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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2025-05-29 22:15:42 UTC

HMDB ID

HMDB0000791

Secondary Accession Numbers

HMDB0000834
HMDB00791
HMDB00834

Metabolite Identification

Common Name

Octanoylcarnitine

Description

L-Octanoylcarnitine is the physiologically active form of octanoylcarnitine (PMID: 11274033 ). Octanoylcarnitine is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD is characterized by an intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels (OMIM: 201450 ). L-Octanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II, which are inborn errors of metabolism.

Structure

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

HMDB0000791
     RDKit          3D
Octanoylcarnitine
 50 49  0  0  0  0  0  0  0  0999 V2000
    5.8644   -1.5289   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -0.2004    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    0.6000   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -0.2312   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568    0.4288   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    1.7693   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    1.6479    0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    0.8574    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.4174    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3734    0.6070    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5989   -0.2055    0.4485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4008   -1.4287   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355   -2.5289   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -2.6892    0.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -3.4909   -1.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    0.7491    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.4564    0.1801 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.5461   -0.2779   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840    1.7701    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4357   -0.0292    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240   -1.8430   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739   -2.2713   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912   -1.3702   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6963    0.3821    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620   -0.3955    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155    1.5531    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9318    0.7324   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.4307    0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -1.1990   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.2177   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    0.6215   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    2.2295   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    2.4607   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.1722    1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672    2.6770    1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.4250    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395   -1.1587   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -1.8599   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -4.4647   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4908    1.7070    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4551    1.1183   -1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0621   -1.2113   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7202   -0.4429   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    0.3052   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5299    2.3866    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709    2.2429   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8435    1.4552    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167    0.7419    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -0.8939    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938   -0.2944    2.0158 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  1
 12 37  1  0
 12 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
M  CHG  1  17   1
M  END


  Mrv1652303062019112D          

 20 19  0  0  0  0            999 V2000
 9999.133810001.3705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.847810000.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.562110001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.276510000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.990110001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.706010000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.419910001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.135810000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.849610001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.563510000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.562110002.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.133810002.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.419510002.6057    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.701110002.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.419510003.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.566010003.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.427610000.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.427610000.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1418 9999.7086    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.7133 9999.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  6  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  CHG  2  13   1  19  -1
M  END
> <DATABASE_ID>
HMDB0000791

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1

> <INCHI_KEY>
CXTATJFJDMJMIY-CYBMUJFWSA-N

> <FORMULA>
C15H29NO4

> <MOLECULAR_WEIGHT>
287.3951

> <EXACT_MASS>
287.209658421

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.279951202307146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-1.5230014658050801

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.05718689202227

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
100.2687

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-octanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000791
     RDKit          3D
Octanoylcarnitine
 50 49  0  0  0  0  0  0  0  0999 V2000
    5.8644   -1.5289   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -0.2004    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    0.6000   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -0.2312   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568    0.4288   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    1.7693   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    1.6479    0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    0.8574    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.4174    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3734    0.6070    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5989   -0.2055    0.4485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4008   -1.4287   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355   -2.5289   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -2.6892    0.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -3.4909   -1.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    0.7491    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.4564    0.1801 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.5461   -0.2779   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840    1.7701    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4357   -0.0292    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240   -1.8430   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739   -2.2713   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912   -1.3702   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6963    0.3821    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620   -0.3955    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155    1.5531    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9318    0.7324   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.4307    0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -1.1990   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.2177   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    0.6215   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    2.2295   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    2.4607   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.1722    1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672    2.6770    1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.4250    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395   -1.1587   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -1.8599   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -4.4647   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4908    1.7070    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4551    1.1183   -1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0621   -1.2113   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7202   -0.4429   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    0.3052   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5299    2.3866    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709    2.2429   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8435    1.4552    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167    0.7419    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -0.8939    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938   -0.2944    2.0158 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  1
 12 37  1  0
 12 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
M  CHG  1  17   1
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.0508669.225   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.3838668.453   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8667.7168669.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.0498668.453   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.3828669.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.7188668.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.0508669.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.3878668.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8675.7198669.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8677.0528668.453   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.7168670.764   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8665.0508670.764   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8663.7168671.531   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0    8662.3758670.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.7168673.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.1238672.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.7328668.434   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.7328666.894   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8665.0658666.123   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0    8662.3988666.123   0.000  0.00  0.00           O+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0000791
HETATM    1  C1  UNL     1       5.864  -1.529  -0.523  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.770  -0.200   0.207  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.676   0.600  -0.517  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.426  -0.231  -0.394  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.257   0.429  -1.080  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.006   1.769  -0.468  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.699   1.648   0.987  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.473   0.857   1.183  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.217   0.417   2.325  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.373   0.607   0.149  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.599  -0.206   0.448  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.401  -1.429  -0.376  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.336  -2.529  -0.305  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.183  -2.689   0.582  1.00  0.00           O  
HETATM   15  O4  UNL     1      -2.269  -3.491  -1.331  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.658   0.749   0.035  1.00  0.00           C  
HETATM   17  N1  UNL     1      -4.036   0.456   0.180  1.00  0.00           N1+
HETATM   18  C13 UNL     1      -4.546  -0.278  -0.952  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.784   1.770   0.081  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.436  -0.029   1.464  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.924  -1.843  -0.458  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.174  -2.271  -0.073  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.591  -1.370  -1.584  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.696   0.382   0.164  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.462  -0.395   1.254  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.516   1.553   0.043  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.932   0.732  -1.572  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.256  -0.431   0.680  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.656  -1.199  -0.924  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.362  -0.218  -1.004  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.487   0.622  -2.161  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.161   2.229  -1.039  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.873   2.461  -0.650  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.503   1.172   1.573  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.567   2.677   1.461  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.536  -0.425   1.498  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.140  -1.159  -1.448  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.398  -1.860  -0.022  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.335  -4.465  -1.025  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.491   1.707   0.641  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.455   1.118  -1.012  1.00  0.00           H  
HETATM   42  H22 UNL     1      -5.062  -1.211  -0.699  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.720  -0.443  -1.704  1.00  0.00           H  
HETATM   44  H24 UNL     1      -5.307   0.305  -1.554  1.00  0.00           H  
HETATM   45  H25 UNL     1      -4.530   2.387   0.967  1.00  0.00           H  
HETATM   46  H26 UNL     1      -4.571   2.243  -0.874  1.00  0.00           H  
HETATM   47  H27 UNL     1      -5.844   1.455   0.172  1.00  0.00           H  
HETATM   48  H28 UNL     1      -4.917   0.742   2.093  1.00  0.00           H  
HETATM   49  H29 UNL     1      -5.129  -0.894   1.417  1.00  0.00           H  
HETATM   50  H30 UNL     1      -3.494  -0.294   2.016  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   16   36
CONECT   12   13   37   38
CONECT   13   14   14   15
CONECT   15   39
CONECT   16   17   40   41
CONECT   17   18   19   20
CONECT   18   42   43   44
CONECT   19   45   46   47
CONECT   20   48   49   50
END

HMDB0000791
     RDKit          3D
Octanoylcarnitine
 50 49  0  0  0  0  0  0  0  0999 V2000
    5.8644   -1.5289   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -0.2004    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    0.6000   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -0.2312   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568    0.4288   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    1.7693   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    1.6479    0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    0.8574    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.4174    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3734    0.6070    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5989   -0.2055    0.4485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4008   -1.4287   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355   -2.5289   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -2.6892    0.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -3.4909   -1.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    0.7491    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.4564    0.1801 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.5461   -0.2779   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840    1.7701    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4357   -0.0292    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240   -1.8430   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739   -2.2713   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912   -1.3702   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6963    0.3821    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620   -0.3955    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155    1.5531    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9318    0.7324   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.4307    0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -1.1990   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.2177   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    0.6215   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    2.2295   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    2.4607   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.1722    1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672    2.6770    1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.4250    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395   -1.1587   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -1.8599   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -4.4647   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4908    1.7070    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4551    1.1183   -1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0621   -1.2113   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7202   -0.4429   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    0.3052   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5299    2.3866    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709    2.2429   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8435    1.4552    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167    0.7419    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -0.8939    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938   -0.2944    2.0158 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  1
 12 37  1  0
 12 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
M  CHG  1  17   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Octanoyl-L-carnitine	ChEBI
O-Octanoyl-(R)-carnitine	ChEBI
O-Octanoyl-R-carnitine	ChEBI
(-)-Octanoylcarnitine	HMDB
L-Carnitine octanoyl ester	HMDB
L-O-Octanoylcarnitine	HMDB
Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
Octanoyl-L-carnitine	HMDB
Octanoylcarnitine	HMDB
Octanoylcarnitine chloride, (R)-isomer	HMDB
Octanoylcarnitine, (R)-isomer	HMDB
Octanoylcarnitine chloride	HMDB
Octanoylcarnitine chloride, (+-)-isomer	HMDB
Octanoylcarnitine, (+-)-isomer	HMDB
C8-Carnitine	HMDB
L-Octanoylcarnitine	ChEBI

Chemical Formula

C₁₅H₂₉NO₄

Average Molecular Weight

287.3951

Monoisotopic Molecular Weight

287.209658421

IUPAC Name

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

Traditional Name

L-octanoylcarnitine

CAS Registry Number

25243-95-2

SMILES

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

InChI Identifier

InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1

InChI Key

CXTATJFJDMJMIY-CYBMUJFWSA-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
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-octanoylcarnitine (CHEBI:18102 )
O-acyl-L-carnitine (CHEBI:18102 )
Fatty acyl carnitines (C02838 )
Fatty acyl carnitines (LMFA07070002 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Celiac disease (HMDB: HMDB0000791)

Genetic disorder

Inborn errors of metabolism

Very Long Chain Acyl-CoA Dehydrogenase Deficiency (HMDB: HMDB0000791)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000791)

Organ

Placenta (HMDB: HMDB0000791)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 17314143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000791)

Source

Endogenous

Endogenous (HMDB: HMDB0000791)

Animal

Animal (HMDB: HMDB0000791)

Exogenous

Food

Food (HMDB: HMDB0000791)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0000791)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000791)

Biochemical pathway

Metabolic pathway

Lipid metabolism pathway (HMDB: HMDB0000791)

Cellular process

Cell signaling (HMDB: HMDB0000791)

Biochemical process

Lipid transport (HMDB: HMDB0000791)

Role

Biological role

Energy source (HMDB: HMDB0000791)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000791)

Pharmaceutical industry

Biomarker

Obesity (MarkerDB: MDB00000253)
Celiac disease (MarkerDB: MDB00000253)
Glutaric Acidemia Type 2 (MarkerDB: MDB00000253)

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	0.00085 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.5	ChemAxon
logS	-5.6	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	12	ChemAxon
Refractivity	100.27 m³·mol⁻¹	ChemAxon
Polarizability	33.28 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]+	173.609	30932474
DeepCCS	[M-H]-	171.251	30932474
DeepCCS	[M-2H]-	204.134	30932474
DeepCCS	[M+Na]+	180.175	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	179.2	32859911
AllCCS	[M+Na-2H]-	180.3	32859911
AllCCS	[M+HCOO]-	181.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.5 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4394 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.56 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Octanoylcarnitine	CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2909.6	Standard polar	33892256
Octanoylcarnitine	CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1720.4	Standard non polar	33892256
Octanoylcarnitine	CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1975.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Octanoylcarnitine,1TMS,isomer #1	CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2013.7	Semi standard non polar	33892256
Octanoylcarnitine,1TBDMS,isomer #1	CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	2237.7	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 - Octanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octanoylcarnitine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octanoylcarnitine 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 - Octanoylcarnitine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-6090000000-f5427438c18b619c6d12	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octanoylcarnitine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9000000000-0ffd63a09867f6b170e5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octanoylcarnitine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-558ce1fa555823e95479	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octanoylcarnitine 10V, Positive-QTOF	splash10-000i-0090000000-9c0281b8f2959b51e65e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octanoylcarnitine 20V, Positive-QTOF	splash10-000i-9050000000-5fd4264c445d0a035113	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.061 (0.006-0.127) uM	Children (1-13 years old)	Both	Normal	9034211	details
Blood	Detected and Quantified	0.07 ± 0.04 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.15 ± 0.1 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.14 ± 0.07 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.06 ± 0.02 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.11 ± 0.07 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.1 ± 0.05 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.06 ± 0.02 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.1 ± 0.05 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.09 ± 0.05 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.17-0.50 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.17-0.50 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.121 +/- 0.009 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.23 +/- 0.08 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.18 +/- 0.07 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	<0.22 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Blood	Detected and Quantified	0.21(0.06) uM	Adult (>18 years old)	Both	Normal	26010610	details
Feces	Detected and Quantified	1.1 +/- 0.52 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.74 +/- 0.32 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	0-4871.343 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Urine	Detected and Quantified	0.02-0.31 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.05(0.02-0.37) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.04(0.02-0.09) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.05 (0.04-0.09) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.05 (0.03-0.09) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	60.81 +/- 2.32 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.025 (0.014-0.034) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Blood	Detected and Quantified	0.160 +/- 0.069 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.140 +/- 0.033 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.59 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.37 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.26(0.08) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.1304 (0.0496) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.0943 (0.04369) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.086 +/- 0.006 uM	Adult (>18 years old)	Both	Celiac disease	16425363	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	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	Crohns disease	27609529	details
Feces	Detected and Quantified	0-11899.994 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	14.246-418.887 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	6434845	details
Urine	Detected and Quantified	69.63 +/- 2.32 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	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 ] Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
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 ]
Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
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 ]
Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ] 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 ]
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 ]
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 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ] 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.

Associated OMIM IDs

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
231680 (Glutaric aciduria II)
266600 (Crohn's disease)
114500 (Colorectal cancer)
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022246

KNApSAcK ID

Not Available

Chemspider ID

10128115

KEGG Compound ID

C02838

BioCyc ID

L-OCTANOYLCARNITINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953814

PDB ID

Not Available

ChEBI ID

18102

Food Biomarker Ontology

Not Available

VMH ID

C8CRN

MarkerDB ID

MDB00000253

Good Scents ID

Not Available

References

Synthesis Reference

Duhr, Edward F.; Mauro, J. Matthew; Clennan, Edward L.; Barden, Roland E. The synthesis and biological activity of thiolcarnitine and its thiolesters. Lipids (1983), 18(5), 382-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Chace DH, DiPerna JC, Adam BW, Hannon WH: Errors caused by the use of D,L-octanoylcarnitine for blood-spot calibrators. Clin Chem. 2001 Apr;47(4):758-60. [PubMed:11274033 ]
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 ]

Enzymes

Enzyme Details

1. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:: CROT
Uniprot ID:: Q9UKG9
Molecular weight:: 10213.63

Reactions

Octanoyl-CoA + L-Carnitine → Coenzyme A + Octanoylcarnitine	details

Showing metabocard for Octanoylcarnitine (HMDB0000791)

MOL for HMDB0000791 (Octanoylcarnitine)

3D MOL for HMDB0000791 (Octanoylcarnitine)

3D SDF for HMDB0000791 (Octanoylcarnitine)

3D-SDF for HMDB0000791 (Octanoylcarnitine)

PDB for HMDB0000791 (Octanoylcarnitine)

3D PDB for HMDB0000791 (Octanoylcarnitine)

SMILES for HMDB0000791 (Octanoylcarnitine)

INCHI for HMDB0000791 (Octanoylcarnitine)

Structure for HMDB0000791 (Octanoylcarnitine)

3D Structure for HMDB0000791 (Octanoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions