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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:44 UTC

Update Date

2022-10-24 19:44:10 UTC

HMDB ID

HMDB0002250

Secondary Accession Numbers

HMDB0062713
HMDB02250
HMDB62713

Metabolite Identification

Common Name

Dodecanoylcarnitine

Description

Dodecanoylcarnitine is an acylcarnitine. More specifically, it is an dodecanoic 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. Dodecanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine Dodecanoylcarnitine 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 Dodecanoylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211 ), Yin deficiency (PMID: 31909891 ), multiple acyl coenzyme A dehydrogenase deficiency (PMID: 30510944 ), CVD in type 2 diabetes Mellitus (PMID: 32431666 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with Celiac disease (PMID: 16425363 ), psoriasis (PMID: 28695330 ), intracerebral hemorrhage (PMID: 29265114 ), and pregnancy (PMID: 24704061 - in serum of pregnant women with fetus with CHD). Dodecanoylcarnitine is elevated in the urine of individuals with renal cell carcinoma (PMID: 29658093 ). 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 ). Dodecanoylcarnitine is also present in fatty acid oxidation disorders such as long-chain acyl CoA dehydrogenase deficiency, carnitine palmitoyltransferase I deficiency, and carnitine palmitoyltransferase II deficiency (PMID: 12828998 ). 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

HMDB0002250
     RDKit          3D
Dodecanoylcarnitine
 62 61  0  0  0  0  0  0  0  0999 V2000
    7.9243   -1.8236    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716   -0.3273    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9837    0.0851   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5891   -0.5042   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -0.0328   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830   -0.5605   -1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -0.1188   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    1.3663   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.7362    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1898    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.6587    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712    1.1884    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    1.5279    2.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    0.4214    0.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458    0.0227    0.8735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8375   -1.4790    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376   -2.2278   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -2.5906   -1.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -2.5667   -0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6905    0.5369   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0915    0.2778   -0.1357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8032    1.3933   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6379    0.3359    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9039   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -2.2766    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339   -2.2489   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8824   -2.0290    1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7871    0.1086    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3391    0.0771    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4965   -0.2783   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8710    1.1877   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -0.1559    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -1.5920   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155    1.0673   -2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -0.4580   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411   -0.1831   -2.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -1.6582   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -0.5160   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.5624    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.7548   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.8408   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    2.8387    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844    1.3653    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.5990   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.0841    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    1.2161    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.7405    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687    0.4497    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504   -1.6424    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071   -1.8780    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6782   -3.5572   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602    0.1598   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    1.6584   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4289    2.3539   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8628    1.2737   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7232    1.2210   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6883    0.7736    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0953    0.9891    1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8297   -0.6981    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5980   -1.8059   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6428   -0.7479   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502   -1.0767   -1.7716 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  1  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  2  0
 17 19  1  0
 15 20  1  0
 20 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
 10 45  1  0
 11 46  1  0
 11 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
M  CHG  1  21   1
M  END

      
  Mrv1652303062019112D          

 24 23  0  0  0  0            999 V2000
 2496.0753 2499.7344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2496.7892 2499.3212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5033 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2172 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9313 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6453 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3595 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0735 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7876 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5037 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2178 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9317 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.6459 2499.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.3600 2499.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5033 2500.5588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0753 2500.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3611 2500.9701    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2494.6430 2500.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3611 2501.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2494.5079 2501.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3690 2499.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3690 2498.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0833 2498.0730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2494.6551 2498.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  6  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 15  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  CHG  2  17   1  23  -1
M  END
> <DATABASE_ID>
HMDB0002250

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1

> <INCHI_KEY>
FUJLYHJROOYKRA-QGZVFWFLSA-N

> <FORMULA>
C19H37NO4

> <MOLECULAR_WEIGHT>
343.5014

> <EXACT_MASS>
343.272258677

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.848080190302625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
0.25527319419491984

> <ALOGPS_LOGS>
-7.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022333

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
118.67269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lauroyl-L(-)-carnitin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002250
     RDKit          3D
Dodecanoylcarnitine
 62 61  0  0  0  0  0  0  0  0999 V2000
    7.9243   -1.8236    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716   -0.3273    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9837    0.0851   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5891   -0.5042   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -0.0328   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830   -0.5605   -1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -0.1188   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    1.3663   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.7362    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1898    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.6587    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712    1.1884    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    1.5279    2.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    0.4214    0.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458    0.0227    0.8735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8375   -1.4790    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376   -2.2278   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -2.5906   -1.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -2.5667   -0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6905    0.5369   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0915    0.2778   -0.1357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8032    1.3933   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6379    0.3359    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9039   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -2.2766    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339   -2.2489   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8824   -2.0290    1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7871    0.1086    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3391    0.0771    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4965   -0.2783   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8710    1.1877   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -0.1559    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -1.5920   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155    1.0673   -2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -0.4580   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411   -0.1831   -2.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -1.6582   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -0.5160   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.5624    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.7548   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.8408   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    2.8387    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844    1.3653    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.5990   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.0841    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    1.2161    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.7405    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687    0.4497    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504   -1.6424    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071   -1.8780    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6782   -3.5572   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602    0.1598   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    1.6584   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4289    2.3539   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8628    1.2737   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7232    1.2210   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6883    0.7736    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0953    0.9891    1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8297   -0.6981    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5980   -1.8059   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6428   -0.7479   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502   -1.0767   -1.7716 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  1  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  2  0
 17 19  1  0
 15 20  1  0
 20 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
 10 45  1  0
 11 46  1  0
 11 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
M  CHG  1  21   1
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    4659.3404666.171   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4660.6734665.400   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4662.0064666.171   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4663.3394665.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4664.6724666.171   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4666.0054665.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4667.3384666.171   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4668.6714665.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4670.0034666.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4671.3404665.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4672.6734666.171   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4674.0064665.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4675.3394666.171   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4676.6724665.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    4662.0064667.710   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    4659.3404667.710   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    4658.0074668.478   0.000  0.00  0.00           N+1
HETATM   18  C   UNK     0    4656.6674667.706   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4658.0074670.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4656.4154669.398   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4658.0224665.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4658.0224663.841   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    4659.3554663.070   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0    4656.6894663.070   0.000  0.00  0.00           O+0
CONECT    1    2   16   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    3                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002250
HETATM    1  C1  UNL     1       7.924  -1.824   0.679  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.772  -0.327   0.583  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.984   0.085  -0.642  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.589  -0.504  -0.631  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.893  -0.033  -1.888  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.483  -0.561  -1.989  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.627  -0.119  -0.825  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.511   1.366  -0.719  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.654   1.736   0.459  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.246   1.190   0.383  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.460   1.659   1.635  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.871   1.188   1.692  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.530   1.528   2.708  1.00  0.00           O  
HETATM   14  O2  UNL     1      -2.465   0.421   0.708  1.00  0.00           O  
HETATM   15  C13 UNL     1      -3.846   0.023   0.873  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.837  -1.479   1.066  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.238  -2.228  -0.042  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.890  -2.591  -1.033  1.00  0.00           O  
HETATM   19  O4  UNL     1      -1.882  -2.567  -0.022  1.00  0.00           O  
HETATM   20  C16 UNL     1      -4.690   0.537  -0.221  1.00  0.00           C  
HETATM   21  N1  UNL     1      -6.092   0.278  -0.136  1.00  0.00           N1+
HETATM   22  C17 UNL     1      -6.803   1.393  -0.842  1.00  0.00           C  
HETATM   23  C18 UNL     1      -6.638   0.336   1.209  1.00  0.00           C  
HETATM   24  C19 UNL     1      -6.566  -0.904  -0.783  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.126  -2.277   1.277  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.034  -2.249  -0.337  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.882  -2.029   1.207  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.787   0.109   0.483  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.339   0.077   1.511  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.496  -0.278  -1.553  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.871   1.188  -0.607  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.096  -0.156   0.287  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.676  -1.592  -0.657  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.916   1.067  -2.005  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.457  -0.458  -2.747  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.041  -0.183  -2.912  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.490  -1.658  -2.017  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.597  -0.516  -1.064  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.917  -0.562   0.128  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.543   1.755  -0.487  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.199   1.841  -1.648  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.551   2.839   0.578  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.084   1.365   1.411  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.275   1.599  -0.509  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.224   0.084   0.301  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.068   1.216   2.504  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.358   2.740   1.704  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.169   0.450   1.839  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.150  -1.642   1.958  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.807  -1.878   1.394  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.678  -3.557  -0.123  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.360   0.160  -1.231  1.00  0.00           H  
HETATM   53  H29 UNL     1      -4.554   1.658  -0.325  1.00  0.00           H  
HETATM   54  H30 UNL     1      -6.429   2.354  -0.489  1.00  0.00           H  
HETATM   55  H31 UNL     1      -7.863   1.274  -0.537  1.00  0.00           H  
HETATM   56  H32 UNL     1      -6.723   1.221  -1.920  1.00  0.00           H  
HETATM   57  H33 UNL     1      -7.688   0.774   1.181  1.00  0.00           H  
HETATM   58  H34 UNL     1      -6.095   0.989   1.895  1.00  0.00           H  
HETATM   59  H35 UNL     1      -6.830  -0.698   1.608  1.00  0.00           H  
HETATM   60  H36 UNL     1      -6.598  -1.806  -0.155  1.00  0.00           H  
HETATM   61  H37 UNL     1      -7.643  -0.748  -1.097  1.00  0.00           H  
HETATM   62  H38 UNL     1      -6.050  -1.077  -1.772  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   44   45
CONECT   11   12   46   47
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   20   48
CONECT   16   17   49   50
CONECT   17   18   18   19
CONECT   19   51
CONECT   20   21   52   53
CONECT   21   22   23   24
CONECT   22   54   55   56
CONECT   23   57   58   59
CONECT   24   60   61   62
END

HMDB0002250
     RDKit          3D
Dodecanoylcarnitine
 62 61  0  0  0  0  0  0  0  0999 V2000
    7.9243   -1.8236    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716   -0.3273    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9837    0.0851   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5891   -0.5042   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -0.0328   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830   -0.5605   -1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -0.1188   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    1.3663   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.7362    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1898    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.6587    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712    1.1884    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    1.5279    2.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    0.4214    0.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458    0.0227    0.8735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8375   -1.4790    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376   -2.2278   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -2.5906   -1.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -2.5667   -0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6905    0.5369   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0915    0.2778   -0.1357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8032    1.3933   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6379    0.3359    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9039   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -2.2766    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339   -2.2489   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8824   -2.0290    1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7871    0.1086    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3391    0.0771    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4965   -0.2783   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8710    1.1877   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -0.1559    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -1.5920   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155    1.0673   -2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -0.4580   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411   -0.1831   -2.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -1.6582   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -0.5160   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.5624    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.7548   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.8408   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    2.8387    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844    1.3653    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.5990   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.0841    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    1.2161    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.7405    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687    0.4497    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504   -1.6424    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071   -1.8780    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6782   -3.5572   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602    0.1598   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    1.6584   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4289    2.3539   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8628    1.2737   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7232    1.2210   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6883    0.7736    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0953    0.9891    1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8297   -0.6981    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5980   -1.8059   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6428   -0.7479   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502   -1.0767   -1.7716 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  1  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  2  0
 17 19  1  0
 15 20  1  0
 20 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
 10 45  1  0
 11 46  1  0
 11 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
M  CHG  1  21   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Lauroylcarnitine	ChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoate	ChEBI
(R)-Dodecanoylcarnitine	ChEBI
Dodecanoyl-L-carnitine	ChEBI
L-Carnitine dodecanoyl ester	ChEBI
Lauroyl-L(-)-carnitin	ChEBI
Lauroyl-L-carnitine	ChEBI
Lauroylcarnitine	ChEBI
Laurylcarnitine	ChEBI
O-C12:0-L-Carnitine	ChEBI
O-Dodecanoyl-R-carnitine	ChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acid	Generator
C12 Carnitine	HMDB
L-Lauroylcarnitine	HMDB
Lauroyl-L(-)-carnitine	HMDB
Dodecanoylcarnitine	HMDB
O-Dodecanoylcarnitine	ChEBI, HMDB
O-Lauroylcarnitine	ChEBI, HMDB
O-Lauroyl-L-carnitine	ChEBI, HMDB

Chemical Formula

C₁₉H₃₈NO₄

Average Molecular Weight

344.515

Monoisotopic Molecular Weight

344.279535128

IUPAC Name

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

Traditional Name

lauroyl-L(-)-carnitin

CAS Registry Number

25518-54-1

SMILES

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

InChI Identifier

InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/p+1/t17-/m1/s1

InChI Key

FUJLYHJROOYKRA-QGZVFWFLSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:77086 )
O-dodecanoylcarnitine (CHEBI:77086 )
laurate ester (CHEBI:77086 )

Ontology

Not Available

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	3.8e-05 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.26	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	118.67 m³·mol⁻¹	ChemAxon
Polarizability	41.85 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]+	197.583	30932474
DeepCCS	[M-H]-	193.666	30932474
DeepCCS	[M-2H]-	230.106	30932474
DeepCCS	[M+Na]+	206.398	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dodecanoylcarnitine	CCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3343.1	Standard polar	33892256
Dodecanoylcarnitine	CCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2135.5	Standard non polar	33892256
Dodecanoylcarnitine	CCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2380.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dodecanoylcarnitine,1TMS,isomer #1	CCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2405.1	Semi standard non polar	33892256
Dodecanoylcarnitine,1TBDMS,isomer #1	CCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	2636.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dodecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9300000000-0cd49618a50984aad982	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dodecanoylcarnitine 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 - Dodecanoylcarnitine , negative-QTOF	splash10-0002-0900000000-1c57ff1372236d823d80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dodecanoylcarnitine , positive-QTOF	splash10-000i-9000000000-ef35ea7a4d61bac8cb20	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dodecanoylcarnitine 10V, Positive-QTOF	splash10-0006-0009000000-ce07549e40447c69729f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dodecanoylcarnitine 20V, Positive-QTOF	splash10-000l-9005000000-ce18984499544d19b739	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dodecanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Liver
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.1 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.057-0.190 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.052 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.057-0.190 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.1(0.04) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	0.038 (0.005-0.069) uM	Children (1-13 years old)	Both	Normal	9034211	details
Feces	Detected and Quantified	0.42 +/- 0.28 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.64 +/- 0.3 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.02 (0.01-0.04) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.03-0.25 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.07(0.03-0.14) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.07(0.04-0.28) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.032 +/- 0.002 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details
Blood	Detected and Quantified	0.15(0.07) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.045 (0.0197) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.0651 (0.0228) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.080 +/- 0.025 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.086 +/- 0.038 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.124 (0.090-0.162) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details

Associated Disorders and Diseases

Disease References

Celiac disease
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
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

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022928

KNApSAcK ID

C00052268

Chemspider ID

147288

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6573

PubChem Compound

168381

PDB ID

Not Available

ChEBI ID

77086

Food Biomarker Ontology

Not Available

VMH ID

DDECCRN

MarkerDB ID

MDB00000387

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 ]
Moder M, Kiessling A, Loster H, Bruggemann L: The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: a new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem. 2003 Jan;375(2):200-10. Epub 2003 Jan 4. [PubMed:12560963 ]
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72. [PubMed:12828998 ]
Morrow RJ, Rose ME: Isolation of acylcarnitines from urine: a comparison of methods and application to long-chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 1992 Oct 15;211(1-2):73-81. [PubMed:1468155 ]
Vianey-Saban C, Divry P, Brivet M, Nada M, Zabot MT, Mathieu M, Roe C: Mitochondrial very-long-chain acyl-coenzyme A dehydrogenase deficiency: clinical characteristics and diagnostic considerations in 30 patients. Clin Chim Acta. 1998 Jan 12;269(1):43-62. [PubMed:9498103 ]
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]
Zhang X, Li Y, Liang Y, Sun P, Wu X, Song J, Sun X, Hong M, Gao P, Deng D: Distinguishing Intracerebral Hemorrhage from Acute Cerebral Infarction through Metabolomics. Rev Invest Clin. 2017 Nov-Dec;69(6):319-328. doi: 10.24875/RIC.17002348. [PubMed:29265114 ]
Niziol J, Bonifay V, Ossolinski K, Ossolinski T, Ossolinska A, Sunner J, Beech I, Arendowski A, Ruman T: Metabolomic study of human tissue and urine in clear cell renal carcinoma by LC-HRMS and PLS-DA. Anal Bioanal Chem. 2018 Jun;410(16):3859-3869. doi: 10.1007/s00216-018-1059-x. Epub 2018 Apr 16. [PubMed:29658093 ]
Zhao S, Feng XF, Huang T, Luo HH, Chen JX, Zeng J, Gu M, Li J, Sun XY, Sun D, Yang X, Fang ZZ, Cao YF: The Association Between Acylcarnitine Metabolites and Cardiovascular Disease in Chinese Patients With Type 2 Diabetes Mellitus. Front Endocrinol (Lausanne). 2020 May 5;11:212. doi: 10.3389/fendo.2020.00212. eCollection 2020. [PubMed:32431666 ]
Ottas A, Fishman D, Okas TL, Kingo K, Soomets U: The metabolic analysis of psoriasis identifies the associated metabolites while providing computational models for the monitoring of the disease. Arch Dermatol Res. 2017 Sep;309(7):519-528. doi: 10.1007/s00403-017-1760-1. Epub 2017 Jul 10. [PubMed:28695330 ]
Saral NY, Aksungar FB, Aktuglu-Zeybek C, Coskun J, Demirelce O, Serteser M: Glutaric acidemia type II patient with thalassemia minor and novel electron transfer flavoprotein-A gene mutations: A case report and review of literature. World J Clin Cases. 2018 Nov 26;6(14):786-790. doi: 10.12998/wjcc.v6.i14.786. [PubMed:30510944 ]
Yi WJ, Chen J, Li ZB, Jiang TT, Bi DQ, Liu CM, Yang S, Hu YT, Gan L, Tu HH, Huang H, Li JC: Screening of potential biomarkers for Yin-deficiency-heat syndrome based on UHPLC-MS method and the mechanism of Zhibai Dihuang granule therapeutic effect. Anat Rec (Hoboken). 2020 Aug;303(8):2095-2108. doi: 10.1002/ar.24352. Epub 2020 Jan 7. [PubMed:31909891 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for Dodecanoylcarnitine (HMDB0002250)

MOL for HMDB0002250 (Dodecanoylcarnitine)

3D MOL for HMDB0002250 (Dodecanoylcarnitine)

3D SDF for HMDB0002250 (Dodecanoylcarnitine)

3D-SDF for HMDB0002250 (Dodecanoylcarnitine)

PDB for HMDB0002250 (Dodecanoylcarnitine)

3D PDB for HMDB0002250 (Dodecanoylcarnitine)

SMILES for HMDB0002250 (Dodecanoylcarnitine)

INCHI for HMDB0002250 (Dodecanoylcarnitine)

Structure for HMDB0002250 (Dodecanoylcarnitine)

3D Structure for HMDB0002250 (Dodecanoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra