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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:06 UTC

HMDB ID

HMDB0000756

Secondary Accession Numbers

HMDB0000705
HMDB00705
HMDB00756

Metabolite Identification

Common Name

Hexanoylcarnitine

Description

Hexanoylcarnitine (CAS: 6418-78-6), also known as caproylcarnitine, is an acylcarnitine. Acylcarnitines are the product of the conjugation of carnitine with acyl-coenzyme A, that allows the transport of fatty acids across mitochondrial membranes. Long or medium chain fatty acids are then oxidized in the mitochondria for energy production. The ionic nature of L-carnitine causes high water solubility which decreases with increasing chain lengths of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined not only by their function but also by their physicochemical properties. Hexanoylcarnitine is a medium-chain acylcarnitine present in the urine of patients with medium-chain acyl-CoA dehydrogenase deficiency (PMID: 1635814 ). Hexanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II which are both inborn errors of metabolism. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism, which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. High-performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).

Structure

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

HMDB0000756
     RDKit          3D
Hexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.4587   -0.1717   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.2445   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.4693    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370    0.4650    0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -0.9557    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135   -0.8404    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3869   -1.0973    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.4730   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3647   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8522   -1.2446   -1.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.6344   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -3.0930   -0.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575   -3.5500   -2.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    0.9941   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.1685   -0.1299 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9157    1.5334   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.1032    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6452    2.3633    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7843   -0.7047    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486    0.8885   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8825   -0.6679   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -1.3298   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    0.1636   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501    0.0550    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.5594    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.0087   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    1.0589    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -1.5065    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823   -1.4563   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -0.7809    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -0.9197   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9597   -1.2680   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -4.1328   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.7565    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224    1.3654   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    2.5086   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    0.7767   -2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6724   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.5158    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963   -0.7298    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8978   -0.2581   -0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    3.0211    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518    2.0358    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    2.9405    0.9242 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
M  CHG  1  15   1
M  END


  Mrv1652311011918172D          

 18 17  0  0  0  0            999 V2000
10002.564410004.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.278810003.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706810003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136710003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852610004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.566510003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110004.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.564410004.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310005.3126    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.131910004.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310006.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.996810005.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.858410003.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.858410002.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.572810002.4154    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10001.144110002.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  6  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  CHG  2  11   1  17  -1
M  END
> <DATABASE_ID>
HMDB0000756

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1

> <INCHI_KEY>
VVPRQWTYSNDTEA-LLVKDONJSA-N

> <FORMULA>
C13H25NO4

> <MOLECULAR_WEIGHT>
259.3419

> <EXACT_MASS>
259.178358293

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.79200276844265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.68

> <JCHEM_LOGP>
-2.4121387958050784

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0571868789043

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
91.0667

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-carnitine hexanoyl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000756
     RDKit          3D
Hexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.4587   -0.1717   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.2445   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.4693    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370    0.4650    0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -0.9557    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135   -0.8404    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3869   -1.0973    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.4730   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3647   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8522   -1.2446   -1.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.6344   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -3.0930   -0.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575   -3.5500   -2.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    0.9941   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.1685   -0.1299 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9157    1.5334   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.1032    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6452    2.3633    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7843   -0.7047    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486    0.8885   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8825   -0.6679   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -1.3298   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    0.1636   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501    0.0550    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.5594    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.0087   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    1.0589    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -1.5065    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823   -1.4563   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -0.7809    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -0.9197   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9597   -1.2680   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -4.1328   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.7565    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224    1.3654   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    2.5086   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    0.7767   -2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6724   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.5158    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963   -0.7298    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8978   -0.2581   -0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    3.0211    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518    2.0358    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    2.9405    0.9242 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
M  CHG  1  15   1
M  END

HEADER    PROTEIN                                 01-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-NOV-19         0                                  
HETATM    1  C   UNK     0    8671.4548674.278   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8672.7878673.506   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8674.1208674.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8675.4538673.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8676.7898674.278   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.1228673.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8679.4588674.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8680.7918673.506   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8674.1208675.817   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8671.4548675.817   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8670.1218676.584   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0    8668.7808675.813   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.1218678.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.5278677.504   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.1368673.487   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.1368671.947   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8671.4698671.175   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0    8668.8028671.175   0.000  0.00  0.00           O+0
CONECT    1    2   10   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    1   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0000756
HETATM    1  C1  UNL     1       6.459  -0.172  -0.754  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.943  -0.245  -0.757  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.447   0.469   0.471  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.937   0.465   0.584  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.385  -0.956   0.635  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.914  -0.840   0.778  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.387  -1.097   1.867  1.00  0.00           O  
HETATM    8  O2  UNL     1       0.040  -0.473  -0.178  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.348  -0.365  -0.111  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.852  -1.245  -1.212  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.419  -2.634  -1.006  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.790  -3.093  -0.044  1.00  0.00           O  
HETATM   13  O4  UNL     1      -1.758  -3.550  -2.019  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.914   0.994  -0.225  1.00  0.00           C  
HETATM   15  N1  UNL     1      -3.333   1.169  -0.130  1.00  0.00           N1+
HETATM   16  C11 UNL     1      -3.916   1.533  -1.439  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.117   0.103   0.370  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.645   2.363   0.700  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.784  -0.705   0.174  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.749   0.889  -0.632  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.883  -0.668  -1.637  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.668  -1.330  -0.654  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.488   0.164  -1.662  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.850   0.055   1.402  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.745   1.559   0.410  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.513   1.009  -0.301  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.665   1.059   1.476  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.843  -1.506   1.483  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.682  -1.456  -0.285  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.635  -0.781   0.857  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.381  -0.920  -2.194  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.960  -1.268  -1.325  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.561  -4.133  -1.998  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.447   1.757   0.434  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.622   1.365  -1.258  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.493   2.509  -1.752  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.789   0.777  -2.200  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.988   1.672  -1.237  1.00  0.00           H  
HETATM   39  H21 UNL     1      -4.764   0.516   1.209  1.00  0.00           H  
HETATM   40  H22 UNL     1      -3.596  -0.730   0.864  1.00  0.00           H  
HETATM   41  H23 UNL     1      -4.898  -0.258  -0.348  1.00  0.00           H  
HETATM   42  H24 UNL     1      -4.376   3.021   0.248  1.00  0.00           H  
HETATM   43  H25 UNL     1      -4.052   2.036   1.695  1.00  0.00           H  
HETATM   44  H26 UNL     1      -2.727   2.941   0.924  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   14   30
CONECT   10   11   31   32
CONECT   11   12   12   13
CONECT   13   33
CONECT   14   15   34   35
CONECT   15   16   17   18
CONECT   16   36   37   38
CONECT   17   39   40   41
CONECT   18   42   43   44
END

HMDB0000756
     RDKit          3D
Hexanoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    6.4587   -0.1717   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.2445   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.4693    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370    0.4650    0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -0.9557    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135   -0.8404    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3869   -1.0973    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.4730   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3647   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8522   -1.2446   -1.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.6344   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -3.0930   -0.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575   -3.5500   -2.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    0.9941   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.1685   -0.1299 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9157    1.5334   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.1032    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6452    2.3633    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7843   -0.7047    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486    0.8885   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8825   -0.6679   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -1.3298   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    0.1636   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501    0.0550    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.5594    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.0087   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    1.0589    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -1.5065    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823   -1.4563   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -0.7809    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -0.9197   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9597   -1.2680   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -4.1328   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.7565    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224    1.3654   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    2.5086   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    0.7767   -2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6724   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.5158    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963   -0.7298    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8978   -0.2581   -0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    3.0211    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518    2.0358    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    2.9405    0.9242 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
M  CHG  1  15   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Caproylcarnitine	ChEBI
(R)-Hexanoylcarnitine	ChEBI
Hexanoyl-L-carnitine	ChEBI
L-Hexanoylcarnitine	ChEBI
O-Hexanoyl-(R)-carnitine	ChEBI
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-propanaminium inner salt	HMDB
Hexanoate	HMDB
Hexanoic acid	HMDB
Hexanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
L-Carnitine hexanoyl ester	HMDB
L-Hexanoate	HMDB
L-Hexanoic acid	HMDB
L-Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
C6 Carnitine	HMDB
Hexanoylcarnitine	HMDB

Chemical Formula

C₁₃H₂₆NO₄

Average Molecular Weight

260.3498

Monoisotopic Molecular Weight

260.186183325

IUPAC Name

(3R)-3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

L-carnitine hexanoyl ester

CAS Registry Number

22671-29-0

SMILES

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

InChI Identifier

InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/p+1/t11-/m1/s1

InChI Key

VVPRQWTYSNDTEA-LLVKDONJSA-O

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
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:84834 )
Fatty acyl carnitines (LMFA07070001 )

Ontology

Placenta (HMDB: HMDB0000756)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 16425363)

Excreta

Urine (PMID: 24023812)
Feces (PMID: 27609529)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000756)

Source

Endogenous

Endogenous (HMDB: HMDB0000756)

Animal

Animal (HMDB: HMDB0000756)

Exogenous

Food

Food (HMDB: HMDB0000756)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000756)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000756)

Cellular process

Cell signaling (HMDB: HMDB0000756)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000756)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000756)
Energy source (PMID: 35710135)

Nutrient

Nutrient (HMDB: HMDB0000756)

Industrial application

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	0.0043 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.4	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	28.79 Å³	ChemAxon
Number of Rings	0	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]+	164.802	30932474
DeepCCS	[M-H]-	162.444	30932474
DeepCCS	[M-2H]-	195.328	30932474
DeepCCS	[M+Na]+	170.896	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexanoylcarnitine	CCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2699.0	Standard polar	33892256
Hexanoylcarnitine	CCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1539.5	Standard non polar	33892256
Hexanoylcarnitine	CCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1772.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexanoylcarnitine,1TMS,isomer #1	CCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	1808.0	Semi standard non polar	33892256
Hexanoylcarnitine,1TBDMS,isomer #1	CCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	2035.1	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 - Hexanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylcarnitine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylcarnitine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylcarnitine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03dr-6090000000-c19afe5acca5a4b0f82f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylcarnitine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9000000000-8d30a3ad5fce9bf004f7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylcarnitine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-a38bcb0bb25abdcaaa7c	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylcarnitine 10V, Positive-QTOF	splash10-03di-0090000000-5c4e7ecd71d0ed800ae6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylcarnitine 20V, Positive-QTOF	splash10-01p9-9050000000-f92580b9643caf52768e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.080 +/- 0.006 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.020-0.130 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	<0.12 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Blood	Detected and Quantified	0.06 +/- 0.02 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.020-0.130 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.031 (0.015-0.053) uM	Children (1-13 years old)	Both	Normal	9034211	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected and Quantified	0.23 +/- 0.13 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.18 +/- 0.08 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.02-0.05 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.03 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.03 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.05 (0.03-0.07) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.060 +/- 0.004 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details
Blood	Detected and Quantified	0.18 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.31 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.051 +/- 0.016 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.058 +/- 0.025 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.001 (0.0-0.004) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Celiac disease
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Glutaric aciduria II
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
231680 (Glutaric aciduria II)
601665 (Obesity)
266600 (Crohn's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022226

KNApSAcK ID

C00052313

Chemspider ID

2497478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3548

PubChem Compound

3246938

PDB ID

Not Available

ChEBI ID

84834

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000244

Good Scents ID

Not Available

References

Synthesis Reference

Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko. Synthesis of acylcarnitines for differential diagnosis of metabolic disorders. Nippon Iyo Masu Supekutoru Gakkai Koenshu (1993), 18 129-32.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ziadeh R, Hoffman EP, Finegold DN, Hoop RC, Brackett JC, Strauss AW, Naylor EW: Medium chain acyl-CoA dehydrogenase deficiency in Pennsylvania: neonatal screening shows high incidence and unexpected mutation frequencies. Pediatr Res. 1995 May;37(5):675-8. [PubMed:7603790 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Minkler PE, Hoppel CL: Quantification of free carnitine, individual short- and medium-chain acylcarnitines, and total carnitine in plasma by high-performance liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):510-8. [PubMed:8214594 ]
Chalmers RA, Roe CR, Stacey TE, Hoppel CL: Urinary excretion of l-carnitine and acylcarnitines by patients with disorders of organic acid metabolism: evidence for secondary insufficiency of l-carnitine. Pediatr Res. 1984 Dec;18(12):1325-8. [PubMed:6441143 ]
Fontaine M, Briand G, Vallee L, Ricart G, Degand P, Divry P, Vianey-Saban C, Vamecq J: Acylcarnitine removal in a patient with acyl-CoA beta-oxidation deficiency disorder: effect of L-carnitine therapy and starvation. Clin Chim Acta. 1996 Aug 30;252(2):109-22. [PubMed:8853559 ]
Lee PJ, Harrison EL, Jones MG, Jones S, Leonard JV, Chalmers RA: L-carnitine and exercise tolerance in medium-chain acyl-coenzyme A dehydrogenase (MCAD) deficiency: a pilot study. J Inherit Metab Dis. 2005;28(2):141-52. [PubMed:15877203 ]
Tyni T, Pourfarzam M, Turnbull DM: Analysis of mitochondrial fatty acid oxidation intermediates by tandem mass spectrometry from intact mitochondria prepared from homogenates of cultured fibroblasts, skeletal muscle cells, and fresh muscle. Pediatr Res. 2002 Jul;52(1):64-70. [PubMed:12084849 ]
Caksen H, Tuncer O, Kirimi E, Fryns JP, Uner A, Unal O, Cinal A, Odabas D: Report of two Turkish infants with Norman-Roberts syndrome. Genet Couns. 2004;15(1):9-17. [PubMed:15083694 ]
Schmidt-Sommerfeld E, Penn D, Rinaldo P, Kossak D, Li BU, Huang ZH, Gage DA: Urinary medium-chain acylcarnitines in medium-chain acyl-CoA dehydrogenase deficiency, medium-chain triglyceride feeding and valproic acid therapy: sensitivity and specificity of the radioisotopic exchange/high performance liquid chromatography method. Pediatr Res. 1992 Jun;31(6):545-51. [PubMed:1635814 ]
Shigematsu Y, Hata I, Nakai A, Kikawa Y, Sudo M, Tanaka Y, Yamaguchi S, Jakobs C: Prenatal diagnosis of organic acidemias based on amniotic fluid levels of acylcarnitines. Pediatr Res. 1996 Apr;39(4 Pt 1):680-4. [PubMed:8848345 ]
Schmidt-Sommerfeld E, Penn D, Duran M, Bennett MJ, Santer R, Stanley CA: Detection of inborn errors of fatty acid oxidation from acylcarnitine analysis of plasma and blood spots with the radioisotopic exchange-high-performance liquid chromatographic method. J Pediatr. 1993 May;122(5 Pt 1):708-14. [PubMed:8496747 ]
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Bennett MJ, Coates PM, Hale DE, Millington DS, Pollitt RJ, Rinaldo P, Roe CR, Tanaka K: Analysis of abnormal urinary metabolites in the newborn period in medium-chain acyl-CoA dehydrogenase deficiency. J Inherit Metab Dis. 1990;13(5):707-15. [PubMed:2246856 ]
Vallee L, Fontaine M, Nuyts JP, Ricart G, Krivosic I, Divry P, Vianey-Saban C, Lhermitte M, Vamecq J: Stroke, hemiparesis and deficient mitochondrial beta-oxidation. Eur J Pediatr. 1994 Aug;153(8):598-603. [PubMed:7957409 ]
Schmidt-Sommerfeld E, Penn D, Kerner J, Bieber LL, Rossi TM, Lebenthal E: Quantitation of urinary carnitine esters in a patient with medium-chain acyl-coenzyme A dehydrogenase deficiency: effect of metabolic state and L-carnitine therapy. J Pediatr. 1989 Oct;115(4):577-82. [PubMed:2795349 ]
Minkler PE, Hoppel CL: Quantification of carnitine and specific acylcarnitines by high-performance liquid chromatography: application to normal human urine and urine from patients with methylmalonic aciduria, isovaleric acidemia or medium-chain acyl-CoA dehydrogenase deficiency. J Chromatogr. 1993 Apr 2;613(2):203-21. [PubMed:8491807 ]
Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. [PubMed:17508264 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Hexanoylcarnitine (HMDB0000756)

MOL for HMDB0000756 (Hexanoylcarnitine)

3D MOL for HMDB0000756 (Hexanoylcarnitine)

3D SDF for HMDB0000756 (Hexanoylcarnitine)

3D-SDF for HMDB0000756 (Hexanoylcarnitine)

PDB for HMDB0000756 (Hexanoylcarnitine)

3D PDB for HMDB0000756 (Hexanoylcarnitine)

SMILES for HMDB0000756 (Hexanoylcarnitine)

INCHI for HMDB0000756 (Hexanoylcarnitine)

Structure for HMDB0000756 (Hexanoylcarnitine)

3D Structure for HMDB0000756 (Hexanoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra