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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:43:28 UTC

Update Date

2022-03-07 03:17:53 UTC

HMDB ID

HMDB0062320

Secondary Accession Numbers

HMDB62320

Metabolite Identification

Common Name

1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate

Description

1-linolenoyl-sn-glycero-3-phosphate, also known as PA(18:3(9Z,12Z,15Z)/0:0), belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. 1-linolenoyl-sn-glycero-3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv1572008171515212D          

 36 35  0  0  1  0            999 V2000
    0.2952    5.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    5.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955    4.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936    4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    3.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    2.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    2.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768    2.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    3.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786    4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    4.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657    3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584    4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8529    3.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0326    3.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4197    3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271    2.8578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6455    3.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289    2.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    4.5739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5995    2.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0356    1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5780    3.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2400    3.2011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0142    2.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068    2.7434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    5.4892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863    3.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    2.5146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010    1.3705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860    1.0273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    1.4850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8252    3.6587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 20 22  1  1  0  0  0
 23 21  2  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 28  1  0  0  0  0
 30  3  1  0  0  0  0
 31  4  1  0  0  0  0
 32  6  1  0  0  0  0
 33  7  1  0  0  0  0
 34  9  1  0  0  0  0
 35 10  1  0  0  0  0
 20 36  1  1  0  0  0
M  END

HMDB0062320
     RDKit          3D
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate
 66 65  0  0  0  0  0  0  0  0999 V2000
   10.2660   -0.3632    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5999   -0.5176    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7365   -0.4064   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4702   -0.1490   -0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6071    0.0994    0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0517    1.4816    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686    1.6597    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7564    0.5765    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    0.5948   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7614    0.7795   -1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    1.0035   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8063   -0.1166   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -0.0977   -1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.1595   -1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575   -1.0558   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7816    0.2517   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.4020    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8864   -0.6225    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467   -1.3831   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9133   -0.7279    1.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -1.6849    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7142   -1.4655   -0.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7294   -2.4180   -0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.1104    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2747   -0.0844    1.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0134    1.4348    1.1476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.7182    2.2305   -0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4018    2.3293    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6956    1.2679    1.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9857    0.6847    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2540   -0.4656    2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6483   -1.1206    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014    0.0752    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740   -1.5857    0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2230   -0.5702   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657   -0.1051   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7134   -0.6111    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0152    0.0072    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045    2.3429    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    2.6707   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -0.4014    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    0.9354    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6873    0.4272   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.7631   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    1.9317   -0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2800    1.1780    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -1.1126   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    0.0216    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7212   -0.2276   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272    0.8937   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900   -2.1883   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4873   -1.0870   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068   -1.0986    0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6897   -1.9536   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856    1.1157   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    0.2817   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4172    0.2429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737    1.4179    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6093   -1.5877    2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5161   -2.7261    1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0917   -1.4741   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6326   -2.8778   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0271    0.0184   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6284    0.6898    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6807    3.2701    2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9958    0.4767    0.8252 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 24 63  1  0
 24 64  1  0
 28 65  1  0
 29 66  1  0
M  END


  Mrv1572008171515212D          

 36 35  0  0  1  0            999 V2000
    0.2952    5.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    5.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955    4.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936    4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    3.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    2.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    2.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768    2.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    3.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786    4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    4.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657    3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584    4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8529    3.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0326    3.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4197    3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271    2.8578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6455    3.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289    2.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    4.5739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5995    2.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0356    1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5780    3.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2400    3.2011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0142    2.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068    2.7434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    5.4892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863    3.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    2.5146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010    1.3705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860    1.0273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    1.4850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8252    3.6587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 20 22  1  1  0  0  0
 23 21  2  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 28  1  0  0  0  0
 30  3  1  0  0  0  0
 31  4  1  0  0  0  0
 32  6  1  0  0  0  0
 33  7  1  0  0  0  0
 34  9  1  0  0  0  0
 35 10  1  0  0  0  0
 20 36  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0062320

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h3-4,6-7,9-10,20,22H,2,5,8,11-19H2,1H3,(H2,24,25,26)/b4-3-,7-6-,10-9-/t20-/m1/s1

> <INCHI_KEY>
DVNZKWQUAXJYGB-LVTNFWOSSA-N

> <FORMULA>
C21H37O7P

> <MOLECULAR_WEIGHT>
432.494

> <EXACT_MASS>
432.227690529

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.688963655936796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.761846208333333

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556444

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
117.53219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062320
     RDKit          3D
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate
 66 65  0  0  0  0  0  0  0  0999 V2000
   10.2660   -0.3632    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5999   -0.5176    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7365   -0.4064   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4702   -0.1490   -0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6071    0.0994    0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0517    1.4816    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686    1.6597    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7564    0.5765    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    0.5948   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7614    0.7795   -1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    1.0035   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8063   -0.1166   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -0.0977   -1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.1595   -1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575   -1.0558   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7816    0.2517   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.4020    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8864   -0.6225    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467   -1.3831   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9133   -0.7279    1.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -1.6849    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7142   -1.4655   -0.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7294   -2.4180   -0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.1104    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2747   -0.0844    1.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0134    1.4348    1.1476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.7182    2.2305   -0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4018    2.3293    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6956    1.2679    1.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9857    0.6847    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2540   -0.4656    2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6483   -1.1206    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014    0.0752    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740   -1.5857    0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2230   -0.5702   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657   -0.1051   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7134   -0.6111    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0152    0.0072    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045    2.3429    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    2.6707   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -0.4014    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    0.9354    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6873    0.4272   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.7631   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    1.9317   -0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2800    1.1780    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -1.1126   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    0.0216    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7212   -0.2276   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272    0.8937   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900   -2.1883   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4873   -1.0870   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068   -1.0986    0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6897   -1.9536   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856    1.1157   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    0.2817   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4172    0.2429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737    1.4179    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6093   -1.5877    2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5161   -2.7261    1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0917   -1.4741   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6326   -2.8778   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0271    0.0184   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6284    0.6898    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6807    3.2701    2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9958    0.4767    0.8252 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 24 63  1  0
 24 64  1  0
 28 65  1  0
 29 66  1  0
M  END

HEADER    PROTEIN                                 17-AUG-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-AUG-15         0                                  
HETATM    1  C   UNK     0       0.551  11.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.181   9.606   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.298   9.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.668   7.684   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.559   6.616   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.928   5.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.181   4.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.661   4.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.771   3.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.250   3.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.510   6.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.880   7.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.360   8.324   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.469   7.257   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.949   7.684   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.059   6.616   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.128   6.402   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.717   5.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.237   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.538   7.043   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.867   3.840   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.908   8.538   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      19.786   5.548   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.733   3.641   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      17.879   6.601   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.648   5.975   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.827   4.694   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      18.306   5.121   0.000  0.00  0.00           P+0
HETATM   30  H   UNK     0      -2.408  10.247   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.148   7.257   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.408   4.694   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.189   2.558   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.401   1.918   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.360   2.772   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      14.607   6.830   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   21                                                       
CONECT   18   20   27                                                       
CONECT   19   20   28                                                       
CONECT   20   18   19   22   36                                             
CONECT   21   17   23   27                                                  
CONECT   22   20                                                            
CONECT   23   21                                                            
CONECT   24   29                                                            
CONECT   25   29                                                            
CONECT   26   29                                                            
CONECT   27   18   21                                                       
CONECT   28   19   29                                                       
CONECT   29   24   25   26   28                                             
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

COMPND    HMDB0062320
HETATM    1  C1  UNL     1      10.266  -0.363   1.700  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.600  -0.518   0.289  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.737  -0.406  -0.833  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.470  -0.149  -0.908  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.607   0.099   0.270  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.052   1.482   0.116  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.769   1.660   0.067  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.756   0.576   0.157  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.031   0.595  -1.138  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.761   0.779  -1.329  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.849   1.003  -0.222  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.806  -0.117  -0.204  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.038  -0.098  -1.494  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.018  -1.160  -1.562  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.057  -1.056  -0.473  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.782   0.252  -0.531  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.830   0.402   0.528  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.886  -0.623   0.360  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.847  -1.383  -0.628  1.00  0.00           O  
HETATM   20  O2  UNL     1      -5.913  -0.728   1.306  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.920  -1.685   1.163  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.714  -1.466  -0.082  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.729  -2.418  -0.238  1.00  0.00           O  
HETATM   24  C21 UNL     1      -8.399  -0.110   0.001  1.00  0.00           C  
HETATM   25  O4  UNL     1      -9.275  -0.084   1.094  1.00  0.00           O  
HETATM   26  P1  UNL     1     -10.013   1.435   1.148  1.00  0.00           P  
HETATM   27  O5  UNL     1      -9.718   2.231  -0.114  1.00  0.00           O  
HETATM   28  O6  UNL     1      -9.402   2.329   2.464  1.00  0.00           O  
HETATM   29  O7  UNL     1     -11.696   1.268   1.359  1.00  0.00           O  
HETATM   30  H1  UNL     1       9.986   0.685   1.956  1.00  0.00           H  
HETATM   31  H2  UNL     1      11.254  -0.466   2.336  1.00  0.00           H  
HETATM   32  H3  UNL     1       9.648  -1.121   2.185  1.00  0.00           H  
HETATM   33  H4  UNL     1      11.601   0.075   0.077  1.00  0.00           H  
HETATM   34  H5  UNL     1      11.074  -1.586   0.212  1.00  0.00           H  
HETATM   35  H6  UNL     1      10.223  -0.570  -1.883  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.966  -0.105  -1.926  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.713  -0.611   0.181  1.00  0.00           H  
HETATM   38  H9  UNL     1       8.015   0.007   1.240  1.00  0.00           H  
HETATM   39  H10 UNL     1       7.704   2.343   0.045  1.00  0.00           H  
HETATM   40  H11 UNL     1       5.350   2.671  -0.050  1.00  0.00           H  
HETATM   41  H12 UNL     1       5.070  -0.401   0.472  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.005   0.935   0.947  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.687   0.427  -2.019  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.430   0.763  -2.389  1.00  0.00           H  
HETATM   45  H16 UNL     1       1.230   1.932  -0.449  1.00  0.00           H  
HETATM   46  H17 UNL     1       2.280   1.178   0.740  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.299  -1.113  -0.095  1.00  0.00           H  
HETATM   48  H19 UNL     1       0.164   0.022   0.681  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.721  -0.228  -2.378  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.427   0.894  -1.657  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.590  -2.188  -1.485  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.487  -1.087  -2.572  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.507  -1.099   0.502  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.690  -1.954  -0.570  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.086   1.116  -0.564  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.304   0.282  -1.525  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.417   0.243   1.553  1.00  0.00           H  
HETATM   58  H29 UNL     1      -4.274   1.418   0.426  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.609  -1.588   2.033  1.00  0.00           H  
HETATM   60  H31 UNL     1      -6.516  -2.726   1.122  1.00  0.00           H  
HETATM   61  H32 UNL     1      -7.092  -1.474  -0.986  1.00  0.00           H  
HETATM   62  H33 UNL     1      -8.633  -2.878  -1.102  1.00  0.00           H  
HETATM   63  H34 UNL     1      -9.027   0.018  -0.905  1.00  0.00           H  
HETATM   64  H35 UNL     1      -7.628   0.690   0.067  1.00  0.00           H  
HETATM   65  H36 UNL     1      -9.681   3.270   2.385  1.00  0.00           H  
HETATM   66  H37 UNL     1     -11.996   0.477   0.825  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    4   35
CONECT    4    5   36
CONECT    5    6   37   38
CONECT    6    7    7   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   47   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   53   54
CONECT   16   17   55   56
CONECT   17   18   57   58
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   59   60
CONECT   22   23   24   61
CONECT   23   62
CONECT   24   25   63   64
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   65
CONECT   29   66
END

HMDB0062320
     RDKit          3D
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate
 66 65  0  0  0  0  0  0  0  0999 V2000
   10.2660   -0.3632    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5999   -0.5176    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7365   -0.4064   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4702   -0.1490   -0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6071    0.0994    0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0517    1.4816    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686    1.6597    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7564    0.5765    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    0.5948   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7614    0.7795   -1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    1.0035   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8063   -0.1166   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -0.0977   -1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.1595   -1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575   -1.0558   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7816    0.2517   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.4020    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8864   -0.6225    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467   -1.3831   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9133   -0.7279    1.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -1.6849    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7142   -1.4655   -0.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7294   -2.4180   -0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.1104    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2747   -0.0844    1.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0134    1.4348    1.1476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.7182    2.2305   -0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4018    2.3293    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6956    1.2679    1.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9857    0.6847    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2540   -0.4656    2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6483   -1.1206    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014    0.0752    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740   -1.5857    0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2230   -0.5702   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657   -0.1051   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7134   -0.6111    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0152    0.0072    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045    2.3429    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    2.6707   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -0.4014    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    0.9354    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6873    0.4272   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.7631   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    1.9317   -0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2800    1.1780    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -1.1126   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    0.0216    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7212   -0.2276   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272    0.8937   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900   -2.1883   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4873   -1.0870   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068   -1.0986    0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6897   -1.9536   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856    1.1157   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    0.2817   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4172    0.2429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737    1.4179    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6093   -1.5877    2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5161   -2.7261    1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0917   -1.4741   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6326   -2.8778   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0271    0.0184   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6284    0.6898    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6807    3.2701    2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9958    0.4767    0.8252 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 24 63  1  0
 24 64  1  0
 28 65  1  0
 29 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(9Z,12Z,15Z)-Octadecatrienoyl-sn-glycero-3-phosphate	ChEBI
1-(9Z,12Z,15Z-Octadecatrienoyl)-glycero-3-phosphate	ChEBI
PA(18:3(9Z,12Z,15Z)/0:0)	ChEBI
1-(9Z,12Z,15Z)-Octadecatrienoyl-sn-glycero-3-phosphoric acid	Generator
1-(9Z,12Z,15Z-Octadecatrienoyl)-glycero-3-phosphoric acid	Generator
1-Linolenoyl-sn-glycero-3-phosphoric acid	Generator

Chemical Formula

C₂₁H₃₇O₇P

Average Molecular Weight

432.494

Monoisotopic Molecular Weight

432.227690529

IUPAC Name

[(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h3-4,6-7,9-10,20,22H,2,5,8,11-19H2,1H3,(H2,24,25,26)/b4-3-,7-6-,10-9-/t20-/m1/s1

InChI Key

DVNZKWQUAXJYGB-LVTNFWOSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate (CHEBI:74831 )
Monoacylglycerophosphates (LMGP10050035 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.004 g/l	ALOGPS
LogP	4.32	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.32	ALOGPS
logP	4.76	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	117.53 m³·mol⁻¹	ChemAxon
Polarizability	46.69 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
DarkChem	[M+H]+	210.689	31661259
DarkChem	[M-H]-	208.867	31661259
DeepCCS	[M+H]+	202.664	30932474
DeepCCS	[M-H]-	200.269	30932474
DeepCCS	[M-2H]-	233.3	30932474
DeepCCS	[M+Na]+	208.577	30932474
AllCCS	[M+H]+	208.6	32859911
AllCCS	[M+H-H2O]+	206.6	32859911
AllCCS	[M+NH4]+	210.6	32859911
AllCCS	[M+Na]+	211.1	32859911
AllCCS	[M-H]-	203.9	32859911
AllCCS	[M+Na-2H]-	206.6	32859911
AllCCS	[M+HCOO]-	209.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	4327.4	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	2761.8	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	3263.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C	3301.9	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C	3273.7	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3291.7	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3031.3	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3837.6	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3266.7	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3038.0	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3602.6	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3269.6	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3054.5	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3310.6	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3532.1	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3482.1	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3728.9	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3341.1	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3864.3	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3702.2	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3317.6	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3702.4	Standard polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3923.8	Semi standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3451.4	Standard non polar	33892256
1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3452.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-03ds-9440000000-bbdd6e79093026413d38	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 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 - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 10V, Negative-QTOF	splash10-001i-0000900000-6fe5a0721925d7402523	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 20V, Negative-QTOF	splash10-001i-0000900000-6fe5a0721925d7402523	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 40V, Negative-QTOF	splash10-0ugi-2950600000-3b4c6c0770f021a90a0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 10V, Positive-QTOF	splash10-001i-0000900000-108d02e82a2642c9aead	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 20V, Positive-QTOF	splash10-001i-0000900000-108d02e82a2642c9aead	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate 40V, Positive-QTOF	splash10-02mi-0950700000-e34f2b7be7c16d75d15a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

74831

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate (HMDB0062320)

MOL for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

3D MOL for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

3D SDF for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

3D-SDF for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

PDB for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

3D PDB for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

SMILES for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

INCHI for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

Structure for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

3D Structure for HMDB0062320 (1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra