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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-03 00:15:09 UTC

Update Date

2022-10-24 19:44:11 UTC

HMDB ID

HMDB0013131

Secondary Accession Numbers

HMDB0061633
HMDB13131
HMDB61633

Metabolite Identification

Common Name

3-Hydroxyhexanoylcarnitine

Description

Hydroxyhexanoycarnitine is an acylcarnitine. More specifically, it is an hydroxyhexanoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Hydroxyhexanoycarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine hydroxyhexanoycarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0013131
     RDKit          3D
3-Hydroxyhexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.0282   -1.0628   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205   -0.8925   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    0.3505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5220    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9329   -0.5689    0.6438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    0.9207   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857    1.0610   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2178    1.3898   -2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    0.8128   -0.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526    0.9373   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7590    2.0212    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.5922    2.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    1.1933    2.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518    1.5903    3.1496 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9715   -0.3979    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -0.6623   -0.0221 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8098   -0.9959   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.9125    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    0.2740    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -0.0627   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583   -1.4399    0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776   -1.7682   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -1.8064   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -0.7724   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2395    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.1777    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    1.3736    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -1.3992    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    0.0935   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7182    1.8837   -1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    1.2373   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    2.8740    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    2.3320    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.5623    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.1773   -0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768   -1.5336   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9878   -0.0858   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854   -1.6191   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.6839    1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -2.5959    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809   -2.2689    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781   -0.2829    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1154    0.5683    1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    1.1068   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  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  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END

HMDB0013131
     RDKit          3D
3-Hydroxyhexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.0282   -1.0628   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205   -0.8925   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    0.3505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5220    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9329   -0.5689    0.6438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    0.9207   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857    1.0610   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2178    1.3898   -2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    0.8128   -0.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526    0.9373   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7590    2.0212    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.5922    2.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    1.1933    2.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518    1.5903    3.1496 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9715   -0.3979    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -0.6623   -0.0221 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8098   -0.9959   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.9125    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    0.2740    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -0.0627   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583   -1.4399    0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776   -1.7682   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -1.8064   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -0.7724   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2395    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.1777    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    1.3736    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -1.3992    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    0.0935   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7182    1.8837   -1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    1.2373   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    2.8740    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    2.3320    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.5623    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.1773   -0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768   -1.5336   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9878   -0.0858   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854   -1.6191   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.6839    1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -2.5959    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809   -2.2689    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781   -0.2829    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1154    0.5683    1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    1.1068   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  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  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END

HEADER    PROTEIN                                 25-FEB-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-21         0                                  
HETATM    1  C   UNK     0      -3.205  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.872  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.539  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.794  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.130  -0.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.463  -1.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.799  -0.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.132  -1.144   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.130   1.167   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.539   1.167   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.205   1.167   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -4.538   1.934   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0      -5.879   1.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.538   3.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.132   2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.523  -1.163   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.523  -2.702   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.190  -3.474   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      -5.857  -3.474   0.000  0.00  0.00           O+0
CONECT    1    2   11   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    3                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0013131
HETATM    1  C1  UNL     1       6.028  -1.063  -0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.520  -0.893  -0.389  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.102   0.350   0.373  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.619   0.522   0.171  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.933  -0.569   0.644  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.259   0.921  -1.227  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.786   1.061  -1.355  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.218   1.390  -2.410  1.00  0.00           O  
HETATM    9  O3  UNL     1       0.002   0.813  -0.241  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.453   0.937  -0.348  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.759   2.021   0.677  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.316   1.592   2.037  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.109   1.193   2.223  1.00  0.00           O  
HETATM   14  O5  UNL     1      -2.152   1.590   3.150  1.00  0.00           O1-
HETATM   15  C10 UNL     1      -1.972  -0.398   0.038  1.00  0.00           C  
HETATM   16  N1  UNL     1      -3.350  -0.662  -0.022  1.00  0.00           N1+
HETATM   17  C11 UNL     1      -3.810  -0.996  -1.375  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.559  -1.913   0.747  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.276   0.274   0.508  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.492  -0.063  -0.384  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.258  -1.440   0.848  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.478  -1.768  -0.892  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.034  -1.806  -0.010  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.385  -0.772  -1.477  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.642   1.239   0.022  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.312   0.178   1.445  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.331   1.374   0.870  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.058  -1.399   0.145  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.580   0.093  -1.921  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.718   1.884  -1.477  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.690   1.237  -1.370  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.077   2.874   0.396  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.795   2.332   0.740  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.657  -0.562   1.120  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.438  -1.177  -0.561  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.777  -1.534  -1.299  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.988  -0.086  -1.972  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.085  -1.619  -1.909  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.236  -1.684   1.800  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.768  -2.596   0.360  1.00  0.00           H  
HETATM   41  H22 UNL     1      -4.581  -2.269   0.654  1.00  0.00           H  
HETATM   42  H23 UNL     1      -5.278  -0.283   0.545  1.00  0.00           H  
HETATM   43  H24 UNL     1      -4.115   0.568   1.543  1.00  0.00           H  
HETATM   44  H25 UNL     1      -4.514   1.107  -0.208  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    6   27
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   15   31
CONECT   11   12   32   33
CONECT   12   13   13   14
CONECT   15   16   34   35
CONECT   16   17   18   19
CONECT   17   36   37   38
CONECT   18   39   40   41
CONECT   19   42   43   44
END

HMDB0013131
     RDKit          3D
3-Hydroxyhexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.0282   -1.0628   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205   -0.8925   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    0.3505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5220    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9329   -0.5689    0.6438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    0.9207   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857    1.0610   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2178    1.3898   -2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    0.8128   -0.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526    0.9373   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7590    2.0212    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.5922    2.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    1.1933    2.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518    1.5903    3.1496 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9715   -0.3979    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -0.6623   -0.0221 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8098   -0.9959   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.9125    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    0.2740    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -0.0627   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583   -1.4399    0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776   -1.7682   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -1.8064   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -0.7724   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2395    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.1777    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    1.3736    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -1.3992    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    0.0935   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7182    1.8837   -1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    1.2373   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    2.8740    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    2.3320    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.5623    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.1773   -0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768   -1.5336   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9878   -0.0858   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854   -1.6191   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.6839    1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -2.5959    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809   -2.2689    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781   -0.2829    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1154    0.5683    1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    1.1068   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  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  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₅NO₅

Average Molecular Weight

275.345

Monoisotopic Molecular Weight

275.173272909

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1469900-94-4

SMILES

CCC[C@H](O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C13H25NO5/c1-5-6-10(15)7-13(18)19-11(8-12(16)17)9-14(2,3)4/h10-11,15H,5-9H2,1-4H3/t10-,11+/m0/s1

InChI Key

VYEONLJQPYRKAN-WDEREUQCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0061633)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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	0.14 g/L	ALOGPS

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.749	30932474
DeepCCS	[M-H]-	172.795	30932474
DeepCCS	[M-2H]-	209.275	30932474
DeepCCS	[M+Na]+	185.481	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyhexanoycarnitine	CCCC(O)CC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	2704.3	Standard polar	33892256
Hydroxyhexanoycarnitine	CCCC(O)CC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1576.6	Standard non polar	33892256
Hydroxyhexanoycarnitine	CCCC(O)CC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1844.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyhexanoycarnitine,1TMS,isomer #1	CCCC(CC(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	1850.9	Semi standard non polar	33892256
Hydroxyhexanoycarnitine,1TBDMS,isomer #1	CCCC(CC(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	2085.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhexanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhexanoylcarnitine 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 - 3-Hydroxyhexanoylcarnitine 10V, Positive-QTOF	splash10-004i-0090000000-5cb04a799cb41586c48e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexanoylcarnitine 20V, Positive-QTOF	splash10-002r-9050000000-6d47d6e1afdb843ffb9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Saliva
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	Adult (>18 years old)	Both	Normal	32966057	details
Saliva	Detected and Quantified	0.035 +/- 0.0003 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB029304

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

156908002

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

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Esperanza MG, Wrobel K, Ojeda AG, Garay-Sevilla ME, Escobosa ARC, Barrientos EY, Wrobel K: Liquid chromatography-mass spectrometry untargeted metabolomics reveals increased levels of tryptophan indole metabolites in urine of metabolic syndrome patients. Eur J Mass Spectrom (Chichester). 2020 Dec;26(6):379-387. doi: 10.1177/1469066720964632. Epub 2020 Oct 8. [PubMed:33295818 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
The AOCS Lipid Library [Link]

Showing metabocard for 3-Hydroxyhexanoylcarnitine (HMDB0013131)

MOL for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

3D MOL for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

3D SDF for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

3D-SDF for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

PDB for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

3D PDB for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

SMILES for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

INCHI for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

Structure for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

3D Structure for HMDB0013131 (3-Hydroxyhexanoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra