    2.1757    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -3.5438    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 26-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-OCT-16         0                                  
HETATM    1  C   UNK     0       1.083   2.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.103   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   0.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083  -0.207   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.417   0.563   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.417   2.103   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.083  -1.747   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.584  -0.207   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.918   0.563   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.251  -0.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.585   0.563   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.918   2.103   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.251  -1.747   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.083   4.413   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4                                                            
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    3    9                                                       
CONECT    9   10   12    8                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0062176
HETATM    1  C1  UNL     1      -3.419   1.430  -0.315  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.606   0.290   0.342  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.173  -0.983  -0.266  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.178   0.520  -0.006  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.163  -0.421   0.549  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.148   0.094   0.030  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.179   0.444   0.920  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.080   0.353   2.169  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.464   0.951   0.376  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.015  -0.106  -0.556  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.378   1.239   1.376  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.309  -1.770  -0.017  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.150  -2.037  -1.156  1.00  0.00           O  
HETATM   14  O4  UNL     1      -0.948  -2.754   0.706  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.132   1.458  -1.384  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.487   1.230  -0.216  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.124   2.382   0.140  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.783   0.293   1.432  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.503  -1.411  -1.024  1.00  0.00           H  
HETATM   20  H6  UNL     1      -4.159  -0.746  -0.774  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.380  -1.724   0.528  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.069   0.497  -1.136  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.939   1.588   0.238  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.132  -0.436   1.648  1.00  0.00           H  
HETATM   25  H11 UNL     1       1.259   0.180  -1.001  1.00  0.00           H  
HETATM   26  H12 UNL     1       3.210   1.868  -0.210  1.00  0.00           H  
HETATM   27  H13 UNL     1       4.930   0.283  -1.055  1.00  0.00           H  
HETATM   28  H14 UNL     1       4.200  -1.010   0.052  1.00  0.00           H  
HETATM   29  H15 UNL     1       3.217  -0.336  -1.297  1.00  0.00           H  
HETATM   30  H16 UNL     1       4.703   2.176   1.315  1.00  0.00           H  
HETATM   31  H17 UNL     1      -1.427  -3.544   0.306  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   18
CONECT    3   19   20   21
CONECT    4    5   22   23
CONECT    5    6   12   24
CONECT    6    7   25
CONECT    7    8    8    9
CONECT    9   10   11   26
CONECT   10   27   28   29
CONECT   11   30
CONECT   12   13   13   14
CONECT   14   31
END

HMDB0062176
     RDKit          3D
N-Lactoylleucine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -3.4192    1.4303   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    0.2898    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -0.9826   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.5203   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629   -0.4207    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1476    0.0943    0.0297 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793    0.4444    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799    0.3535    2.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.9507    0.3762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145   -0.1063   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    1.2392    1.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -1.7701   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -2.0372   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9485   -2.7539    0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.4577   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870    1.2300   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.3820    0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    0.2930    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027   -1.4112   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -0.7456   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.7239    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    0.4969   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    1.5884    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.4361    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594    0.1802   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    1.8683   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297    0.2834   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997   -1.0102    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -0.3364   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    2.1757    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -3.5438    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-4-methylpentanoate	Generator
N-Lactoyl-leucine	HMDB

Chemical Formula

C₉H₁₇NO₄

Average Molecular Weight

203.238

Monoisotopic Molecular Weight

203.115758031

IUPAC Name

(2S)-2-[(2S)-2-hydroxypropanamido]-4-methylpentanoic acid

Traditional Name

(2S)-2-[(2S)-2-hydroxypropanamido]-4-methylpentanoic acid

CAS Registry Number

210769-82-7

SMILES

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

InChI Identifier

InChI=1S/C9H17NO4/c1-5(2)4-7(9(13)14)10-8(12)6(3)11/h5-7,11H,4H2,1-3H3,(H,10,12)(H,13,14)/t6-,7-/m0/s1

InChI Key

BUMIGZVUJKNXCO-BQBZGAKWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25964343)

Source

Exogenous

Exogenous (HMDB: HMDB0062176)

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	0.12	ALOGPS
logP	0.25	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.81 m³·mol⁻¹	ChemAxon
Polarizability	20.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	151.559	30932474
DeepCCS	[M-H]-	149.201	30932474
DeepCCS	[M-2H]-	182.197	30932474
DeepCCS	[M+Na]+	157.652	30932474
AllCCS	[M+H]+	147.8	32859911
AllCCS	[M+H-H2O]+	144.2	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	147.1	32859911
AllCCS	[M+HCOO]-	148.6	32859911

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.	2.56 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9029 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1520.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	264.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	101.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	353.4 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	406.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	742.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	341.6 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	1184.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	218.9 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	85.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoylleucine	CC(C)C[C@H](NC(=O)[C@H](C)O)C(O)=O	2924.2	Standard polar	33892256
N-Lactoylleucine	CC(C)C[C@H](NC(=O)[C@H](C)O)C(O)=O	1526.1	Standard non polar	33892256
N-Lactoylleucine	CC(C)C[C@H](NC(=O)[C@H](C)O)C(O)=O	1617.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoylleucine,1TMS,isomer #1	CC(C)C[C@H](NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O	1625.2	Semi standard non polar	33892256
N-Lactoylleucine,1TMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C	1592.1	Semi standard non polar	33892256
N-Lactoylleucine,1TMS,isomer #3	CC(C)C[C@@H](C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C	1607.1	Semi standard non polar	33892256
N-Lactoylleucine,2TMS,isomer #1	CC(C)C[C@H](NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1681.7	Semi standard non polar	33892256
N-Lactoylleucine,2TMS,isomer #2	CC(C)C[C@@H](C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C	1683.1	Semi standard non polar	33892256
N-Lactoylleucine,2TMS,isomer #3	CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C	1643.5	Semi standard non polar	33892256
N-Lactoylleucine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C	1747.3	Semi standard non polar	33892256
N-Lactoylleucine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C	1777.4	Standard non polar	33892256
N-Lactoylleucine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C	1754.3	Standard polar	33892256
N-Lactoylleucine,1TBDMS,isomer #1	CC(C)C[C@H](NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O	1864.4	Semi standard non polar	33892256
N-Lactoylleucine,1TBDMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C(C)(C)C	1824.2	Semi standard non polar	33892256
N-Lactoylleucine,1TBDMS,isomer #3	CC(C)C[C@@H](C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C	1829.7	Semi standard non polar	33892256
N-Lactoylleucine,2TBDMS,isomer #1	CC(C)C[C@H](NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2123.9	Semi standard non polar	33892256
N-Lactoylleucine,2TBDMS,isomer #2	CC(C)C[C@@H](C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2141.6	Semi standard non polar	33892256
N-Lactoylleucine,2TBDMS,isomer #3	CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C	2097.0	Semi standard non polar	33892256
N-Lactoylleucine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2389.2	Semi standard non polar	33892256
N-Lactoylleucine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2360.3	Standard non polar	33892256
N-Lactoylleucine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2208.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylleucine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9200000000-6f0f328b8f5fe1734be4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylleucine GC-MS (2 TMS) - 70eV, Positive	splash10-014i-6921000000-3448e0e9a3efb64a8985	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylleucine 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 - N-Lactoylleucine 10V, Positive-QTOF	splash10-0udr-3950000000-2ab20d6bdc351e10f2cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 20V, Positive-QTOF	splash10-052r-9810000000-02f76c356bb3b6d8e52a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 40V, Positive-QTOF	splash10-0a59-9100000000-4bcffd9115a3e4fce5df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 10V, Negative-QTOF	splash10-0udi-1690000000-6da7aaf4d48b4ef78cdd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 20V, Negative-QTOF	splash10-053r-5910000000-9986e973c6ae6492d7d3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 40V, Negative-QTOF	splash10-00ei-9300000000-7fe8a6f8f14886d4dcd7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 10V, Negative-QTOF	splash10-0f89-0960000000-f36746a7f6db882a5d20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 20V, Negative-QTOF	splash10-001i-1900000000-49ce37b81ad15c1a1624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 40V, Negative-QTOF	splash10-000x-9200000000-6718eb56ee949d47da7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 10V, Positive-QTOF	splash10-0kar-2930000000-28f88c6ee042952dd2b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 20V, Positive-QTOF	splash10-0019-9700000000-bcbe4fa3b6742fca1c9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylleucine 40V, Positive-QTOF	splash10-006y-9000000000-f0ef034000c3d3190ecd	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Adult (>18 years old)	Not Specified	Normal	25964343	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25964343	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

57329455

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

Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]

Showing metabocard for N-Lactoylleucine (HMDB0062176)

MOL for HMDB0062176 (N-Lactoylleucine)

3D MOL for HMDB0062176 (N-Lactoylleucine)

3D SDF for HMDB0062176 (N-Lactoylleucine)

3D-SDF for HMDB0062176 (N-Lactoylleucine)

PDB for HMDB0062176 (N-Lactoylleucine)

3D PDB for HMDB0062176 (N-Lactoylleucine)

SMILES for HMDB0062176 (N-Lactoylleucine)

INCHI for HMDB0062176 (N-Lactoylleucine)

Structure for HMDB0062176 (N-Lactoylleucine)

3D Structure for HMDB0062176 (N-Lactoylleucine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra