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Showing metabocard for 6-Keto-decanoylcarnitine (HMDB0013202)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-11-30 15:50:53 UTC
Update Date2022-10-24 19:44:12 UTC
HMDB IDHMDB0013202
Secondary Accession Numbers
  • HMDB13202
Metabolite Identification
Common Name6-Keto-decanoylcarnitine
Description6-Keto-decanoylcarnitine is an acylcarnitine. More specifically, it is an 6-oxodecanoic 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. 6-Keto-decanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine 6-keto-decanoylcarnitine 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
Data?1582753100
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013202 (6-Keto-decanoylcarnitine)


  Mrv0541 02251208182D          

 23 22  0  0  0  0            999 V2000
   11.2120   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9264   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6409   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3554   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0699   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7844   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4988   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3567   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -8.6991    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7857   -7.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -6.6366    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7528   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1028   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -5.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4975   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3555   -7.8740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  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
 11  9  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
 12 11  1  0  0  0  0
 14 16  2  0  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22  1  1  0  0  0  0
 23  4  2  0  0  0  0
M  CHG  2  15  -1  18   1
M  END
Download

3D MOL for HMDB0013202 (6-Keto-decanoylcarnitine)

HMDB0013202
     RDKit          3D
6-Keto-decanoylcarnitine
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.8608   -1.3899    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1963   -0.7431   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.4196    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1184    0.2270   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.5698   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797    1.0947   -1.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.3028    0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    0.7356    0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.4242    1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.8215    1.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    0.1429    0.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3689   -1.1221    0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    0.7792    0.0184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    0.1799   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.4120   -2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -0.0797   -2.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671    0.6509   -2.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.3841   -3.2323 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.6049    0.4442   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1155    0.0015    0.6139 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.9063   -1.3923    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5697    0.2247    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6050    0.8170    1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6314   -2.4882    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9605   -1.2500    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.9184    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2290   -1.5045   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7413    0.1331   -0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6534    0.2089    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -1.3736    0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6464    1.1851   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244   -0.4607   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613   -0.8160    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    0.8117    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    0.1413   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454    1.8037    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147    1.0027    2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -0.6384    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470    1.9297    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    0.4797    2.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123   -0.9397   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106   -0.1693   -2.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    1.4741   -2.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8490    1.5334   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1775   -0.0547   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8096   -1.7957    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011   -1.9421   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450   -1.6129    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9479    0.1468    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7007    1.2156    0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9954   -0.5933   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9266    0.2292    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606    1.6771    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    1.2884    2.2925 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
M  CHG  2  18  -1  20   1
M  END
Download

3D SDF for HMDB0013202 (6-Keto-decanoylcarnitine)


  Mrv0541 02251208182D          

 23 22  0  0  0  0            999 V2000
   11.2120   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9264   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6409   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3554   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0699   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7844   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4988   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3567   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -8.6991    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7857   -7.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -6.6366    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7528   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1028   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -5.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4975   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3555   -7.8740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  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
 11  9  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
 12 11  1  0  0  0  0
 14 16  2  0  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22  1  1  0  0  0  0
 23  4  2  0  0  0  0
M  CHG  2  15  -1  18   1
M  END
> <DATABASE_ID>
HMDB0013202

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H31NO5/c1-5-6-9-14(19)10-7-8-11-17(22)23-15(12-16(20)21)13-18(2,3)4/h15H,5-13H2,1-4H3

> <INCHI_KEY>
DZALQUYFNHIYDL-UHFFFAOYSA-N

> <FORMULA>
C17H31NO5

> <MOLECULAR_WEIGHT>
329.4317

> <EXACT_MASS>
329.220223107

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.264225744502035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(6-oxodecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.21

> <JCHEM_LOGP>
-1.813081861138413

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2581348191021435

> <JCHEM_PKA_STRONGEST_BASIC>
-6.877320304991479

> <JCHEM_POLAR_SURFACE_AREA>
83.5

> <JCHEM_REFRACTIVITY>
110.11209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(6-oxodecanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0013202 (6-Keto-decanoylcarnitine)

HMDB0013202
     RDKit          3D
6-Keto-decanoylcarnitine
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.8608   -1.3899    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1963   -0.7431   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.4196    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1184    0.2270   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.5698   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797    1.0947   -1.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.3028    0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    0.7356    0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.4242    1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.8215    1.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    0.1429    0.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3689   -1.1221    0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    0.7792    0.0184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    0.1799   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.4120   -2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -0.0797   -2.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671    0.6509   -2.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.3841   -3.2323 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.6049    0.4442   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1155    0.0015    0.6139 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.9063   -1.3923    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5697    0.2247    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6050    0.8170    1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6314   -2.4882    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9605   -1.2500    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.9184    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2290   -1.5045   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7413    0.1331   -0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6534    0.2089    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -1.3736    0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6464    1.1851   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244   -0.4607   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613   -0.8160    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    0.8117    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    0.1413   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454    1.8037    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147    1.0027    2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -0.6384    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470    1.9297    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    0.4797    2.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123   -0.9397   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106   -0.1693   -2.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    1.4741   -2.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8490    1.5334   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1775   -0.0547   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8096   -1.7957    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011   -1.9421   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450   -1.6129    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9479    0.1468    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7007    1.2156    0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9954   -0.5933   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9266    0.2292    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606    1.6771    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    1.2884    2.2925 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
M  CHG  2  18  -1  20   1
M  END
Download

PDB for HMDB0013202 (6-Keto-decanoylcarnitine)

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.929 -17.008   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.263 -16.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.596 -17.008   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.930 -16.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.264 -17.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.598 -16.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.931 -17.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.265 -16.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.599 -17.008   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.599 -18.548   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      32.932 -16.238   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.932 -14.698   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.266 -13.928   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.600 -14.698   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      35.600 -16.238   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      36.933 -13.928   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      31.599 -13.928   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      31.599 -12.388   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0      33.139 -12.388   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.059 -12.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.599 -10.848   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.595 -16.238   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      24.930 -14.698   0.000  0.00  0.00           O+0
CONECT    1    2   22                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   13   11   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    1                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END
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3D PDB for HMDB0013202 (6-Keto-decanoylcarnitine)

COMPND    HMDB0013202
HETATM    1  C1  UNL     1       7.861  -1.390   1.012  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.196  -0.743  -0.184  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.750  -0.420   0.112  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.118   0.227  -1.104  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.693   0.570  -0.882  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.080   1.095  -1.791  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.993   0.303   0.384  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.543   0.736   0.347  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.950   0.424   1.711  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.489   0.821   1.822  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.393   0.143   0.876  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.369  -1.122   0.833  1.00  0.00           O  
HETATM   13  O3  UNL     1      -2.275   0.779   0.018  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.146   0.180  -0.879  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.831   0.412  -2.339  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.514  -0.080  -2.752  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.467   0.651  -2.698  1.00  0.00           O  
HETATM   18  O5  UNL     1      -1.294  -1.384  -3.232  1.00  0.00           O1-
HETATM   19  C14 UNL     1      -4.605   0.444  -0.651  1.00  0.00           C  
HETATM   20  N1  UNL     1      -5.116   0.001   0.614  1.00  0.00           N1+
HETATM   21  C15 UNL     1      -4.906  -1.392   0.868  1.00  0.00           C  
HETATM   22  C16 UNL     1      -6.570   0.225   0.569  1.00  0.00           C  
HETATM   23  C17 UNL     1      -4.605   0.817   1.680  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.631  -2.488   0.981  1.00  0.00           H  
HETATM   25  H2  UNL     1       8.961  -1.250   0.907  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.486  -0.918   1.940  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.229  -1.504  -1.015  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.741   0.133  -0.568  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.653   0.209   1.013  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.223  -1.374   0.299  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.646   1.185  -1.364  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.224  -0.461  -1.982  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.961  -0.816   0.555  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.439   0.812   1.263  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.064   0.141  -0.463  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.445   1.804   0.102  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.515   1.003   2.461  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.024  -0.638   1.964  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.647   1.930   1.840  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.825   0.480   2.853  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.012  -0.940  -0.749  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.611  -0.169  -2.913  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.019   1.474  -2.619  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.849   1.533  -0.745  1.00  0.00           H  
HETATM   45  H22 UNL     1      -5.178  -0.055  -1.456  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.810  -1.796   1.374  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.801  -1.942  -0.092  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.045  -1.613   1.552  1.00  0.00           H  
HETATM   49  H26 UNL     1      -6.948   0.147   1.597  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.701   1.216   0.098  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.995  -0.593  -0.069  1.00  0.00           H  
HETATM   52  H29 UNL     1      -3.927   0.229   2.340  1.00  0.00           H  
HETATM   53  H30 UNL     1      -4.061   1.677   1.228  1.00  0.00           H  
HETATM   54  H31 UNL     1      -5.419   1.288   2.292  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6    6    7
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   19   41
CONECT   15   16   42   43
CONECT   16   17   17   18
CONECT   19   20   44   45
CONECT   20   21   22   23
CONECT   21   46   47   48
CONECT   22   49   50   51
CONECT   23   52   53   54
END
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SMILES for HMDB0013202 (6-Keto-decanoylcarnitine)

CCCCC(=O)CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
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INCHI for HMDB0013202 (6-Keto-decanoylcarnitine)

InChI=1S/C17H31NO5/c1-5-6-9-14(19)10-7-8-11-17(22)23-15(12-16(20)21)13-18(2,3)4/h15H,5-13H2,1-4H3
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View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC17H31NO5
Average Molecular Weight329.4317
Monoisotopic Molecular Weight329.220223107
IUPAC Name3-[(6-oxodecanoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name3-[(6-oxodecanoyl)oxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCC(=O)CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C17H31NO5/c1-5-6-9-14(19)10-7-8-11-17(22)23-15(12-16(20)21)13-18(2,3)4/h15H,5-13H2,1-4H3
InChI KeyDZALQUYFNHIYDL-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP-1.2ALOGPS
logP-1.8ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area83.5 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity110.11 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.62330932474
DeepCCS[M-H]-184.60330932474
DeepCCS[M-2H]-221.14730932474
DeepCCS[M+Na]+197.43830932474
AllCCS[M+H]+187.532859911
AllCCS[M+H-H2O]+185.132859911
AllCCS[M+NH4]+189.832859911
AllCCS[M+Na]+190.532859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-189.032859911
AllCCS[M+HCOO]-190.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.4.72 minutes32390414
Predicted by Siyang on May 30, 202212.0852 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.59 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid184.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1757.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid188.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid182.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid166.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid155.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid481.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid450.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)633.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1317.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid379.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1571.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid256.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid337.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate389.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA225.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water35.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Keto-decanoylcarnitineCCCCC(=O)CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2800.2Standard polar33892256
6-Keto-decanoylcarnitineCCCCC(=O)CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C1818.1Standard non polar33892256
6-Keto-decanoylcarnitineCCCCC(=O)CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2171.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Keto-decanoylcarnitine,1TMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2309.5Semi standard non polar33892256
6-Keto-decanoylcarnitine,1TMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2288.7Standard non polar33892256
6-Keto-decanoylcarnitine,1TMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2746.9Standard polar33892256
6-Keto-decanoylcarnitine,1TMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2320.1Semi standard non polar33892256
6-Keto-decanoylcarnitine,1TMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2293.3Standard non polar33892256
6-Keto-decanoylcarnitine,1TMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C2754.9Standard polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2546.8Semi standard non polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2481.5Standard non polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #1CCCCC(=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2793.0Standard polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2552.8Semi standard non polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2486.2Standard non polar33892256
6-Keto-decanoylcarnitine,1TBDMS,isomer #2CCCC=C(CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2802.6Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029329
KNApSAcK IDNot Available
Chemspider ID35032588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481699
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.