MiMeDB: Showing metabocard for Dodecanoylcarnitine (MMDBc0033535)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:36 UTC

Update Date

2024-04-30 20:12:02 UTC

Metabolite ID

MMDBc0033535

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 [Dambrova et al. 2021, Physiological Reviews], 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 at [Dambrova et al. 2021, Physiological Reviews].

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>
MMDBc0033535

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₉H₃₇NO₄

Average Mass

343.5014

Monoisotopic Mass

343.272258677

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/t17-/m1/s1

InChI Key

FUJLYHJROOYKRA-QGZVFWFLSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9300000000-0cd49618a50984aad982	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-0900000000-1c57ff1372236d823d80	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9000000000-ef35ea7a4d61bac8cb20	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-ce07549e40447c69729f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9005000000-ce18984499544d19b739	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Fibroblasts
Liver
Placenta
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0005073	L-Carnitine	Coenzyme A	Carnitine palmitoyltransferase 1a (liver)	VMH	12828998 9498103 3955080
MMDBr0005127	Dodecanoylcarnitine	Dodecanoylcarnitine	Not Available	VMH	30371894
MMDBr0006705	Dodecanoylcarnitine	Dodecanoylcarnitine	Not Available	VMH	30371894
MMDBr0009754	Coenzyme A	L-Carnitine	Carnitine palmitoyltransferase 1a (liver)	VMH	30371894
MMDBr0009755	L-Carnitine	L-Carnitine	Solute carrier family 22 (organic cation transporter), member 1	VMH	30371894
MMDBr0009756	Coenzyme A	L-Carnitine	Carnitine palmitoyltransferase 2	VMH	30371894
MMDBr0009854	L-Carnitine	L-Carnitine	Solute carrier family 22 (organic cation/carnitine transporter), member 5	VMH	30371894
MMDBr0009855	Coenzyme A	L-Carnitine	Carnitine o-acetyltransferase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Decreased	Association	Human Blood	HMDB	16425363
Very long chain acyl-coa dehydrogenase deficiency	Increased	Association	Human Blood	HMDB	9034211
Obesity	Slight Increase	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity	Slight Increase	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.032	0.002			uM	Adult (>18 years old)	Both	Celiac disease	HMDB	16425363
Human Blood	Detected and Quantified	0.0651	0.0228			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	0.124		0.090	0.162	uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	HMDB	9034211
Human Urine	Detected and Quantified	0.02		0.01	0.04	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			0.03	0.25	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.038		0.005	0.069	uM	Children (1-13 years old)	Both	Normal	HMDB	9034211
Human Blood	Detected and Quantified	0.052	0.004			uM	Adult (>18 years old)	Both	Normal	HMDB	16425363
Human Urine	Detected and Quantified	0.07		0.03	0.14	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.07		0.04	0.28	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.1	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.1	0.04			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Feces	Detected and Quantified	0.42	0.28			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.64	0.3			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.080	0.025			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.086	0.038			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified			0.057	0.190	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.057	0.190	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002250

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0009-8981(92)90106-z. [PubMed:1468155 ]
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 ]
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. doi: 10.1016/s0009-8981(97)00185-x. [PubMed:9498103 ]
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. doi: 10.1006/bbrc.1999.1340. [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. doi: 10.1007/s00216-002-1654-7. Epub 2003 Jan 4. [PubMed:12560963 ]
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. doi: 10.1016/s1570-0232(03)00281-2. [PubMed:12828998 ]
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 ]
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. doi: 10.3748/wjg.v11.i42.6671. [PubMed:16425363 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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Showing metabocard for Dodecanoylcarnitine (MMDBc0033535)

MOL for #<Metabolite:0x00007f55bc0f6cc0>

3D MOL for #<Metabolite:0x00007f55bc0f6cc0>

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Structure for #<Metabolite:0x00007f55bc0f6cc0>

3D Structure for #<Metabolite:0x00007f55bc0f6cc0>