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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-02-24 01:43:07 UTC

Update Date

2022-10-24 19:44:15 UTC

HMDB ID

HMDB0240750

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2E)-Octenoylcarnitine

Description

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

Structure

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

HMDB0240750
     RDKit          3D
(2E)-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.3205    1.4046    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    0.4001   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    0.8210   -1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7466    0.9250   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.3861   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -0.1911    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.8863    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761   -0.6578    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615    0.1747    1.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -1.3058    0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -1.0699    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -2.3361    1.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -3.4450    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -3.4381   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -4.6368    0.8895 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8894   -0.5867    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    0.6760   -0.5687 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8243    0.9641   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.5761   -1.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    1.7906    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4048    1.5124    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550    1.0772    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9982    2.3923    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1228    0.3493   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9420   -0.5980    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571    1.7482   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    0.0062   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    1.6963    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    1.2091   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834   -1.1721   -0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0048   -0.7028    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5333    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522   -1.5943   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648   -0.2943    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -2.6139    2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1916   -2.2188    2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923   -1.2557   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -0.3641    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6550    0.3057   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229    0.8958   -2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1763    2.0158   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811    1.0511   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.4613   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    1.1628   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3981    2.3427    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    2.5682   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    1.6159    1.2588 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
  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
  7 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
M  CHG  2  15  -1  17   1
M  END


  Mrv1652302242102432D          

 22 21  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -0.1105    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.9533    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.9520    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
HMDB0240750

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCCC)=C(\[H])C(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H27NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h9-10,13H,5-8,11-12H2,1-4H3/b10-9+

> <INCHI_KEY>
LOSHAHDSFZXVCT-MDZDMXLPSA-N

> <FORMULA>
C15H27NO4

> <MOLECULAR_WEIGHT>
285.384

> <EXACT_MASS>
285.194008353

$$$$

HMDB0240750
     RDKit          3D
(2E)-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.3205    1.4046    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    0.4001   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    0.8210   -1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7466    0.9250   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.3861   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -0.1911    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.8863    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761   -0.6578    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615    0.1747    1.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -1.3058    0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -1.0699    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -2.3361    1.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -3.4450    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -3.4381   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -4.6368    0.8895 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8894   -0.5867    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    0.6760   -0.5687 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8243    0.9641   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.5761   -1.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    1.7906    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4048    1.5124    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550    1.0772    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9982    2.3923    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1228    0.3493   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9420   -0.5980    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571    1.7482   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    0.0062   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    1.6963    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    1.2091   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834   -1.1721   -0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0048   -0.7028    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5333    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522   -1.5943   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648   -0.2943    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -2.6139    2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1916   -2.2188    2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923   -1.2557   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -0.3641    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6550    0.3057   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229    0.8958   -2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1763    2.0158   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811    1.0511   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.4613   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    1.1628   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3981    2.3427    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    2.5682   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    1.6159    1.2588 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
  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
  7 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
M  CHG  2  15  -1  17   1
M  END

HEADER    PROTEIN                                 24-FEB-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-21         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.979  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.439  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.519  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.646   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.979   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.646   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.979   4.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      12.979  -0.206   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      12.979   5.954   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      14.313   3.644   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0       8.978   3.644   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.312   1.334   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       6.311   3.644   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       7.645  -0.206   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   15   22                                                  
CONECT   11   13   14                                                       
CONECT   12   13   16                                                       
CONECT   13   11   12   20                                                  
CONECT   14   11   17   18                                                  
CONECT   15   10   19   20                                                  
CONECT   16    2    3    4   12                                             
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   13   15                                                       
CONECT   21    9                                                            
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0240750
HETATM    1  C1  UNL     1       6.320   1.405   0.751  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.183   0.400  -0.382  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.097   0.821  -1.350  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.747   0.925  -0.702  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.292  -0.386  -0.119  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.952  -0.191   0.493  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.909  -0.886   0.057  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.376  -0.658   0.690  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.461   0.175   1.624  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.546  -1.306   0.331  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.801  -1.070   0.963  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.175  -2.336   1.670  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.256  -3.445   0.701  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.956  -3.438  -0.338  1.00  0.00           O  
HETATM   15  O4  UNL     1      -2.516  -4.637   0.890  1.00  0.00           O1-
HETATM   16  C12 UNL     1      -3.889  -0.587   0.096  1.00  0.00           C  
HETATM   17  N1  UNL     1      -3.619   0.676  -0.569  1.00  0.00           N1+
HETATM   18  C13 UNL     1      -4.824   0.964  -1.368  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.528   0.576  -1.511  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.432   1.791   0.297  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.405   1.512   0.997  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.755   1.077   1.622  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.998   2.392   0.347  1.00  0.00           H  
HETATM   24  H4  UNL     1       7.123   0.349  -0.968  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.942  -0.598   0.013  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.357   1.748  -1.879  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.022   0.006  -2.108  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.714   1.696   0.105  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.012   1.209  -1.488  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.283  -1.172  -0.912  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.005  -0.703   0.633  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.874   0.533   1.295  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.052  -1.594  -0.750  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.665  -0.294   1.779  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.426  -2.614   2.452  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.192  -2.219   2.122  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.292  -1.256  -0.655  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.765  -0.364   0.787  1.00  0.00           H  
HETATM   39  H19 UNL     1      -5.655   0.306  -1.122  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.623   0.896  -2.454  1.00  0.00           H  
HETATM   41  H21 UNL     1      -5.176   2.016  -1.209  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.781   1.051  -2.500  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.263  -0.461  -1.751  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.656   1.163  -1.149  1.00  0.00           H  
HETATM   45  H25 UNL     1      -4.398   2.343   0.503  1.00  0.00           H  
HETATM   46  H26 UNL     1      -2.803   2.568  -0.234  1.00  0.00           H  
HETATM   47  H27 UNL     1      -2.968   1.616   1.259  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    7   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   16   34
CONECT   12   13   35   36
CONECT   13   14   14   15
CONECT   16   17   37   38
CONECT   17   18   19   20
CONECT   18   39   40   41
CONECT   19   42   43   44
CONECT   20   45   46   47
END

HMDB0240750
     RDKit          3D
(2E)-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.3205    1.4046    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    0.4001   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    0.8210   -1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7466    0.9250   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.3861   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -0.1911    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.8863    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761   -0.6578    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615    0.1747    1.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -1.3058    0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -1.0699    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -2.3361    1.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -3.4450    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -3.4381   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -4.6368    0.8895 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8894   -0.5867    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    0.6760   -0.5687 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8243    0.9641   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.5761   -1.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    1.7906    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4048    1.5124    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550    1.0772    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9982    2.3923    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1228    0.3493   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9420   -0.5980    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571    1.7482   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    0.0062   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    1.6963    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    1.2091   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834   -1.1721   -0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0048   -0.7028    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5333    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522   -1.5943   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648   -0.2943    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -2.6139    2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1916   -2.2188    2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923   -1.2557   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -0.3641    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6550    0.3057   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229    0.8958   -2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1763    2.0158   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811    1.0511   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.4613   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    1.1628   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3981    2.3427    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    2.5682   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    1.6159    1.2588 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
  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
  7 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
M  CHG  2  15  -1  17   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoate	ChEBI
trans-2-Octenoylcarnitine	ChEBI
3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoic acid	Generator

Chemical Formula

C₁₅H₂₇NO₄

Average Molecular Weight

285.384

Monoisotopic Molecular Weight

285.194008353

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(\[H])C(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C15H27NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h9-10,13H,5-8,11-12H2,1-4H3/b10-9+

InChI Key

LOSHAHDSFZXVCT-MDZDMXLPSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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

carboxylic ester (CHEBI:73037 )
O-acylcarnitine (CHEBI:73037 )
ammonium betaine (CHEBI:73037 )

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Cell

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

cytoplasm (PMID: 35710135)
mitochondrion matrix (PMID: 35710135)

Organelle

peroxisome (PMID: 35710135)

Source

Endogenous

Endogenous (HMDB: HMDB0240750)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.88	30932474
DeepCCS	[M-H]-	171.065	30932474
DeepCCS	[M-2H]-	207.402	30932474
DeepCCS	[M+Na]+	183.695	30932474
AllCCS	[M+H]+	175.1	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	179.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E)-Octenoylcarnitine	[H]\C(CCCCC)=C(\[H])C(=O)OC(CC([O-])=O)C[N+](C)(C)C	2412.9	Standard polar	33892256
(2E)-Octenoylcarnitine	[H]\C(CCCCC)=C(\[H])C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1608.4	Standard non polar	33892256
(2E)-Octenoylcarnitine	[H]\C(CCCCC)=C(\[H])C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1820.9	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 - (2E)-Octenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoylcarnitine 10V, Positive-QTOF	splash10-000i-0090000000-94aa77aae2ced01ee4aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoylcarnitine 20V, Positive-QTOF	splash10-000i-9050000000-68dc93b2a9eb3746b2b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21403177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464472

PDB ID

Not Available

ChEBI ID

73037

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for (2E)-Octenoylcarnitine (HMDB0240750)

MOL for HMDB0240750 ((2E)-Octenoylcarnitine)

3D MOL for HMDB0240750 ((2E)-Octenoylcarnitine)

3D SDF for HMDB0240750 ((2E)-Octenoylcarnitine)

3D-SDF for HMDB0240750 ((2E)-Octenoylcarnitine)

PDB for HMDB0240750 ((2E)-Octenoylcarnitine)

3D PDB for HMDB0240750 ((2E)-Octenoylcarnitine)

SMILES for HMDB0240750 ((2E)-Octenoylcarnitine)

INCHI for HMDB0240750 ((2E)-Octenoylcarnitine)

Structure for HMDB0240750 ((2E)-Octenoylcarnitine)

3D Structure for HMDB0240750 ((2E)-Octenoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra