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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-22 10:23:05 UTC

Update Date

2023-05-30 20:55:49 UTC

HMDB ID

HMDB0013326

Secondary Accession Numbers

HMDB13326

Metabolite Identification

Common Name

trans-2-Dodecenoylcarnitine

Description

trans-2-Dodecenoylcarnitine is an acylcarnitine. More specifically, it is an trans-2-dodecenoic 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. trans-2-Dodecenoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine trans-2-dodecenoylcarnitine 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. In particular trans-2-dodecenoylcarnitine is elevated in the blood or plasma of individuals with mitochondrial dysfunction in diabetes patients (PMID: 28726959 ) and children obesity (PMID: 23108202 ). It is also decreased in the blood or plasma of individuals with placental abruption (PMID: 27300725 ) increase in dodecanoylcarnitine/dodecenoylcarnitine (c12 / c12:1). 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

HMDB0013326
     RDKit          3D
trans-2-Dodecenoylcarnitine
 59 58  0  0  0  0  0  0  0  0999 V2000
    6.6881    2.4905    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138    1.0344    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.1600   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.3511   -1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.0246   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -1.3893    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.7069    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -1.5231    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -2.4202   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -2.2893   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870   -1.4616   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -1.3159   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742   -1.9295   -1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -0.4502   -0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.2010   -0.6802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4015   -0.5104    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.1861    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6009   -0.3055    2.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7625    0.0585    2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4677   -1.1876    3.3995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.3502    1.1331   -1.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8942    2.1522   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860    1.0883   -2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    1.4309   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    2.6786   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823    3.0494    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484    2.8685    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8293    0.8634    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    0.7855    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728   -0.9039   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2717    0.4855   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.3367   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0462    1.3728   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027    0.6854    0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2236   -0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1120   -2.1157   -0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1144   -1.5169    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.7366    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247   -1.0115    2.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -0.4562    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.8392    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -2.1402   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -3.4613    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -2.8960   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.8879    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4688   -0.8750   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4488   -1.5932    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.2497   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5290    1.2834    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410   -0.0037    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.8018   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    1.7265    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6856    2.8848   -0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    2.0928   -2.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    0.9010   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.2783   -3.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    2.2622   -2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0346    0.5649   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3509    1.7958   -1.0760 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 15 46  1  6
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
M  CHG  2  20  -1  21   1
M  END


  Mrv1652307191923522D          

 24 23  0  0  0  0            999 V2000
   14.3066   -3.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0211   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5922   -3.1591    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.8777   -2.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1796   -3.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0047   -2.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3066   -4.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1632   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8777   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5922   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5922   -5.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4487   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7342   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0197   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3051   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5907   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7356   -3.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4501   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4501   -2.3341    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.1646   -3.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8763   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4473   -4.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7328   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  1  7  1  6  0  0  0
  8  9  2  0  0  0  0
 10  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  2  1  0  0  0  0
 19 18  1  0  0  0  0
 18 20  2  0  0  0  0
 17 18  1  0  0  0  0
 21 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
M  CHG  2   3   1  19  -1
M  END
> <DATABASE_ID>
HMDB0013326

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H35NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(20(2,3)4)15-16-18(21)22/h13-14,17H,5-12,15-16H2,1-4H3/b14-13+/t17-/m0/s1

> <INCHI_KEY>
JEOZLTJHDSKQIT-CLVCIHKQSA-N

> <FORMULA>
C19H35NO4

> <MOLECULAR_WEIGHT>
341.492

> <EXACT_MASS>
341.256608611

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.07645331873611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
0.812500756528254

> <ALOGPS_LOGS>
-7.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.126756519266556

> <JCHEM_PKA_STRONGEST_BASIC>
-6.922925627504369

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
119.69879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013326
     RDKit          3D
trans-2-Dodecenoylcarnitine
 59 58  0  0  0  0  0  0  0  0999 V2000
    6.6881    2.4905    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138    1.0344    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.1600   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.3511   -1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.0246   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -1.3893    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.7069    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -1.5231    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -2.4202   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -2.2893   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870   -1.4616   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -1.3159   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742   -1.9295   -1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -0.4502   -0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.2010   -0.6802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4015   -0.5104    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.1861    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6009   -0.3055    2.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7625    0.0585    2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4677   -1.1876    3.3995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.3502    1.1331   -1.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8942    2.1522   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860    1.0883   -2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    1.4309   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    2.6786   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823    3.0494    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484    2.8685    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8293    0.8634    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    0.7855    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728   -0.9039   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2717    0.4855   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.3367   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0462    1.3728   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027    0.6854    0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2236   -0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1120   -2.1157   -0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1144   -1.5169    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.7366    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247   -1.0115    2.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -0.4562    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.8392    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -2.1402   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -3.4613    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -2.8960   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.8879    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4688   -0.8750   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4488   -1.5932    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.2497   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5290    1.2834    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410   -0.0037    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.8018   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    1.7265    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6856    2.8848   -0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    2.0928   -2.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    0.9010   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.2783   -3.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    2.2622   -2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0346    0.5649   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3509    1.7958   -1.0760 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 15 46  1  6
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
M  CHG  2  20  -1  21   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      26.706  -6.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.039  -5.897   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      25.372  -5.897   0.000  0.00  0.00           N+1
HETATM    4  C   UNK     0      24.038  -5.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.602  -7.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.142  -4.563   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.706  -8.207   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.705  -8.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.038  -8.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.372  -8.977   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      25.372 -10.517   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.371  -8.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.037  -8.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.703  -8.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.370  -8.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.036  -8.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.373  -6.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.707  -5.897   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      30.707  -4.357   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      32.041  -6.667   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.702  -8.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.369  -8.207   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.035  -8.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.701  -8.207   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1   17                                                       
CONECT    3    1    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1   10                                                       
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9    7   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   21                                                       
CONECT   17    2   18                                                       
CONECT   18   19   20   17                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0013326
HETATM    1  C1  UNL     1       6.688   2.490   0.393  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.814   1.034   0.704  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.545   0.160  -0.504  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.174   0.351  -1.055  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.086   0.025  -0.056  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.142  -1.389   0.417  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.062  -1.707   1.407  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.666  -1.523   0.887  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.444  -2.420  -0.304  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.084  -2.289  -0.865  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.787  -1.462  -0.330  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.128  -1.316  -0.865  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.574  -1.930  -1.840  1.00  0.00           O  
HETATM   14  O2  UNL     1      -3.010  -0.450  -0.289  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.313  -0.201  -0.680  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.401  -0.510   0.262  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.395   0.186   1.568  1.00  0.00           C  
HETATM   18  C16 UNL     1      -6.601  -0.306   2.334  1.00  0.00           C  
HETATM   19  O3  UNL     1      -7.763   0.059   2.043  1.00  0.00           O  
HETATM   20  O4  UNL     1      -6.468  -1.188   3.400  1.00  0.00           O1-
HETATM   21  N1  UNL     1      -4.350   1.133  -1.251  1.00  0.00           N1+
HETATM   22  C17 UNL     1      -3.894   2.152  -0.361  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.386   1.088  -2.368  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.631   1.431  -1.859  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.144   2.679  -0.596  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.282   3.049   1.144  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.648   2.868   0.470  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.829   0.863   1.114  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.109   0.786   1.538  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.773  -0.904  -0.302  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.272   0.486  -1.284  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.022  -0.337  -1.914  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.046   1.373  -1.451  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.203   0.685   0.817  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.079   0.224  -0.468  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.112  -2.116  -0.440  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.114  -1.517   0.976  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.212  -2.737   1.794  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.225  -1.012   2.280  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.516  -0.456   0.639  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.988  -1.839   1.735  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.179  -2.140  -1.085  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.675  -3.461   0.023  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.156  -2.896  -1.721  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.474  -0.888   0.526  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.469  -0.875  -1.582  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.449  -1.593   0.430  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.368  -0.250  -0.241  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.529   1.283   1.511  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.541  -0.004   2.217  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.091   2.802  -0.822  1.00  0.00           H  
HETATM   52  H28 UNL     1      -3.378   1.726   0.550  1.00  0.00           H  
HETATM   53  H29 UNL     1      -4.686   2.885  -0.062  1.00  0.00           H  
HETATM   54  H30 UNL     1      -3.348   2.093  -2.840  1.00  0.00           H  
HETATM   55  H31 UNL     1      -2.363   0.901  -1.953  1.00  0.00           H  
HETATM   56  H32 UNL     1      -3.638   0.278  -3.079  1.00  0.00           H  
HETATM   57  H33 UNL     1      -5.560   2.262  -2.592  1.00  0.00           H  
HETATM   58  H34 UNL     1      -6.035   0.565  -2.423  1.00  0.00           H  
HETATM   59  H35 UNL     1      -6.351   1.796  -1.076  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   42   43
CONECT   10   11   11   44
CONECT   11   12   45
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   21   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   19   20
CONECT   21   22   23   24
CONECT   22   51   52   53
CONECT   23   54   55   56
CONECT   24   57   58   59
END

HMDB0013326
     RDKit          3D
trans-2-Dodecenoylcarnitine
 59 58  0  0  0  0  0  0  0  0999 V2000
    6.6881    2.4905    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138    1.0344    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.1600   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.3511   -1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.0246   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -1.3893    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.7069    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -1.5231    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -2.4202   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -2.2893   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870   -1.4616   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -1.3159   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742   -1.9295   -1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -0.4502   -0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.2010   -0.6802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4015   -0.5104    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.1861    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6009   -0.3055    2.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7625    0.0585    2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4677   -1.1876    3.3995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.3502    1.1331   -1.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8942    2.1522   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860    1.0883   -2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    1.4309   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    2.6786   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823    3.0494    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484    2.8685    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8293    0.8634    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    0.7855    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728   -0.9039   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2717    0.4855   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.3367   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0462    1.3728   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027    0.6854    0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2236   -0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1120   -2.1157   -0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1144   -1.5169    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.7366    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247   -1.0115    2.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -0.4562    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.8392    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -2.1402   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -3.4613    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -2.8960   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.8879    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4688   -0.8750   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4488   -1.5932    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.2497   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5290    1.2834    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410   -0.0037    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.8018   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    1.7265    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6856    2.8848   -0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    2.0928   -2.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    0.9010   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.2783   -3.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    2.2622   -2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0346    0.5649   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3509    1.7958   -1.0760 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 15 46  1  6
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
M  CHG  2  20  -1  21   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4S)-4-[(2E)-Dodec-2-enoyloxy]-4-(trimethylazaniumyl)butanoic acid	Generator

Chemical Formula

C₁₉H₃₅NO₄

Average Molecular Weight

341.492

Monoisotopic Molecular Weight

341.256608611

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C

InChI Identifier

InChI=1S/C19H35NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(20(2,3)4)15-16-18(21)22/h13-14,17H,5-12,15-16H2,1-4H3/b14-13+/t17-/m0/s1

InChI Key

JEOZLTJHDSKQIT-CLVCIHKQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26010610)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0013326)

Food

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)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Endogenous

Endogenous (HMDB: HMDB0013326)

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	3.4e-05 g/L	ALOGPS
logP	0.16	ALOGPS
logP	0.81	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-6.9	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	15	ChemAxon
Refractivity	119.7 m³·mol⁻¹	ChemAxon
Polarizability	41.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	199.275	30932474
DeepCCS	[M-H]-	195.255	30932474
DeepCCS	[M-2H]-	231.798	30932474
DeepCCS	[M+Na]+	208.09	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-2-Dodecenoylcarnitine	CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C	2939.7	Standard polar	33892256
trans-2-Dodecenoylcarnitine	CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C	2155.4	Standard non polar	33892256
trans-2-Dodecenoylcarnitine	CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C	2339.5	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 - trans-2-Dodecenoylcarnitine 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 - trans-2-Dodecenoylcarnitine 10V, Positive-QTOF	splash10-006y-1449000000-4d5f18101fd4b462d78f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 20V, Positive-QTOF	splash10-0f76-2900000000-6152f4520fea29ca59ee	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 40V, Positive-QTOF	splash10-052o-9400000000-5532b23cc830002dfa1b	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 10V, Negative-QTOF	splash10-002f-0519000000-ea501ed93964249ff1a1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 20V, Negative-QTOF	splash10-0059-0931000000-956fd9059c7c922eb157	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 40V, Negative-QTOF	splash10-0fbd-4900000000-c91b256ba56f3f8abb22	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 10V, Negative-QTOF	splash10-0006-0109000000-84c2bbe51f86a7920105	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 20V, Negative-QTOF	splash10-052f-7908000000-c995a6ea71c70fec6422	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 40V, Negative-QTOF	splash10-0002-2900000000-9e36dd4310c6e7bc28d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 10V, Positive-QTOF	splash10-0006-1409000000-0fd67cda7ed388b00a7d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 20V, Positive-QTOF	splash10-03du-9722000000-efa5d1910215d7a243d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Dodecenoylcarnitine 40V, Positive-QTOF	splash10-01p9-9200000000-f04e78776ab96e5e593a	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.10-0.40 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.23(0.07) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.10 +/- 0.03 uM	Children (1-13 years old)	Both	Normal	23108202	details
Blood	Detected and Quantified	<0.12 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Feces	Detected and Quantified	0.47 +/- 0.33 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.43 +/- 0.26 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.028 (0.011-0.042) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.06 (0.02-0.08) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.02-0.14 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.06 +/- 0.02 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.06 +/- 0.02 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.29(0.1) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.16 +/- 0.05 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.16 +/- 0.06 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.16 +/- 0.06 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.16 +/- 0.07 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.130 +/- 0.040 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.131 +/- 0.046 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.13 +/- 0.04 uM	Children (1-13 years old)	Both	Obese	23108202	details
Blood	Detected and Quantified	0.15 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.22 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details

Associated Disorders and Diseases

Disease References

Glutaric aciduria II
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Obesity
Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ] Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ] 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

231680 (Glutaric aciduria II)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30776709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481671

PDB ID

Not Available

ChEBI ID

89717

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000852

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 ]
Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
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 ]
Abu Bakar MH, Sarmidi MR: Association of cultured myotubes and fasting plasma metabolite profiles with mitochondrial dysfunction in type 2 diabetes subjects. Mol Biosyst. 2017 Aug 22;13(9):1838-1853. doi: 10.1039/c7mb00333a. [PubMed:28726959 ]
Gelaye B, Sumner SJ, McRitchie S, Carlson JE, Ananth CV, Enquobahrie DA, Qiu C, Sorensen TK, Williams MA: Maternal Early Pregnancy Serum Metabolomics Profile and Abnormal Vaginal Bleeding as Predictors of Placental Abruption: A Prospective Study. PLoS One. 2016 Jun 14;11(6):e0156755. doi: 10.1371/journal.pone.0156755. eCollection 2016. [PubMed:27300725 ]
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 trans-2-Dodecenoylcarnitine (HMDB0013326)

MOL for HMDB0013326 (trans-2-Dodecenoylcarnitine)

3D MOL for HMDB0013326 (trans-2-Dodecenoylcarnitine)

3D SDF for HMDB0013326 (trans-2-Dodecenoylcarnitine)

3D-SDF for HMDB0013326 (trans-2-Dodecenoylcarnitine)

PDB for HMDB0013326 (trans-2-Dodecenoylcarnitine)

3D PDB for HMDB0013326 (trans-2-Dodecenoylcarnitine)

SMILES for HMDB0013326 (trans-2-Dodecenoylcarnitine)

INCHI for HMDB0013326 (trans-2-Dodecenoylcarnitine)

Structure for HMDB0013326 (trans-2-Dodecenoylcarnitine)

3D Structure for HMDB0013326 (trans-2-Dodecenoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra