NP-MRD: Showing NP-Card for Hexanoylcarnitine (NP0000236)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:43:56 UTC

NP-MRD ID

NP0000236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hexanoylcarnitine

Description

Hexanoylcarnitine (CAS: 6418-78-6), Also known as caproylcarnitine, is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism 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. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physicochemical properties as well. 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.). 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.

Structure

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

NP0001092
     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    5.7405   -1.6036    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8470   -0.2087   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049    0.6693    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.0968   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.9446    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424    0.3757   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -0.7056   -0.7945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674    0.9655    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5252    0.4283   -0.2982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2174    1.4583   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986    1.8966   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    2.7592   -3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    1.3624   -2.6371 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2992    0.0692    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -0.4931    0.7353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6455    0.4280    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.5250   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.2255    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3192   -1.5500    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7568   -2.0645    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -2.2189   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -0.3031   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    0.2217    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    1.6541   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.7817    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9459    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.0837   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897    1.9814   -0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431    0.9727    1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -0.4639   -0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    2.4076   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    1.0768   -1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -0.7174    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685    0.9570    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4710    0.3207    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    0.1865   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.4925    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -1.9550   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.1580   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -2.3853   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759   -0.4290    2.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.9760    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -1.6621    2.3588 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  6
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  CHG  2  13  -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>
NP0000236

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0001092
     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    5.7405   -1.6036    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8470   -0.2087   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049    0.6693    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.0968   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.9446    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424    0.3757   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -0.7056   -0.7945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674    0.9655    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5252    0.4283   -0.2982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2174    1.4583   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986    1.8966   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    2.7592   -3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    1.3624   -2.6371 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2992    0.0692    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -0.4931    0.7353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6455    0.4280    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.5250   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.2255    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3192   -1.5500    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7568   -2.0645    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -2.2189   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -0.3031   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    0.2217    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    1.6541   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.7817    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9459    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.0837   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897    1.9814   -0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431    0.9727    1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -0.4639   -0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    2.4076   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    1.0768   -1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -0.7174    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685    0.9570    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4710    0.3207    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    0.1865   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.4925    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -1.9550   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.1580   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -2.3853   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759   -0.4290    2.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.9760    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -1.6621    2.3588 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  6
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  CHG  2  13  -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    NP0001092
HETATM    1  C1  UNL     1       5.741  -1.604   0.439  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.847  -0.209  -0.119  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.705   0.669   0.332  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.402   0.097  -0.118  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.243   0.945   0.313  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.942   0.376  -0.135  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.993  -0.706  -0.795  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.267   0.965   0.135  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.525   0.428  -0.298  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.217   1.458  -1.121  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.499   1.897  -2.326  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.009   2.759  -3.069  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.272   1.362  -2.637  1.00  0.00           O1-
HETATM   14  C10 UNL     1      -2.299   0.069   0.952  1.00  0.00           C  
HETATM   15  N1  UNL     1      -3.589  -0.493   0.735  1.00  0.00           N1+
HETATM   16  C11 UNL     1      -4.645   0.428   0.509  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.601  -1.525  -0.302  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.912  -1.225   1.978  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.319  -1.550   1.450  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.757  -2.065   0.453  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.059  -2.219  -0.173  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.822  -0.303  -1.227  1.00  0.00           H  
HETATM   23  H5  UNL     1       6.824   0.222   0.188  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.845   1.654  -0.175  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.777   0.782   1.432  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.312  -0.946   0.242  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.404   0.084  -1.234  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.390   1.981  -0.012  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.243   0.973   1.441  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.292  -0.464  -0.899  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.407   2.408  -0.532  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.213   1.077  -1.504  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.680  -0.717   1.475  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.368   0.957   1.597  1.00  0.00           H  
HETATM   35  H17 UNL     1      -5.471   0.321   1.272  1.00  0.00           H  
HETATM   36  H18 UNL     1      -5.171   0.186  -0.459  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.375   1.493   0.545  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.611  -1.955  -0.491  1.00  0.00           H  
HETATM   39  H21 UNL     1      -4.018  -1.158  -1.260  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.250  -2.385  -0.004  1.00  0.00           H  
HETATM   41  H23 UNL     1      -4.276  -0.429   2.679  1.00  0.00           H  
HETATM   42  H24 UNL     1      -4.689  -1.976   1.766  1.00  0.00           H  
HETATM   43  H25 UNL     1      -2.966  -1.662   2.359  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   14   15   33   34
CONECT   15   16   17   18
CONECT   16   35   36   37
CONECT   17   38   39   40
CONECT   18   41   42   43
END

NP0001092
     RDKit          3D

43 42  0  0  0  0  0  0  0  0999 V2000
    5.7405   -1.6036    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8470   -0.2087   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049    0.6693    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.0968   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.9446    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424    0.3757   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -0.7056   -0.7945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674    0.9655    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5252    0.4283   -0.2982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2174    1.4583   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986    1.8966   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    2.7592   -3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    1.3624   -2.6371 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2992    0.0692    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -0.4931    0.7353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6455    0.4280    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.5250   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.2255    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3192   -1.5500    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7568   -2.0645    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -2.2189   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -0.3031   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    0.2217    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    1.6541   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.7817    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9459    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.0837   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897    1.9814   -0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431    0.9727    1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -0.4639   -0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    2.4076   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    1.0768   -1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -0.7174    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685    0.9570    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4710    0.3207    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    0.1865   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.4925    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -1.9550   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.1580   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -2.3853   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759   -0.4290    2.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.9760    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -1.6621    2.3588 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  6
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  CHG  2  13  -1  15   1
M  END

View in JSmol View NMR Assignments

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

C₁₃H₂₅NO₄

Average Mass

259.3419 Da

Monoisotopic Mass

259.17836 Da

IUPAC Name

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

Traditional Name

L-carnitine hexanoyl ester

CAS Registry Number

6418-78-6

SMILES

CCCCCC(=O)OC(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

InChI Key

VVPRQWTYSNDTEA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudo-nitzschia multistriata	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000756

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

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 ]
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 ]

Showing NP-Card for Hexanoylcarnitine (NP0000236)

MOL for NP0000236 (Hexanoylcarnitine)

3D MOL for NP0000236 (Hexanoylcarnitine)

3D SDF for NP0000236 (Hexanoylcarnitine)

3D-SDF for NP0000236 (Hexanoylcarnitine)

PDB for NP0000236 (Hexanoylcarnitine)

3D PDB for NP0000236 (Hexanoylcarnitine)

SMILES for NP0000236 (Hexanoylcarnitine)

INCHI for NP0000236 (Hexanoylcarnitine)

Structure for NP0000236 (Hexanoylcarnitine)

3D Structure for NP0000236 (Hexanoylcarnitine)