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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-23 13:16:22 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005066

Secondary Accession Numbers

HMDB05066

Metabolite Identification

Common Name

Tetradecanoylcarnitine

Description

Tetradecanoylcarnitine, also known as myristoylcarnitine, is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acylcarnitines are useful in the diagnosis of genetic disorders such as fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency disorders (PMID: 12385891 ). Tetradecanoylcarnitine is involved in the beta-oxidation of long-chain fatty acids (PMID: 16425363 ). Tetradecanoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.

Structure

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

  Mrv1652311141918182D          

 26 25  0  0  0  0            999 V2000
 9995.3919 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.1059 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8199 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5339 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2479 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9619 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6759 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3908 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.1044 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8180 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.819910000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.391910000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.677910001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.959810000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.677910001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.824910001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6862 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6862 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4002 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9993.9722 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5330 9999.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2469 9999.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9619 9999.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.6758 9999.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3909 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.1048 9999.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  6  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  2  13   1  19  -1
M  END

HMDB0005066
     RDKit          3D
Tetradecanoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.2195   -2.8159    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.6553    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828   -1.4594    1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060   -0.2367    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    1.0268    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100    2.1992    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    2.3417   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206    2.5618    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    2.6909   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    2.9093   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    3.0538   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    1.8204   -2.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.5806   -1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424    0.6318   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5803   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4510   -0.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7029   -0.4964    0.0346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4775   -0.6989    1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3785    2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.3809    1.5658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    0.2746    3.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694   -1.6871   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6917   -1.9857   -0.1554 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6760   -3.1513    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4426   -0.9573    0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702   -2.4783   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379   -3.9143    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -2.3378    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620   -2.4598   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -2.4933   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934   -3.5600    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4899   -1.6120    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.3918    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -0.3236    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3607   -0.1893   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    1.1448    2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781    0.9498    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    3.1168    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    2.0150    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    3.2671   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4789    1.5234   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.7004    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    3.5324    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398    3.6039   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2457    1.7687   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    2.0692    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    3.8499    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    3.9327   -2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265    3.3202   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    1.6611   -3.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    1.9092   -3.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -0.3186   -2.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.4045   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    0.4596   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -1.6474    1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309   -0.8633    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.9461    4.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -1.6144   -1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142   -2.5700   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608   -4.0821    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6268   -3.1688    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7806   -3.1320    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7116   -1.2756    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4597   -0.8574   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.0139    0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -1.9874   -2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3538   -3.5584   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5286   -2.1886   -1.2223 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 17 54  1  1
 18 55  1  0
 18 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
M  CHG  1  23   1
M  END

  Mrv1652311141918182D          

 26 25  0  0  0  0            999 V2000
 9995.3919 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.1059 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8199 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5339 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2479 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9619 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6759 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3908 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.1044 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8180 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.819910000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.391910000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.677910001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.959810000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.677910001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.824910001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6862 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6862 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4002 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9993.9722 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5330 9999.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2469 9999.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9619 9999.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.6758 9999.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3909 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.1048 9999.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  6  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  2  13   1  19  -1
M  END
> <DATABASE_ID>
HMDB0005066

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h19H,5-18H2,1-4H3/t19-/m1/s1

> <INCHI_KEY>
PSHXNVGSVNEJBD-LJQANCHMSA-N

> <FORMULA>
C21H41NO4

> <MOLECULAR_WEIGHT>
371.5545

> <EXACT_MASS>
371.303558805

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.0552903900023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
1.1444105241949205

> <ALOGPS_LOGS>
-7.40

> <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>
127.87469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-(tetradecanoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005066
     RDKit          3D
Tetradecanoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.2195   -2.8159    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.6553    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828   -1.4594    1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060   -0.2367    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    1.0268    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100    2.1992    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    2.3417   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206    2.5618    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    2.6909   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    2.9093   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    3.0538   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    1.8204   -2.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.5806   -1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424    0.6318   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5803   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4510   -0.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7029   -0.4964    0.0346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4775   -0.6989    1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3785    2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.3809    1.5658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    0.2746    3.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694   -1.6871   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6917   -1.9857   -0.1554 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6760   -3.1513    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4426   -0.9573    0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702   -2.4783   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379   -3.9143    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -2.3378    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620   -2.4598   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -2.4933   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934   -3.5600    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4899   -1.6120    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.3918    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -0.3236    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3607   -0.1893   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    1.1448    2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781    0.9498    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    3.1168    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    2.0150    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    3.2671   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4789    1.5234   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.7004    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    3.5324    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398    3.6039   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2457    1.7687   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    2.0692    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    3.8499    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    3.9327   -2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265    3.3202   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    1.6611   -3.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    1.9092   -3.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -0.3186   -2.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.4045   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    0.4596   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -1.6474    1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309   -0.8633    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.9461    4.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -1.6144   -1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142   -2.5700   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608   -4.0821    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6268   -3.1688    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7806   -3.1320    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7116   -1.2756    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4597   -0.8574   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.0139    0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -1.9874   -2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3538   -3.5584   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5286   -2.1886   -1.2223 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 17 54  1  1
 18 55  1  0
 18 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
M  CHG  1  23   1
M  END

HEADER    PROTEIN                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0    8658.0658666.276   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8659.3988665.504   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.7308666.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.0638665.504   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3968666.276   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.7298665.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.0628666.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.3968665.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.7288666.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.0608665.504   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8660.7308667.815   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8658.0658667.815   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8656.7328668.581   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0    8655.3928667.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8656.7328670.121   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8655.1408669.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8656.7488665.485   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8656.7488663.947   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8658.0808663.175   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0    8655.4158663.175   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8671.3958666.273   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7288665.501   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.0628666.269   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8675.3958665.497   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8676.7308666.265   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8678.0628665.493   0.000  0.00  0.00           C+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
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   21                                                       
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0005066
HETATM    1  C1  UNL     1       6.219  -2.816   0.085  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.844  -2.655   0.705  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.783  -1.459   1.631  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.106  -0.237   0.825  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.073   1.027   1.659  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.410   2.199   0.763  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.433   2.342  -0.368  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.021   2.562   0.140  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.117   2.691  -1.096  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.722   2.909  -0.603  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.215   3.054  -1.759  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.189   1.820  -2.608  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.583   0.581  -1.856  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.942   0.632  -1.302  1.00  0.00           C  
HETATM   15  O1  UNL     1      -2.717   1.580  -1.459  1.00  0.00           O  
HETATM   16  O2  UNL     1      -2.385  -0.451  -0.556  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.703  -0.496   0.035  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.477  -0.699   1.514  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.690   0.379   2.147  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.230   1.381   1.566  1.00  0.00           O  
HETATM   21  O4  UNL     1      -2.434   0.275   3.508  1.00  0.00           O  
HETATM   22  C18 UNL     1      -4.369  -1.687  -0.565  1.00  0.00           C  
HETATM   23  N1  UNL     1      -5.692  -1.986  -0.155  1.00  0.00           N1+
HETATM   24  C19 UNL     1      -5.676  -3.151   0.753  1.00  0.00           C  
HETATM   25  C20 UNL     1      -6.443  -0.957   0.478  1.00  0.00           C  
HETATM   26  C21 UNL     1      -6.470  -2.478  -1.316  1.00  0.00           C  
HETATM   27  H1  UNL     1       6.438  -3.914   0.042  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.004  -2.338   0.716  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.262  -2.460  -0.959  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.100  -2.493  -0.106  1.00  0.00           H  
HETATM   31  H5  UNL     1       4.593  -3.560   1.299  1.00  0.00           H  
HETATM   32  H6  UNL     1       5.490  -1.612   2.471  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.759  -1.392   2.016  1.00  0.00           H  
HETATM   34  H8  UNL     1       6.095  -0.324   0.369  1.00  0.00           H  
HETATM   35  H9  UNL     1       4.361  -0.189  -0.005  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.117   1.145   2.184  1.00  0.00           H  
HETATM   37  H11 UNL     1       5.878   0.950   2.416  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.406   3.117   1.364  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.404   2.015   0.342  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.736   3.267  -0.931  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.479   1.523  -1.105  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.679   1.700   0.746  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.957   3.532   0.667  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.440   3.604  -1.641  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.246   1.769  -1.661  1.00  0.00           H  
HETATM   46  H20 UNL     1       0.391   2.069   0.059  1.00  0.00           H  
HETATM   47  H21 UNL     1       0.684   3.850   0.025  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.145   3.933  -2.351  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.227   3.320  -1.382  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.810   1.661  -3.051  1.00  0.00           H  
HETATM   51  H25 UNL     1      -0.909   1.909  -3.469  1.00  0.00           H  
HETATM   52  H26 UNL     1      -0.540  -0.319  -2.524  1.00  0.00           H  
HETATM   53  H27 UNL     1       0.152   0.404  -1.027  1.00  0.00           H  
HETATM   54  H28 UNL     1      -4.150   0.460  -0.230  1.00  0.00           H  
HETATM   55  H29 UNL     1      -2.896  -1.647   1.700  1.00  0.00           H  
HETATM   56  H30 UNL     1      -4.431  -0.863   2.074  1.00  0.00           H  
HETATM   57  H31 UNL     1      -2.811   0.946   4.168  1.00  0.00           H  
HETATM   58  H32 UNL     1      -4.355  -1.614  -1.693  1.00  0.00           H  
HETATM   59  H33 UNL     1      -3.714  -2.570  -0.341  1.00  0.00           H  
HETATM   60  H34 UNL     1      -5.661  -4.082   0.143  1.00  0.00           H  
HETATM   61  H35 UNL     1      -6.627  -3.169   1.324  1.00  0.00           H  
HETATM   62  H36 UNL     1      -4.781  -3.132   1.405  1.00  0.00           H  
HETATM   63  H37 UNL     1      -6.712  -1.276   1.514  1.00  0.00           H  
HETATM   64  H38 UNL     1      -7.460  -0.857  -0.021  1.00  0.00           H  
HETATM   65  H39 UNL     1      -5.951   0.014   0.446  1.00  0.00           H  
HETATM   66  H40 UNL     1      -6.032  -1.987  -2.220  1.00  0.00           H  
HETATM   67  H41 UNL     1      -6.354  -3.558  -1.447  1.00  0.00           H  
HETATM   68  H42 UNL     1      -7.529  -2.189  -1.222  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   22   54
CONECT   18   19   55   56
CONECT   19   20   20   21
CONECT   21   57
CONECT   22   23   58   59
CONECT   23   24   25   26
CONECT   24   60   61   62
CONECT   25   63   64   65
CONECT   26   66   67   68
END

HMDB0005066
     RDKit          3D
Tetradecanoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.2195   -2.8159    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.6553    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828   -1.4594    1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060   -0.2367    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    1.0268    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100    2.1992    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    2.3417   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206    2.5618    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    2.6909   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    2.9093   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    3.0538   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    1.8204   -2.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.5806   -1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424    0.6318   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5803   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4510   -0.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7029   -0.4964    0.0346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4775   -0.6989    1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3785    2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.3809    1.5658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    0.2746    3.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694   -1.6871   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6917   -1.9857   -0.1554 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6760   -3.1513    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4426   -0.9573    0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702   -2.4783   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379   -3.9143    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -2.3378    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620   -2.4598   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -2.4933   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934   -3.5600    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4899   -1.6120    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.3918    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -0.3236    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3607   -0.1893   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    1.1448    2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781    0.9498    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    3.1168    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    2.0150    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    3.2671   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4789    1.5234   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.7004    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    3.5324    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398    3.6039   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2457    1.7687   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    2.0692    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    3.8499    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    3.9327   -2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265    3.3202   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    1.6611   -3.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    1.9092   -3.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -0.3186   -2.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.4045   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    0.4596   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -1.6474    1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309   -0.8633    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.9461    4.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -1.6144   -1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142   -2.5700   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608   -4.0821    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6268   -3.1688    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7806   -3.1320    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7116   -1.2756    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4597   -0.8574   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.0139    0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -1.9874   -2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3538   -3.5584   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5286   -2.1886   -1.2223 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 17 54  1  1
 18 55  1  0
 18 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
M  CHG  1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Myristoylcarnitine	ChEBI
(-)-Tetradecanoylcarnitine	ChEBI
(R)-Myristoylcarnitine	ChEBI
(R)-Tetradecanoylcarnitine	ChEBI
L-Myristoylcarnitine	ChEBI
Myristoyl-L-(-)-carnitine	ChEBI
Myristoyl-L-carnitine	ChEBI
Myristoylcarnitine	ChEBI
O-Tetradecanoyl-(R)-carnitine	ChEBI
Tetradecanoyl-L-carnitine	ChEBI
C14 Carnitine	HMDB
Tetradecanoylcarnitine	HMDB

Chemical Formula

C₂₁H₄₂NO₄

Average Molecular Weight

372.569

Monoisotopic Molecular Weight

372.310835257

IUPAC Name

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

Traditional Name

(3R)-3-(tetradecanoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

25597-07-3

SMILES

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

InChI Identifier

InChI=1S/C21H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h19H,5-18H2,1-4H3/p+1/t19-/m1/s1

InChI Key

PSHXNVGSVNEJBD-LJQANCHMSA-O

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:84634 )
O-tetradecanoylcarnitine (CHEBI:84634 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Very Long Chain Acyl-CoA Dehydrogenase Deficiency (HMDB: HMDB0005066)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9034211)
Saliva (HMDB: HMDB0005066)

Cellular substructure

Organ

Placenta (HMDB: HMDB0005066)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005066)

Source

Endogenous

Endogenous (HMDB: HMDB0005066)

Animal

Animal (HMDB: HMDB0005066)

Exogenous

Food

Food (HMDB: HMDB0005066)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Exogenous (HMDB: HMDB0005066)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0005066)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0005066)

Lipid metabolism pathway (HMDB: HMDB0005066)

Cellular process

Cell signaling (HMDB: HMDB0005066)

Biochemical process

Lipid transport (HMDB: HMDB0005066)

Role

Biological role

Energy source (HMDB: HMDB0005066)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0005066)

Pharmaceutical industry

Biomarker

Pregnancy (MarkerDB: MDB00000468)
Obesity (MarkerDB: MDB00000468)
Glutaric Acidemia Type 2 (MarkerDB: MDB00000468)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.7e-05 g/L	ALOGPS
logP	0.86	ALOGPS
logP	1.14	ChemAxon
logS	-7.4	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	18	ChemAxon
Refractivity	127.87 m³·mol⁻¹	ChemAxon
Polarizability	46.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	206.759	30932474
DeepCCS	[M-H]-	202.739	30932474
DeepCCS	[M-2H]-	239.282	30932474
DeepCCS	[M+Na]+	215.574	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetradecanoylcarnitine	CCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3545.2	Standard polar	33892256
Tetradecanoylcarnitine	CCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2350.4	Standard non polar	33892256
Tetradecanoylcarnitine	CCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2582.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetradecanoylcarnitine,1TMS,isomer #1	CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2601.0	Semi standard non polar	33892256
Tetradecanoylcarnitine,1TBDMS,isomer #1	CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	2833.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetradecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9310000000-80762110d17332491ce0	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetradecanoylcarnitine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 10V, Positive-QTOF	splash10-00di-0009000000-ebacd89483d3e5c1fe24	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 20V, Positive-QTOF	splash10-0079-9005000000-55ccdfe0f24295822965	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
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	0.04 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.030-0.070 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.030-0.070 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.02 +/- 0.02 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	0.01 +/- 0.01 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.05(0.01) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	<0.18 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Blood	Detected and Quantified	0.016 (0.002-0.043) uM	Children (1-13 years old)	Both	Normal	9034211	details
Feces	Detected and Quantified	0.54 +/- 0.47 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.32 +/- 0.29 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.056 +/- 0.056 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.018 (0.001-0.088) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.01-0.09 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.02(0.01-0.09) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.02(0.01-0.07) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.719 (0.478-0.983) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Blood	Detected and Quantified	0.02 +/- 0.02 uM	Children (1-13 years old)	Both	Acetaminophen overdose	24521011	details
Blood	Detected and Quantified	0.05(0.01) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.0337 (0.0126) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.0403 (0.0065) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.043 +/- 0.015 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.047 +/- 0.018 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.3 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.92 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details

Associated Disorders and Diseases

Disease References

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.

Associated OMIM IDs

201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
231680 (Glutaric aciduria II)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023615

KNApSAcK ID

C00052417

Chemspider ID

30776567

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477791

PDB ID

Not Available

ChEBI ID

84634

Food Biomarker Ontology

Not Available

VMH ID

M02973

MarkerDB ID

MDB00000468

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
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 ]
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 ]

Showing metabocard for Tetradecanoylcarnitine (HMDB0005066)

MOL for HMDB0005066 (Tetradecanoylcarnitine)

3D MOL for HMDB0005066 (Tetradecanoylcarnitine)

3D SDF for HMDB0005066 (Tetradecanoylcarnitine)

3D-SDF for HMDB0005066 (Tetradecanoylcarnitine)

PDB for HMDB0005066 (Tetradecanoylcarnitine)

3D PDB for HMDB0005066 (Tetradecanoylcarnitine)

SMILES for HMDB0005066 (Tetradecanoylcarnitine)

INCHI for HMDB0005066 (Tetradecanoylcarnitine)

Structure for HMDB0005066 (Tetradecanoylcarnitine)

3D Structure for HMDB0005066 (Tetradecanoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra