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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-17 09:53:39 UTC

Update Date

2022-10-24 19:44:12 UTC

HMDB ID

HMDB0013324

Secondary Accession Numbers

HMDB13324

Metabolite Identification

Common Name

2-Octenoylcarnitine

Description

2-Octenoylcarnitine is an acylcarnitine. More specifically, it is an 2-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. 2-Octenoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine 2-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

HMDB0013324
     RDKit          3D
2-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.7188   -0.0778    1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    0.1443    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587    0.4053    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393    0.6433   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885   -0.5189   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.3772   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.6899   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.7976   -1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731    1.8283   -1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.2355   -1.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.3008   -1.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9299   -1.3061   -2.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087   -2.6623   -2.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.8632   -1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247   -3.6716   -3.1934 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5821   -0.5369   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050    0.4242    0.6545 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3464    0.3908    1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.1140    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374    1.7742    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267    0.9001    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2571   -0.4716    1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -0.7844    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -0.7856    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089    0.9607    2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746   -0.4814   -0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7876    1.2784   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0478   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    1.4959    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972   -1.4540   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.6788    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.2162   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    1.5021   -1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9115    0.6851   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -1.2351   -2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.9291   -3.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155   -0.5140   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5254   -1.5748    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374    1.2778    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8023   -0.5197    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179    0.3800    2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    1.0318    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -0.7291    2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5513   -0.2156    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    2.4318    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092    2.1346   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    1.8019   -0.1657 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
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 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
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  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  6
 12 35  1  0
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 16 37  1  0
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 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


  Mrv1652307191923522D          

 20 19  0  0  1  0            999 V2000
    8.8397   -4.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8358   -5.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5570   -4.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1259   -4.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5491   -6.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5577   -3.6042    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.4123   -4.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2668   -5.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5491   -6.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4085   -5.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6989   -4.4164    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9803   -6.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6939   -5.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4073   -6.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1211   -5.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8307   -6.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5444   -5.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2726   -3.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8435   -3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5577   -2.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 20  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0013324

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C\C(=O)O[C@@H](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+/t13-/m0/s1

> <INCHI_KEY>
LOSHAHDSFZXVCT-LXKVQUBZSA-N

> <FORMULA>
C15H27NO4

> <MOLECULAR_WEIGHT>
285.384

> <EXACT_MASS>
285.194008353

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
32.44575232314938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-1.2918446428050785

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.171784931901458

> <JCHEM_PKA_STRONGEST_BASIC>
-6.812938595497929

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
101.362

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013324
     RDKit          3D
2-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.7188   -0.0778    1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    0.1443    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587    0.4053    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393    0.6433   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885   -0.5189   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.3772   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.6899   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.7976   -1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731    1.8283   -1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.2355   -1.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.3008   -1.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9299   -1.3061   -2.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087   -2.6623   -2.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.8632   -1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247   -3.6716   -3.1934 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5821   -0.5369   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050    0.4242    0.6545 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3464    0.3908    1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.1140    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374    1.7742    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267    0.9001    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2571   -0.4716    1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -0.7844    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -0.7856    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089    0.9607    2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746   -0.4814   -0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7876    1.2784   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0478   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    1.4959    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972   -1.4540   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.6788    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.2162   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    1.5021   -1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9115    0.6851   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -1.2351   -2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.9291   -3.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155   -0.5140   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5254   -1.5748    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374    1.2778    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8023   -0.5197    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179    0.3800    2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    1.0318    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -0.7291    2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5513   -0.2156    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    2.4318    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092    2.1346   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    1.8019   -0.1657 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  6
 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                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0      16.501  -9.030   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.493 -10.565   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      17.840  -8.262   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.168  -8.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.825 -11.338   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      17.841  -6.728   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      13.836  -9.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.165 -10.577   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.825 -12.879   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.829 -10.559   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      12.505  -8.244   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      20.497 -11.351   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.829 -10.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.160 -11.356   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.493 -10.595   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.817 -11.369   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.150 -10.607   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.176  -5.959   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.508  -5.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.841  -5.187   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3   18   19   20                                             
CONECT    7    4   10   11                                                  
CONECT    8    5   12                                                       
CONECT    9    5                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    6                                                            
CONECT   19    6                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0013324
HETATM    1  C1  UNL     1       6.719  -0.078   1.971  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.272   0.144   1.555  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.159   0.405   0.082  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.739   0.643  -0.350  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.888  -0.519  -0.059  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.472  -0.377  -0.467  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.961   0.690  -1.050  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.433   0.798  -1.438  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.873   1.828  -1.988  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.285  -0.236  -1.204  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.632  -0.301  -1.506  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.930  -1.306  -2.628  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.509  -2.662  -2.266  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.976  -2.863  -1.151  1.00  0.00           O  
HETATM   15  O4  UNL     1      -2.725  -3.672  -3.193  1.00  0.00           O1-
HETATM   16  C12 UNL     1      -3.582  -0.537  -0.396  1.00  0.00           C  
HETATM   17  N1  UNL     1      -3.605   0.424   0.655  1.00  0.00           N1+
HETATM   18  C13 UNL     1      -2.346   0.391   1.370  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.701   0.114   1.592  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.837   1.774   0.226  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.127   0.900   2.277  1.00  0.00           H  
HETATM   22  H2  UNL     1       7.257  -0.472   1.086  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.705  -0.784   2.809  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.683  -0.786   1.791  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.809   0.961   2.120  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.575  -0.481  -0.454  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.788   1.278  -0.203  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.663   1.048  -1.376  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.373   1.496   0.300  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.297  -1.454  -0.479  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.838  -0.679   1.059  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.823  -1.216  -0.267  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.682   1.502  -1.222  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.911   0.685  -1.985  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.025  -1.235  -2.798  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.447  -0.929  -3.563  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.616  -0.514  -0.862  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.525  -1.575   0.026  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.737   1.278   1.097  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.802  -0.520   1.053  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.518   0.380   2.470  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.902   1.032   2.174  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.400  -0.729   2.263  1.00  0.00           H  
HETATM   44  H24 UNL     1      -5.551  -0.216   0.971  1.00  0.00           H  
HETATM   45  H25 UNL     1      -3.853   2.432   1.118  1.00  0.00           H  
HETATM   46  H26 UNL     1      -3.209   2.135  -0.584  1.00  0.00           H  
HETATM   47  H27 UNL     1      -4.898   1.802  -0.166  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

HMDB0013324
     RDKit          3D
2-Octenoylcarnitine
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.7188   -0.0778    1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    0.1443    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587    0.4053    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393    0.6433   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885   -0.5189   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.3772   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.6899   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.7976   -1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731    1.8283   -1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.2355   -1.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.3008   -1.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9299   -1.3061   -2.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087   -2.6623   -2.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.8632   -1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247   -3.6716   -3.1934 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5821   -0.5369   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050    0.4242    0.6545 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3464    0.3908    1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.1140    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374    1.7742    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267    0.9001    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2571   -0.4716    1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -0.7844    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -0.7856    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089    0.9607    2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746   -0.4814   -0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7876    1.2784   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0478   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    1.4959    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972   -1.4540   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.6788    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.2162   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    1.5021   -1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9115    0.6851   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -1.2351   -2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.9291   -3.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155   -0.5140   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5254   -1.5748    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374    1.2778    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8023   -0.5197    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179    0.3800    2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    1.0318    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -0.7291    2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5513   -0.2156    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    2.4318    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092    2.1346   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    1.8019   -0.1657 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  6
 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 NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3S)-3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoate	ChEBI
(e)-2-Octenoyl-L-carnitine	ChEBI
(3S)-3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoic acid	Generator
2-Octenoylcarnitine	ChEBI

Chemical Formula

C₁₅H₂₇NO₄

Average Molecular Weight

285.384

Monoisotopic Molecular Weight

285.194008353

IUPAC Name

(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C(=O)O[C@@H](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+/t13-/m0/s1

InChI Key

LOSHAHDSFZXVCT-LXKVQUBZSA-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

octenoyl-L-carnitine (CHEBI:71012 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0013324)

Endogenous

Endogenous (HMDB: HMDB0013324)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00055 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.3	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-6.8	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	11	ChemAxon
Refractivity	101.36 m³·mol⁻¹	ChemAxon
Polarizability	32.45 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]+	188.904	30932474
DeepCCS	[M-H]-	184.884	30932474
DeepCCS	[M-2H]-	221.429	30932474
DeepCCS	[M+Na]+	197.719	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 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.	4.29 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7768 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	120.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1665.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	208.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	528.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	472.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	548.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1405.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	383.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1621.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	147.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Octenoylcarnitine	CCCCC\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	2473.3	Standard polar	33892256
2-Octenoylcarnitine	CCCCC\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1724.8	Standard non polar	33892256
2-Octenoylcarnitine	CCCCC\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1909.8	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 - 2-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Octenoylcarnitine 30V, Positive-QTOF	splash10-000i-9000000000-61e0c82ca3b6073334d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Octenoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-75cfe3a164eb48e96f8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Octenoylcarnitine 20V, Positive-QTOF	splash10-000i-9100000000-3644d489ad51e75cbb21	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Octenoylcarnitine 10V, Positive-QTOF	splash10-000i-2090000000-db1295662d24e7591bf3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octenoylcarnitine 10V, Positive-QTOF	splash10-000i-0090000000-94aa77aae2ced01ee4aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octenoylcarnitine 20V, Positive-QTOF	splash10-000i-9050000000-68dc93b2a9eb3746b2b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octenoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.2 +/- 0.15 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.50 (0.08-1.20) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.100 +/- 0.050 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.123 +/- 0.070 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details

Associated Disorders and Diseases

Disease References

Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.

Associated OMIM IDs

601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28533412

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70679121

PDB ID

Not Available

ChEBI ID

71012

Food Biomarker Ontology

Not Available

VMH ID

C81CRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 2-Octenoylcarnitine (HMDB0013324)

MOL for HMDB0013324 (2-Octenoylcarnitine)

3D MOL for HMDB0013324 (2-Octenoylcarnitine)

3D SDF for HMDB0013324 (2-Octenoylcarnitine)

3D-SDF for HMDB0013324 (2-Octenoylcarnitine)

PDB for HMDB0013324 (2-Octenoylcarnitine)

3D PDB for HMDB0013324 (2-Octenoylcarnitine)

SMILES for HMDB0013324 (2-Octenoylcarnitine)

INCHI for HMDB0013324 (2-Octenoylcarnitine)

Structure for HMDB0013324 (2-Octenoylcarnitine)

3D Structure for HMDB0013324 (2-Octenoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra