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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-05-23 00:20:16 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006319

Secondary Accession Numbers

HMDB06319

Metabolite Identification

Common Name

Alpha-linolenyl carnitine

Description

alpha-linolenyl carnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).

Structure

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


  Mrv1652307191923442D          

 30 29  0  0  1  0            999 V2000
   14.1773   -3.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8918   -3.1401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4628   -3.1401    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.7484   -2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0503   -3.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8753   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6063   -3.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3208   -3.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3208   -2.3151    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.0353   -3.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8866   -2.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7419   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4563   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1708   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8853   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5998   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3143   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0287   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7432   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4577   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1721   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1721   -0.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  9  8  1  0  0  0  0
  8 10  2  0  0  0  0
  7  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  2  0  0  0  0
 11 29  1  0  0  0  0
  2 11  1  1  0  0  0
M  CHG  2   3   1   9  -1
M  END

HMDB0006319
     RDKit          3D
Alpha-linolenyl carnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    9.4722   -0.5279   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1899    0.1273    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   -0.9652    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416   -1.2379    1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876   -0.5339    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4517    0.7137    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    0.9060    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -0.0262   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5834   -1.4086   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283   -1.9893    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.3108    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -2.0048    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -1.3824    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3056    0.0355   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    0.3163   -1.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -0.1840   -2.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097    0.3249   -2.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    0.0450   -1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -1.0225   -0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    1.0098   -1.0091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    0.6563    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4596    1.6925    1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387    1.6293    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617    0.5415    3.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832    2.7986    3.2360 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3313    0.8914   -0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5167    0.6943    0.3308 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.0503    2.0199    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5939    0.1936   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5833   -0.1252    1.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5231    0.2408   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4256   -1.0859   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6949   -1.2896   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1904    0.6161    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4907    0.9230   -0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8725   -1.6706    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -2.1571    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6620   -0.2077    3.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8204   -1.2178    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0553    1.6368    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741    1.9825   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.4614   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141   -0.0241   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858   -2.0716   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683   -3.0585    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5195    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -0.2472    0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -1.8582   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816   -3.0715    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025   -2.0657   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -1.3715    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.4363    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759    0.6229    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    0.0764   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929    1.4562   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.2977   -2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.0972   -3.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    1.4199   -2.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -0.1380   -3.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.3580    0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.6340    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.7056    0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3653    1.9608   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4379    0.3036   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1353    2.6345   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9945    1.9421    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3082    2.5394    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5683   -0.9146   -0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5389    0.4696   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5577    0.6891   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8203   -0.9078    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5771   -0.6739    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6348    0.4811    2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  1
 22 61  1  0
 22 62  1  0
 26 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 30 73  1  0
M  CHG  2  25  -1  27   1
M  END


  Mrv1652307191923442D          

 30 29  0  0  1  0            999 V2000
   14.1773   -3.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8918   -3.1401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4628   -3.1401    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.7484   -2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0503   -3.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8753   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6063   -3.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3208   -3.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3208   -2.3151    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.0353   -3.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8866   -2.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7419   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4563   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1708   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8853   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5998   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3143   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0287   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7432   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4577   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1721   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1721   -0.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  9  8  1  0  0  0  0
  8 10  2  0  0  0  0
  7  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  2  0  0  0  0
 11 29  1  0  0  0  0
  2 11  1  1  0  0  0
M  CHG  2   3   1   9  -1
M  END
> <DATABASE_ID>
HMDB0006319

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h6-7,9-10,12-13,23H,5,8,11,14-22H2,1-4H3/b7-6-,10-9-,13-12-/t23-/m0/s1

> <INCHI_KEY>
WJCRATGUUISKDG-UHMZJXMFSA-N

> <FORMULA>
C25H43NO4

> <MOLECULAR_WEIGHT>
421.622

> <EXACT_MASS>
421.319208869

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.03731444629987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.8369202141949204

> <ALOGPS_LOGS>
-7.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022398

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
149.62850000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006319
     RDKit          3D
Alpha-linolenyl carnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    9.4722   -0.5279   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1899    0.1273    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   -0.9652    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416   -1.2379    1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876   -0.5339    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4517    0.7137    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    0.9060    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -0.0262   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5834   -1.4086   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283   -1.9893    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.3108    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -2.0048    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -1.3824    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3056    0.0355   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    0.3163   -1.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -0.1840   -2.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097    0.3249   -2.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    0.0450   -1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -1.0225   -0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    1.0098   -1.0091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    0.6563    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4596    1.6925    1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387    1.6293    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617    0.5415    3.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832    2.7986    3.2360 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3313    0.8914   -0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5167    0.6943    0.3308 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.0503    2.0199    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5939    0.1936   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5833   -0.1252    1.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5231    0.2408   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4256   -1.0859   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6949   -1.2896   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1904    0.6161    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4907    0.9230   -0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8725   -1.6706    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -2.1571    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6620   -0.2077    3.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8204   -1.2178    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0553    1.6368    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741    1.9825   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.4614   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141   -0.0241   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858   -2.0716   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683   -3.0585    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5195    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -0.2472    0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -1.8582   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816   -3.0715    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025   -2.0657   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -1.3715    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.4363    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759    0.6229    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    0.0764   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929    1.4562   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.2977   -2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.0972   -3.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    1.4199   -2.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -0.1380   -3.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.3580    0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.6340    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.7056    0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3653    1.9608   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4379    0.3036   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1353    2.6345   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9945    1.9421    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3082    2.5394    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5683   -0.9146   -0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5389    0.4696   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5577    0.6891   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8203   -0.9078    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5771   -0.6739    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6348    0.4811    2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  1
 22 61  1  0
 22 62  1  0
 26 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 30 73  1  0
M  CHG  2  25  -1  27   1
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0      26.464  -6.632   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.798  -5.862   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      25.131  -5.862   0.000  0.00  0.00           N+1
HETATM    4  C   UNK     0      23.797  -5.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.361  -7.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.901  -4.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.132  -6.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.465  -5.862   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      30.465  -4.322   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      31.799  -6.632   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.788  -4.114   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.782  -3.344   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.116  -4.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.449  -3.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.783  -3.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.117  -4.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.451  -3.344   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.784  -3.344   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.118  -4.114   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.452  -3.344   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.785  -3.344   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.119  -4.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.453  -3.344   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.786  -4.114   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.120  -3.344   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.454  -4.114   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.787  -3.344   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.121  -4.114   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.455  -3.344   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      26.455  -1.804   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7   11                                                  
CONECT    3    1    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    2    8                                                       
CONECT    8    9   10    7                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   29    2                                                       
CONECT   12   13                                                            
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   11                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0006319
HETATM    1  C1  UNL     1       9.472  -0.528  -1.317  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.190   0.127   0.061  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.975  -0.965   0.997  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.942  -1.238   1.730  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.688  -0.534   1.845  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.452   0.714   1.133  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.577   0.906   0.181  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.634  -0.026  -0.423  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.583  -1.409  -0.046  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.528  -1.989   0.490  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.269  -1.311   0.775  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.165  -2.005   0.000  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.201  -1.382   0.255  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.306   0.035  -0.163  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.098   0.316  -1.587  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.023  -0.184  -2.615  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.410   0.325  -2.629  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.248   0.045  -1.474  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.217  -1.023  -0.855  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.145   1.010  -1.009  1.00  0.00           O  
HETATM   21  C19 UNL     1      -4.971   0.656   0.191  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.460   1.693   1.165  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.939   1.629   2.538  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.062   0.541   3.148  1.00  0.00           O  
HETATM   25  O4  UNL     1      -5.283   2.799   3.236  1.00  0.00           O1-
HETATM   26  C22 UNL     1      -6.331   0.891  -0.360  1.00  0.00           C  
HETATM   27  N1  UNL     1      -7.517   0.694   0.331  1.00  0.00           N1+
HETATM   28  C23 UNL     1      -8.050   2.020   0.727  1.00  0.00           C  
HETATM   29  C24 UNL     1      -8.594   0.194  -0.573  1.00  0.00           C  
HETATM   30  C25 UNL     1      -7.583  -0.125   1.479  1.00  0.00           C  
HETATM   31  H1  UNL     1       9.523   0.241  -2.093  1.00  0.00           H  
HETATM   32  H2  UNL     1      10.426  -1.086  -1.198  1.00  0.00           H  
HETATM   33  H3  UNL     1       8.695  -1.290  -1.523  1.00  0.00           H  
HETATM   34  H4  UNL     1      10.190   0.616   0.303  1.00  0.00           H  
HETATM   35  H5  UNL     1       8.491   0.923  -0.037  1.00  0.00           H  
HETATM   36  H6  UNL     1       9.873  -1.671   1.071  1.00  0.00           H  
HETATM   37  H7  UNL     1       8.051  -2.157   2.365  1.00  0.00           H  
HETATM   38  H8  UNL     1       6.662  -0.208   3.010  1.00  0.00           H  
HETATM   39  H9  UNL     1       5.820  -1.218   1.885  1.00  0.00           H  
HETATM   40  H10 UNL     1       7.055   1.637   1.463  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.574   1.983  -0.222  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.621   0.461  -0.473  1.00  0.00           H  
HETATM   43  H13 UNL     1       4.914  -0.024  -1.558  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.486  -2.072  -0.227  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.568  -3.058   0.753  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.058  -1.520   1.884  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.211  -0.247   0.581  1.00  0.00           H  
HETATM   48  H18 UNL     1       1.383  -1.858  -1.080  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.182  -3.072   0.247  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.002  -2.066  -0.051  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.282  -1.371   1.389  1.00  0.00           H  
HETATM   52  H22 UNL     1      -1.258   0.436   0.258  1.00  0.00           H  
HETATM   53  H23 UNL     1       0.476   0.623   0.407  1.00  0.00           H  
HETATM   54  H24 UNL     1       0.983   0.076  -1.864  1.00  0.00           H  
HETATM   55  H25 UNL     1      -0.093   1.456  -1.694  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.081  -1.298  -2.676  1.00  0.00           H  
HETATM   57  H27 UNL     1      -0.572   0.097  -3.620  1.00  0.00           H  
HETATM   58  H28 UNL     1      -2.389   1.420  -2.874  1.00  0.00           H  
HETATM   59  H29 UNL     1      -2.896  -0.138  -3.555  1.00  0.00           H  
HETATM   60  H30 UNL     1      -4.713  -0.358   0.455  1.00  0.00           H  
HETATM   61  H31 UNL     1      -3.327   1.634   1.230  1.00  0.00           H  
HETATM   62  H32 UNL     1      -4.727   2.706   0.726  1.00  0.00           H  
HETATM   63  H33 UNL     1      -6.365   1.961  -0.793  1.00  0.00           H  
HETATM   64  H34 UNL     1      -6.438   0.304  -1.353  1.00  0.00           H  
HETATM   65  H35 UNL     1      -8.135   2.634  -0.211  1.00  0.00           H  
HETATM   66  H36 UNL     1      -8.994   1.942   1.262  1.00  0.00           H  
HETATM   67  H37 UNL     1      -7.308   2.539   1.340  1.00  0.00           H  
HETATM   68  H38 UNL     1      -8.568  -0.915  -0.615  1.00  0.00           H  
HETATM   69  H39 UNL     1      -9.539   0.470  -0.068  1.00  0.00           H  
HETATM   70  H40 UNL     1      -8.558   0.689  -1.540  1.00  0.00           H  
HETATM   71  H41 UNL     1      -6.820  -0.908   1.479  1.00  0.00           H  
HETATM   72  H42 UNL     1      -8.577  -0.674   1.486  1.00  0.00           H  
HETATM   73  H43 UNL     1      -7.635   0.481   2.417  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4    4   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7    7   40
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   26   60
CONECT   22   23   61   62
CONECT   23   24   24   25
CONECT   26   27   63   64
CONECT   27   28   29   30
CONECT   28   65   66   67
CONECT   29   68   69   70
CONECT   30   71   72   73
END

HMDB0006319
     RDKit          3D
Alpha-linolenyl carnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    9.4722   -0.5279   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1899    0.1273    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   -0.9652    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416   -1.2379    1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876   -0.5339    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4517    0.7137    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    0.9060    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -0.0262   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5834   -1.4086   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283   -1.9893    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.3108    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -2.0048    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -1.3824    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3056    0.0355   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    0.3163   -1.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -0.1840   -2.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097    0.3249   -2.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    0.0450   -1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -1.0225   -0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    1.0098   -1.0091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    0.6563    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4596    1.6925    1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387    1.6293    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617    0.5415    3.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832    2.7986    3.2360 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3313    0.8914   -0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5167    0.6943    0.3308 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.0503    2.0199    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5939    0.1936   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5833   -0.1252    1.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5231    0.2408   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4256   -1.0859   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6949   -1.2896   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1904    0.6161    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4907    0.9230   -0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8725   -1.6706    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -2.1571    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6620   -0.2077    3.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8204   -1.2178    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0553    1.6368    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741    1.9825   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.4614   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141   -0.0241   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858   -2.0716   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683   -3.0585    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5195    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -0.2472    0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -1.8582   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816   -3.0715    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025   -2.0657   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -1.3715    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.4363    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759    0.6229    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    0.0764   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929    1.4562   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.2977   -2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.0972   -3.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    1.4199   -2.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -0.1380   -3.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.3580    0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.6340    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.7056    0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3653    1.9608   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4379    0.3036   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1353    2.6345   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9945    1.9421    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3082    2.5394    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5683   -0.9146   -0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5389    0.4696   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5577    0.6891   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8203   -0.9078    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5771   -0.6739    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6348    0.4811    2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  1
 22 61  1  0
 22 62  1  0
 26 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 30 73  1  0
M  CHG  2  25  -1  27   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Linolenyl carnitine	Generator
Α-linolenyl carnitine	Generator
(3S)-3-[(9Z,12Z,15Z)-Octadeca-9,12,15-trienoyloxy]-4-(trimethylazaniumyl)butanoic acid	HMDB

Chemical Formula

C₂₅H₄₃NO₄

Average Molecular Weight

421.622

Monoisotopic Molecular Weight

421.319208869

IUPAC Name

(3S)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h6-7,9-10,12-13,23H,5,8,11,14-22H2,1-4H3/b7-6-,10-9-,13-12-/t23-/m0/s1

InChI Key

WJCRATGUUISKDG-UHMZJXMFSA-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 salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006319)
Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0006319)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0006319)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.5e-05 g/L	ALOGPS
logP	1.35	ALOGPS
logP	1.84	ChemAxon
logS	-7.5	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	19	ChemAxon
Refractivity	149.63 m³·mol⁻¹	ChemAxon
Polarizability	50.04 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
DeepCCS	[M+H]+	230.361	30932474
DeepCCS	[M-H]-	227.101	30932474
DeepCCS	[M-2H]-	261.356	30932474
DeepCCS	[M+Na]+	237.858	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.88 minutes	32390414
Predicted by Siyang on May 30, 2022	21.8547 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	47.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3092.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	248.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	519.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	996.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	648.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	397.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2402.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	675.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2226.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	561.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	532.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	278.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	148.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpha-linolenyl carnitine	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	3482.9	Standard polar	33892256
Alpha-linolenyl carnitine	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	2608.3	Standard non polar	33892256
Alpha-linolenyl carnitine	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	2863.8	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 - Alpha-linolenyl carnitine 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 - Alpha-linolenyl carnitine 10V, Positive-QTOF	splash10-0h2f-1953800000-e6b9477dcd116b41475d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 20V, Positive-QTOF	splash10-0006-1920000000-2186fc8b7b7e1a3f4100	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 40V, Positive-QTOF	splash10-0006-4930000000-896b8fbf000c46bb7687	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 10V, Negative-QTOF	splash10-00di-1031900000-f32b57f41e39f3637d19	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 20V, Negative-QTOF	splash10-08or-1179400000-0f190d6f4cba56a454e4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 40V, Negative-QTOF	splash10-0a7l-5090000000-4f8caba1c3863fae2eed	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 10V, Positive-QTOF	splash10-00di-0000900000-5b8e47c72031be672844	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 20V, Positive-QTOF	splash10-0079-9000500000-538e3c7c8dad45a2f01e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-linolenyl carnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023886

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2614411

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156907992

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

LNLNCACRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. [PubMed:17508264 ]

Showing metabocard for Alpha-linolenyl carnitine (HMDB0006319)

MOL for HMDB0006319 (Alpha-linolenyl carnitine)

3D MOL for HMDB0006319 (Alpha-linolenyl carnitine)

3D SDF for HMDB0006319 (Alpha-linolenyl carnitine)

3D-SDF for HMDB0006319 (Alpha-linolenyl carnitine)

PDB for HMDB0006319 (Alpha-linolenyl carnitine)

3D PDB for HMDB0006319 (Alpha-linolenyl carnitine)

SMILES for HMDB0006319 (Alpha-linolenyl carnitine)

INCHI for HMDB0006319 (Alpha-linolenyl carnitine)

Structure for HMDB0006319 (Alpha-linolenyl carnitine)

3D Structure for HMDB0006319 (Alpha-linolenyl carnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra