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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-10-24 19:44:10 UTC

HMDB ID

HMDB0000651

Secondary Accession Numbers

HMDB0062631
HMDB00651
HMDB62631

Metabolite Identification

Common Name

Decanoylcarnitine

Description

Decanoylcarnitine is a member of the class of compounds known as acylcarnitines. More specifically, it is a decanoic acid ester of carnitine. Acylcarnitines were first discovered in the 1940s (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. Decanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine decanoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. In particular decanoylcarnitine is elevated in the blood or plasma of individuals with obesity in adolescence (PMID: 26910390 ). It is also decreased in the blood or plasma of individuals with adolescent idiopathic scoliosis (PMID: 26928931 ). Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000651
     RDKit          3D
Decanoylcarnitine
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.3939    0.7328    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -0.0344    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.8736   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697   -0.2270   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5550    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.1382   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.0825   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    0.6523   -2.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    1.4369   -1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    0.6068   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    0.4288    0.8768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.0015   -0.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.7798    0.6294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9744   -2.2073    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -2.9907    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -2.5167    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -4.3413   -0.2506 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9106   -0.1122    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.2702    0.4168 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1620    1.7387    0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182   -0.1946    1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0357   -0.1978   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1202    0.6057    2.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4346    0.3646    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    1.8104    1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7847   -0.6736    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3481    0.7037   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5572   -1.6700    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4997   -1.4951   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.0118   -1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866    0.4861   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.0287    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.4704    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1212    1.8678   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.7080    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5793   -0.6890   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4238   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.1968   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    1.3185   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024    2.2544   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    1.9188   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9715   -0.8049    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -2.4140   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -2.6581    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -0.7748    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    0.8129    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6281    2.0507    1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9232    1.8978   -0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2364    2.2477    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0092   -0.3287    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    0.4650    1.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -1.1861    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6816   -1.1141   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -0.2931   -1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6353    0.5577   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 13 42  1  1
 14 43  1  0
 14 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
M  CHG  2  17  -1  19   1
M  END


  Mrv1652307162122442D          

 22 21  0  0  0  0            999 V2000
   -3.3475   -0.1546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6331   -0.5681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2246   -0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    0.6700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3475    0.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    1.0805    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.7799    0.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9152    1.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535   -0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535   -1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3391   -1.8165    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.7677   -1.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543   -0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842   -0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141   -0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  6  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 17  1  0  0  0  0
M  CHG  2   9   1  15  -1
M  END
> <DATABASE_ID>
HMDB0000651

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3/t15-/m1/s1

> <INCHI_KEY>
LZOSYCMHQXPBFU-OAHLLOKOSA-N

> <FORMULA>
C17H33NO4

> <MOLECULAR_WEIGHT>
315.454

> <EXACT_MASS>
315.240958547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.53098613214002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-0.633864135805079

> <ALOGPS_LOGS>
-6.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022335

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
109.4707

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-decanoyl-L-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000651
     RDKit          3D
Decanoylcarnitine
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.3939    0.7328    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -0.0344    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.8736   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697   -0.2270   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5550    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.1382   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.0825   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    0.6523   -2.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    1.4369   -1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    0.6068   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    0.4288    0.8768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.0015   -0.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.7798    0.6294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9744   -2.2073    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -2.9907    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -2.5167    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -4.3413   -0.2506 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9106   -0.1122    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.2702    0.4168 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1620    1.7387    0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182   -0.1946    1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0357   -0.1978   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1202    0.6057    2.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4346    0.3646    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    1.8104    1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7847   -0.6736    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3481    0.7037   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5572   -1.6700    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4997   -1.4951   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.0118   -1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866    0.4861   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.0287    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.4704    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1212    1.8678   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.7080    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5793   -0.6890   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4238   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.1968   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    1.3185   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024    2.2544   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    1.9188   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9715   -0.8049    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -2.4140   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -2.6581    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -0.7748    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    0.8129    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6281    2.0507    1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9232    1.8978   -0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2364    2.2477    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0092   -0.3287    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    0.4650    1.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -1.1861    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6816   -1.1141   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -0.2931   -1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6353    0.5577   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 13 42  1  1
 14 43  1  0
 14 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
M  CHG  2  17  -1  19   1
M  END

HEADER    PROTEIN                                 16-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-21         0                                  
HETATM    1  C   UNK     0      -6.249  -0.289   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.915  -1.060   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.582  -0.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.250  -1.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.913  -0.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.419  -1.060   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.582   1.251   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.249   1.251   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -7.582   2.017   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0      -8.923   1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.582   3.558   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.175   2.937   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.566  -1.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.566  -2.619   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.233  -3.391   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -8.900  -3.391   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.756  -0.289   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.088  -1.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.425  -0.289   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.757  -1.060   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.094  -0.289   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.426  -1.060   0.000  0.00  0.00           C+0
CONECT    1    2    8   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   17                                                       
CONECT    7    3                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   18    6                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0000651
HETATM    1  C1  UNL     1       6.394   0.733   1.848  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.904  -0.034   0.668  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.925  -0.874  -0.037  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.770  -0.227  -0.713  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.843   0.555   0.138  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.676   1.138  -0.684  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.862   0.082  -1.345  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.702   0.652  -2.137  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.260   1.437  -1.311  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.873   0.607  -0.221  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.269   0.429   0.877  1.00  0.00           O  
HETATM   12  O2  UNL     1      -2.089  -0.002  -0.325  1.00  0.00           O  
HETATM   13  C11 UNL     1      -2.714  -0.780   0.629  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.974  -2.207   0.325  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.745  -2.991   0.044  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.587  -2.517   0.055  1.00  0.00           O  
HETATM   17  O4  UNL     1      -1.881  -4.341  -0.251  1.00  0.00           O1-
HETATM   18  C14 UNL     1      -3.911  -0.112   1.245  1.00  0.00           C  
HETATM   19  N1  UNL     1      -4.976   0.270   0.417  1.00  0.00           N1+
HETATM   20  C15 UNL     1      -5.162   1.739   0.388  1.00  0.00           C  
HETATM   21  C16 UNL     1      -6.218  -0.195   1.075  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.036  -0.198  -0.918  1.00  0.00           C  
HETATM   23  H1  UNL     1       7.120   0.606   2.726  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.435   0.365   2.236  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.366   1.810   1.606  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.785  -0.674   1.005  1.00  0.00           H  
HETATM   27  H5  UNL     1       7.348   0.704  -0.060  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.557  -1.670   0.682  1.00  0.00           H  
HETATM   29  H7  UNL     1       6.500  -1.495  -0.789  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.180  -1.012  -1.260  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.187   0.486  -1.483  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.432   0.029   1.005  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.378   1.470   0.505  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.121   1.868  -1.390  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.075   1.708   0.054  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.579  -0.689  -0.629  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.503  -0.424  -2.128  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.171  -0.197  -2.593  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.130   1.318  -2.896  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.302   2.254  -0.792  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.014   1.919  -1.929  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.971  -0.805   1.500  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.776  -2.414  -0.407  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.374  -2.658   1.286  1.00  0.00           H  
HETATM   45  H23 UNL     1      -4.225  -0.775   2.101  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.519   0.813   1.765  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.628   2.051   1.338  1.00  0.00           H  
HETATM   48  H26 UNL     1      -5.923   1.898  -0.406  1.00  0.00           H  
HETATM   49  H27 UNL     1      -4.236   2.248   0.133  1.00  0.00           H  
HETATM   50  H28 UNL     1      -7.009  -0.329   0.319  1.00  0.00           H  
HETATM   51  H29 UNL     1      -6.495   0.465   1.902  1.00  0.00           H  
HETATM   52  H30 UNL     1      -5.961  -1.186   1.507  1.00  0.00           H  
HETATM   53  H31 UNL     1      -5.682  -1.114  -0.982  1.00  0.00           H  
HETATM   54  H32 UNL     1      -4.099  -0.293  -1.464  1.00  0.00           H  
HETATM   55  H33 UNL     1      -5.635   0.558  -1.514  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   18   42
CONECT   14   15   43   44
CONECT   15   16   16   17
CONECT   18   19   45   46
CONECT   19   20   21   22
CONECT   20   47   48   49
CONECT   21   50   51   52
CONECT   22   53   54   55
END

HMDB0000651
     RDKit          3D
Decanoylcarnitine
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.3939    0.7328    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -0.0344    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.8736   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697   -0.2270   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5550    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.1382   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.0825   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    0.6523   -2.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    1.4369   -1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    0.6068   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    0.4288    0.8768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.0015   -0.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.7798    0.6294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9744   -2.2073    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -2.9907    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -2.5167    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -4.3413   -0.2506 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9106   -0.1122    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.2702    0.4168 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1620    1.7387    0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182   -0.1946    1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0357   -0.1978   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1202    0.6057    2.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4346    0.3646    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    1.8104    1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7847   -0.6736    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3481    0.7037   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5572   -1.6700    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4997   -1.4951   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.0118   -1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866    0.4861   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.0287    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.4704    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1212    1.8678   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.7080    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5793   -0.6890   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4238   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.1968   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    1.3185   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024    2.2544   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    1.9188   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9715   -0.8049    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -2.4140   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -2.6581    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -0.7748    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    0.8129    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6281    2.0507    1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9232    1.8978   -0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2364    2.2477    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0092   -0.3287    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    0.4650    1.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -1.1861    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6816   -1.1141   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -0.2931   -1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6353    0.5577   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 13 42  1  1
 14 43  1  0
 14 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
M  CHG  2  17  -1  19   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Decanoylcarnitine	ChEBI
O-Decanoyl-(R)-carnitine	ChEBI
O-Decanoyl-R-carnitine	ChEBI
Decanoyl-L-carnitine	HMDB

Chemical Formula

C₁₇H₃₃NO₄

Average Molecular Weight

315.454

Monoisotopic Molecular Weight

315.240958547

IUPAC Name

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

Traditional Name

O-decanoyl-L-carnitine

CAS Registry Number

1492-27-9

SMILES

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

InChI Identifier

InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3/t15-/m1/s1

InChI Key

LZOSYCMHQXPBFU-OAHLLOKOSA-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:28717 )
O-decanoylcarnitine (CHEBI:28717 )
Fatty acyl carnitines (C03299 )
Fatty acyl carnitines (LMFA07070006 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0062631)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	350.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	-0.85	ALOGPS
logP	-0.63	ChemAxon
logS	-6.4	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	14	ChemAxon
Refractivity	109.47 m³·mol⁻¹	ChemAxon
Polarizability	37.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	186.974	32859911
AllCCS	[M-H]-	187.032	32859911
DeepCCS	[M+H]+	194.8	30932474
DeepCCS	[M-H]-	190.781	30932474
DeepCCS	[M-2H]-	227.324	30932474
DeepCCS	[M+Na]+	203.616	30932474
AllCCS	[M+H]+	187.0	32859911
AllCCS	[M+H-H2O]+	184.4	32859911
AllCCS	[M+NH4]+	189.3	32859911
AllCCS	[M+Na]+	190.0	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	189.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Decanoylcarnitine	CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2537.8	Standard polar	33892256
Decanoylcarnitine	CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1821.2	Standard non polar	33892256
Decanoylcarnitine	CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2061.1	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 - Decanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Decanoylcarnitine 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 - Decanoylcarnitine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014r-7029000000-c5e89a545ccedb00aa9f	2021-07-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-03di-9100000000-51ec5fbc3590afaa7d94	2021-07-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-e8d414ba473e4495a085	2021-07-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 10V, Positive-QTOF	splash10-014i-0009000000-88086c5f1e51320ffee2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 30V, Positive-QTOF	splash10-000i-9000000000-cc559c3ec2ad03f7cf62	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 30V, Positive-QTOF	splash10-000i-9000000000-805db73ae9d3d6fc6639	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 0V, Positive-QTOF	splash10-014i-0009000000-db05aac6a1f5fa9fa512	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 10V, Positive-QTOF	splash10-014i-1019000000-b32d4102d6ac5bf03c9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Decanoylcarnitine 0V, Positive-QTOF	splash10-014i-0009000000-089552ddd13a301e2a50	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decanoylcarnitine 10V, Positive-QTOF	splash10-014i-0009000000-f21bb9548b858bf2d426	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decanoylcarnitine 20V, Positive-QTOF	splash10-00kr-9005000000-7eba8106d0ab229b8c08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2021-07-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2021-07-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.26 +/- 0.11 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.141 +/- 0.009 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	<0.3 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Blood	Detected and Quantified	0.16-0.55 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.12 (0.11-0.14) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	0.36 (0.29-0.5) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	0.23(0.09) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	0.31 +/- 0.13 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	0.16-0.55 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.005 (0.0-0.124) uM	Children (1-13 years old)	Both	Normal	9034211	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected and Quantified	0.91 +/- 0.43 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	1.54 +/- 0.78 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.04 (0.02–0.06) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.04-0.13 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.06(0.04-0.14) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.06(0.04-0.09) 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
Urine	Detected and Quantified	0.0699 +/- 0.0206 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.103 +/- 0.008 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details
Blood	Detected and Quantified	0.72 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	1.09 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.1267 (0.0743) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.2449 (0.1076) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.31(0.13) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.230 +/- 0.067 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.259 +/- 0.113 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.005 (0.0-0.012) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.0673 +/- 0.0193 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0821 +/- 0.0263 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	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 ]
Glutaric aciduria II
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Obesity
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.
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
231680 (Glutaric aciduria II)
601665 (Obesity)
266600 (Crohn's disease)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953821

PDB ID

Not Available

ChEBI ID

28717

Food Biomarker Ontology

Not Available

VMH ID

C10CRN

MarkerDB ID

MDB00000208

Good Scents ID

rw1896711

References

Synthesis Reference

Strack, Erich; Mueller, Detlef M. Preparation of O-acylcarnitines. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1970), 351(1), 95-8.

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 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
Schmidt-Sommerfeld E, Penn D, Duran M, Bennett MJ, Santer R, Stanley CA: Detection of inborn errors of fatty acid oxidation from acylcarnitine analysis of plasma and blood spots with the radioisotopic exchange-high-performance liquid chromatographic method. J Pediatr. 1993 May;122(5 Pt 1):708-14. [PubMed:8496747 ]
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 ]
Wang C, Feng R, Sun D, Li Y, Bi X, Sun C: Metabolic profiling of urine in young obese men using ultra performance liquid chromatography and Q-TOF mass spectrometry (UPLC/Q-TOF MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Oct 1;879(27):2871-6. doi: 10.1016/j.jchromb.2011.08.014. Epub 2011 Aug 22. [PubMed:21890434 ]
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Xiao JF, Varghese RS, Zhou B, Nezami Ranjbar MR, Zhao Y, Tsai TH, Di Poto C, Wang J, Goerlitz D, Luo Y, Cheema AK, Sarhan N, Soliman H, Tadesse MG, Ziada DH, Ressom HW: LC-MS based serum metabolomics for identification of hepatocellular carcinoma biomarkers in Egyptian cohort. J Proteome Res. 2012 Dec 7;11(12):5914-23. doi: 10.1021/pr300673x. Epub 2012 Nov 1. [PubMed:23078175 ]
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
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 ]
Sun ZJ, Jia HM, Qiu GX, Zhou C, Guo S, Zhang JG, Shen JX, Zhao Y, Zou ZM: Identification of candidate diagnostic biomarkers for adolescent idiopathic scoliosis using UPLC/QTOF-MS analysis: a first report of lipid metabolism profiles. Sci Rep. 2016 Mar 1;6:22274. doi: 10.1038/srep22274. [PubMed:26928931 ]
Adams SH, Hoppel CL, Lok KH, Zhao L, Wong SW, Minkler PE, Hwang DH, Newman JW, Garvey WT: Plasma acylcarnitine profiles suggest incomplete long-chain fatty acid beta-oxidation and altered tricarboxylic acid cycle activity in type 2 diabetic African-American women. J Nutr. 2009 Jun;139(6):1073-81. doi: 10.3945/jn.108.103754. Epub 2009 Apr 15. [PubMed:19369366 ]
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Showing metabocard for Decanoylcarnitine (HMDB0000651)

MOL for HMDB0000651 (Decanoylcarnitine)

3D MOL for HMDB0000651 (Decanoylcarnitine)

3D SDF for HMDB0000651 (Decanoylcarnitine)

3D-SDF for HMDB0000651 (Decanoylcarnitine)

PDB for HMDB0000651 (Decanoylcarnitine)

3D PDB for HMDB0000651 (Decanoylcarnitine)

SMILES for HMDB0000651 (Decanoylcarnitine)

INCHI for HMDB0000651 (Decanoylcarnitine)

Structure for HMDB0000651 (Decanoylcarnitine)

3D Structure for HMDB0000651 (Decanoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra