NP-MRD: Showing NP-Card for Decanoylcarnitine (NP0000720)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:23 UTC

NP-MRD ID

NP0000720

Secondary Accession Numbers

None

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

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

decanoylcar.mol
  Mrv1652303062019112D          

 22 21  0  0  0  0            999 V2000
    2.5006    0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.8010    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.6441    1.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -1.0865    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3422   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 12  2  0  0  0  0
  3 18  1  0  0  0  0
  4 18  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 18  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 12  1  1  0  0  0  0
M  CHG  2   3  -1   5   1
M  END
> <DATABASE_ID>
NP0000720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC(=O)OC(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

> <INCHI_KEY>
LZOSYCMHQXPBFU-UHFFFAOYSA-N

> <FORMULA>
C17H33NO4

> <MOLECULAR_WEIGHT>
315.4482

> <EXACT_MASS>
315.240958549

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.57371429635232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
-7.057186892022333

> <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>
(+-)-decanoylcarnitine

> <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                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: decanoylcar.mol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  O   UNK     0       4.668   1.052   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.334  -1.258   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.002   3.362   0.000  0.00  0.00           O-1
HETATM    4  O   UNK     0       8.669   3.362   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.335  -2.028   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0       6.002  -1.258   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.002   0.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.335   1.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.669  -2.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.565  -3.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.105  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334   0.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.001   1.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.667   0.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.667   1.052   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.001   0.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.334   1.052   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.335   2.592   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.668   0.282   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.002   1.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.335   0.282   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.669   1.052   0.000  0.00  0.00           C+0
CONECT    1    7   12                                                       
CONECT    2   12                                                            
CONECT    3   18                                                            
CONECT    4   18                                                            
CONECT    5    6    9   10   11                                             
CONECT    6    5    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7   18                                                       
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    2   13    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   19                                                       
CONECT   18    3    4    8                                                  
CONECT   19   17   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

Synonyms

Value	Source
Decanoyl-L-carnitine	HMDB
Decanoylcarnitine, (+-)-isomer	MeSH, HMDB
Decanoylcarnitine, (R)-isomer	MeSH, HMDB
Decanoylcarnitine, (S)-isomer	MeSH, HMDB

Chemical Formula

C₁₇H₃₃NO₄

Average Mass

315.4482 Da

Monoisotopic Mass

315.24096 Da

IUPAC Name

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

Traditional Name

(+-)-decanoylcarnitine

CAS Registry Number

1492-27-9

SMILES

CCCCCCCCCC(=O)OC(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

InChI Key

LZOSYCMHQXPBFU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens (Urine)	Animalia	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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-acylcarnitine (CHEBI:68830 )

Physical Properties

State

Solid

Experimental 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

Predicted 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	37.57 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022162

KNApSAcK ID

Not Available

Chemspider ID

8420677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

68830

Good Scents ID

rw1896711

References

General References

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 ]

Showing NP-Card for Decanoylcarnitine (NP0000720)

MOL for NP0000720 (Decanoylcarnitine)

3D MOL for NP0000720 (Decanoylcarnitine)

3D SDF for NP0000720 (Decanoylcarnitine)

3D-SDF for NP0000720 (Decanoylcarnitine)

PDB for NP0000720 (Decanoylcarnitine)

3D PDB for NP0000720 (Decanoylcarnitine)

SMILES for NP0000720 (Decanoylcarnitine)

INCHI for NP0000720 (Decanoylcarnitine)

Structure for NP0000720 (Decanoylcarnitine)

3D Structure for NP0000720 (Decanoylcarnitine)