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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:42:41 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062313

Secondary Accession Numbers

HMDB62313

Metabolite Identification

Common Name

1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate

Description

1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate is classified as a member of the 1-acylglycerol-3-phosphates. 1-acylglycerol-3-phosphates are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate is considered to be practically insoluble (in water) and acidic. 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate is a glycerophosphate lipid molecule

Structure

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


  Mrv1652303161704422D          

 38 37  0  0  1  0            999 V2000
    1.3776   -0.8546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.6796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -1.6796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -0.8546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    0.3829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513    2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2217    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
M  END

HMDB0062313
     RDKit          3D
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate
 72 71  0  0  0  0  0  0  0  0999 V2000
   -9.8041   -0.1758    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2199   -1.1863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3016   -2.1385   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0130   -1.8851    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264   -1.0199    1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7355    0.4188    1.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233    1.2430    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.9905    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122   -0.2955    1.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9380   -0.8932    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -0.4910   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.7696   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.7473   -1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.6932   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.8211   -2.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.7644   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504    0.4971   -1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    0.6122   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2199   -0.6318   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -0.4855   -0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.4362   -0.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    0.6169   -1.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    1.0350   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3446    1.3588    0.1304 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6502    2.3796    0.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6123    0.2127    1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2550   -0.8329    0.4021 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5415   -2.1068    1.4546 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1338   -1.7122    2.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4824    1.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2131   -2.3894    1.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6458   -0.4349    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9429   -0.1523    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5230    0.8669   -0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1126   -1.7553   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8019   -0.6998   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1434   -2.9893   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9276   -2.7904    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2915   -1.7122   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034   -2.9453    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627   -1.4349    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4697   -1.2887    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7509    0.9120    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0604    2.3432    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    1.5196    2.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    1.7156    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704   -0.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.9093    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405   -0.6844   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430   -1.2997   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.9750   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    2.6504   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    2.6458   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044    0.8974   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525    2.8470   -2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    1.0347   -3.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    2.6713   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    1.8362   -3.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.3379   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.3238   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    1.4759   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.8416   -2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.5099   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504   -0.8609    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525    0.3370   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    1.9937   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3564    1.8519   -0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    2.6455    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036   -0.1128    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3318    0.6344    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975   -3.7103    0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136   -1.5642    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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 23 65  1  0
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 26 69  1  0
 26 70  1  0
 30 71  1  0
 31 72  1  0
M  END


  Mrv1652303161704422D          

 38 37  0  0  1  0            999 V2000
    1.3776   -0.8546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.6796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -1.6796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -0.8546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    0.3829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513    2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2217    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062313

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h6-7,9-10,12-13,22,24H,2-5,8,11,14-21H2,1H3,(H2,26,27,28)/b7-6-,10-9-,13-12-/t22-/m1/s1

> <INCHI_KEY>
LZSKMXWVALYCLG-CSLWLMPESA-N

> <FORMULA>
C23H41O7P

> <MOLECULAR_WEIGHT>
460.548

> <EXACT_MASS>
460.258990658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.32197603468004

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
5.6509835383333336

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
126.73419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062313
     RDKit          3D
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate
 72 71  0  0  0  0  0  0  0  0999 V2000
   -9.8041   -0.1758    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2199   -1.1863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3016   -2.1385   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0130   -1.8851    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264   -1.0199    1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7355    0.4188    1.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233    1.2430    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.9905    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122   -0.2955    1.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9380   -0.8932    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -0.4910   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.7696   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.7473   -1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.6932   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.8211   -2.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.7644   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504    0.4971   -1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    0.6122   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2199   -0.6318   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -0.4855   -0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.4362   -0.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    0.6169   -1.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    1.0350   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3446    1.3588    0.1304 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6502    2.3796    0.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6123    0.2127    1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2550   -0.8329    0.4021 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5415   -2.1068    1.4546 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1338   -1.7122    2.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4824    1.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2131   -2.3894    1.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6458   -0.4349    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9429   -0.1523    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5230    0.8669   -0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1126   -1.7553   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8019   -0.6998   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1434   -2.9893   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9276   -2.7904    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2915   -1.7122   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034   -2.9453    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627   -1.4349    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4697   -1.2887    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7509    0.9120    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0604    2.3432    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    1.5196    2.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    1.7156    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704   -0.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.9093    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405   -0.6844   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430   -1.2997   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.9750   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    2.6504   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    2.6458   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044    0.8974   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525    2.8470   -2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    1.0347   -3.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    2.6713   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    1.8362   -3.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.3379   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.3238   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    1.4759   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.8416   -2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.5099   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504   -0.8609    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525    0.3370   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    1.9937   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3564    1.8519   -0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    2.6455    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036   -0.1128    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3318    0.6344    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975   -3.7103    0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136   -1.5642    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 26 69  1  0
 26 70  1  0
 30 71  1  0
 31 72  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0       2.572  -1.595   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       3.905  -0.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.905   0.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.572   1.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.572   3.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.238   3.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.238   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.239  -1.595   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       5.239  -3.135   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       6.573  -0.825   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.906  -1.595   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       7.906  -3.135   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       9.240  -0.825   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      10.574  -1.595   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       9.240   0.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.574   1.485   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      11.907   0.715   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      10.574   3.025   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      11.907   3.795   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       9.240   3.795   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.908   7.645   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      17.242   5.335   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      18.576   4.565   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      22.577   5.335   0.000  0.00  0.00           O+0
HETATM   35  P   UNK     0      23.910   6.105   0.000  0.00  0.00           P+0
HETATM   36  O   UNK     0      25.244   6.875   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      24.680   4.771   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      23.140   7.438   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   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   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   74    0
END

COMPND    HMDB0062313
HETATM    1  C1  UNL     1      -9.804  -0.176   0.158  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.220  -1.186  -0.768  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.302  -2.139  -0.153  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.013  -1.885   0.418  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.626  -1.020   1.528  1.00  0.00           C  
HETATM    6  C6  UNL     1      -6.736   0.419   1.479  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.723   1.243   1.535  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.307   0.990   1.656  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.712  -0.295   1.813  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.938  -0.893   0.956  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.460  -0.491  -0.348  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.860   0.770  -0.939  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.027   1.747  -1.269  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.578   1.693  -1.082  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.183   1.821  -2.395  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.664   1.764  -2.188  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.150   0.497  -1.562  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.666   0.612  -1.428  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.220  -0.632  -0.805  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.701  -0.485  -0.689  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.340  -1.436  -0.187  1.00  0.00           O  
HETATM   22  O2  UNL     1       6.332   0.617  -1.103  1.00  0.00           O  
HETATM   23  C21 UNL     1       7.632   1.035  -1.113  1.00  0.00           C  
HETATM   24  C22 UNL     1       8.345   1.359   0.130  1.00  0.00           C  
HETATM   25  O3  UNL     1       7.650   2.380   0.812  1.00  0.00           O  
HETATM   26  C23 UNL     1       8.612   0.213   1.040  1.00  0.00           C  
HETATM   27  O4  UNL     1       9.255  -0.833   0.402  1.00  0.00           O  
HETATM   28  P1  UNL     1       9.541  -2.107   1.455  1.00  0.00           P  
HETATM   29  O5  UNL     1       9.134  -1.712   2.865  1.00  0.00           O  
HETATM   30  O6  UNL     1       8.699  -3.482   1.002  1.00  0.00           O  
HETATM   31  O7  UNL     1      11.213  -2.389   1.502  1.00  0.00           O  
HETATM   32  H1  UNL     1      -9.646  -0.435   1.224  1.00  0.00           H  
HETATM   33  H2  UNL     1     -10.943  -0.152   0.068  1.00  0.00           H  
HETATM   34  H3  UNL     1      -9.523   0.867  -0.089  1.00  0.00           H  
HETATM   35  H4  UNL     1     -10.113  -1.755  -1.208  1.00  0.00           H  
HETATM   36  H5  UNL     1      -8.802  -0.700  -1.700  1.00  0.00           H  
HETATM   37  H6  UNL     1      -8.143  -2.989  -0.948  1.00  0.00           H  
HETATM   38  H7  UNL     1      -8.928  -2.790   0.607  1.00  0.00           H  
HETATM   39  H8  UNL     1      -6.291  -1.712  -0.484  1.00  0.00           H  
HETATM   40  H9  UNL     1      -6.603  -2.945   0.728  1.00  0.00           H  
HETATM   41  H10 UNL     1      -5.763  -1.435   2.125  1.00  0.00           H  
HETATM   42  H11 UNL     1      -7.470  -1.289   2.346  1.00  0.00           H  
HETATM   43  H12 UNL     1      -7.751   0.912   1.422  1.00  0.00           H  
HETATM   44  H13 UNL     1      -6.060   2.343   1.475  1.00  0.00           H  
HETATM   45  H14 UNL     1      -4.051   1.520   2.705  1.00  0.00           H  
HETATM   46  H15 UNL     1      -3.704   1.716   1.024  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.870  -0.824   2.784  1.00  0.00           H  
HETATM   48  H17 UNL     1      -2.584  -1.909   1.305  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.341  -0.684  -0.439  1.00  0.00           H  
HETATM   50  H19 UNL     1      -2.843  -1.300  -1.086  1.00  0.00           H  
HETATM   51  H20 UNL     1      -3.932   0.975  -1.167  1.00  0.00           H  
HETATM   52  H21 UNL     1      -2.476   2.650  -1.711  1.00  0.00           H  
HETATM   53  H22 UNL     1      -0.284   2.646  -0.524  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.204   0.897  -0.430  1.00  0.00           H  
HETATM   55  H24 UNL     1      -0.053   2.847  -2.775  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.105   1.035  -3.103  1.00  0.00           H  
HETATM   57  H26 UNL     1       2.047   2.671  -1.637  1.00  0.00           H  
HETATM   58  H27 UNL     1       2.136   1.836  -3.196  1.00  0.00           H  
HETATM   59  H28 UNL     1       1.934  -0.338  -2.250  1.00  0.00           H  
HETATM   60  H29 UNL     1       1.749   0.324  -0.545  1.00  0.00           H  
HETATM   61  H30 UNL     1       3.914   1.476  -0.762  1.00  0.00           H  
HETATM   62  H31 UNL     1       4.135   0.842  -2.405  1.00  0.00           H  
HETATM   63  H32 UNL     1       4.053  -1.510  -1.470  1.00  0.00           H  
HETATM   64  H33 UNL     1       3.750  -0.861   0.155  1.00  0.00           H  
HETATM   65  H34 UNL     1       8.253   0.337  -1.767  1.00  0.00           H  
HETATM   66  H35 UNL     1       7.650   1.994  -1.741  1.00  0.00           H  
HETATM   67  H36 UNL     1       9.356   1.852  -0.126  1.00  0.00           H  
HETATM   68  H37 UNL     1       6.830   2.646   0.305  1.00  0.00           H  
HETATM   69  H38 UNL     1       7.704  -0.113   1.537  1.00  0.00           H  
HETATM   70  H39 UNL     1       9.332   0.634   1.835  1.00  0.00           H  
HETATM   71  H40 UNL     1       8.898  -3.710   0.070  1.00  0.00           H  
HETATM   72  H41 UNL     1      11.714  -1.564   1.274  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7    7   43
CONECT    7    8   44
CONECT    8    9   45   46
CONECT    9   10   10   47
CONECT   10   11   48
CONECT   11   12   49   50
CONECT   12   13   13   51
CONECT   13   14   52
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   57   58
CONECT   17   18   59   60
CONECT   18   19   61   62
CONECT   19   20   63   64
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   65   66
CONECT   24   25   26   67
CONECT   25   68
CONECT   26   27   69   70
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   71
CONECT   31   72
END

HMDB0062313
     RDKit          3D
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate
 72 71  0  0  0  0  0  0  0  0999 V2000
   -9.8041   -0.1758    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2199   -1.1863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3016   -2.1385   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0130   -1.8851    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264   -1.0199    1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7355    0.4188    1.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233    1.2430    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.9905    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122   -0.2955    1.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9380   -0.8932    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -0.4910   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.7696   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.7473   -1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.6932   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.8211   -2.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    1.7644   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504    0.4971   -1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    0.6122   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2199   -0.6318   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -0.4855   -0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.4362   -0.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    0.6169   -1.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    1.0350   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3446    1.3588    0.1304 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6502    2.3796    0.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6123    0.2127    1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2550   -0.8329    0.4021 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5415   -2.1068    1.4546 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1338   -1.7122    2.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4824    1.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2131   -2.3894    1.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6458   -0.4349    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9429   -0.1523    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5230    0.8669   -0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1126   -1.7553   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8019   -0.6998   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1434   -2.9893   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9276   -2.7904    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2915   -1.7122   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034   -2.9453    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627   -1.4349    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4697   -1.2887    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7509    0.9120    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0604    2.3432    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    1.5196    2.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    1.7156    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704   -0.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.9093    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405   -0.6844   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430   -1.2997   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.9750   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    2.6504   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    2.6458   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044    0.8974   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525    2.8470   -2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    1.0347   -3.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    2.6713   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    1.8362   -3.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.3379   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.3238   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    1.4759   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.8416   -2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.5099   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504   -0.8609    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525    0.3370   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    1.9937   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3564    1.8519   -0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    2.6455    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036   -0.1128    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3318    0.6344    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975   -3.7103    0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136   -1.5642    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 26 69  1  0
 26 70  1  0
 30 71  1  0
 31 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(8Z,11Z,14Z-Eicosatrienoyl)-glycero-3-phosphoric acid	Generator

Chemical Formula

C₂₃H₄₁O₇P

Average Molecular Weight

460.548

Monoisotopic Molecular Weight

460.258990658

IUPAC Name

[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C23H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h6-7,9-10,12-13,22,24H,2-5,8,11,14-21H2,1H3,(H2,26,27,28)/b7-6-,10-9-,13-12-/t22-/m1/s1

InChI Key

LZSKMXWVALYCLG-CSLWLMPESA-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

Monoacylglycerophosphates (LMGP10050028 )

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	0.0019 g/l	ALOGPS
LogP	5.13	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.13	ALOGPS
logP	5.65	ChemAxon
logS	-5.4	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	21	ChemAxon
Refractivity	126.73 m³·mol⁻¹	ChemAxon
Polarizability	51.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	221.206	31661259
DarkChem	[M-H]-	220.538	31661259
DeepCCS	[M+H]+	202.706	30932474
DeepCCS	[M-H]-	200.604	30932474
DeepCCS	[M-2H]-	233.845	30932474
DeepCCS	[M+Na]+	208.447	30932474
AllCCS	[M+H]+	216.4	32859911
AllCCS	[M+H-H2O]+	214.5	32859911
AllCCS	[M+NH4]+	218.2	32859911
AllCCS	[M+Na]+	218.7	32859911
AllCCS	[M-H]-	212.2	32859911
AllCCS	[M+Na-2H]-	215.4	32859911
AllCCS	[M+HCOO]-	219.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	4297.0	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	2942.7	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	3473.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C	3484.5	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C	3452.0	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3466.5	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3186.5	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3999.6	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3438.3	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3194.3	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3754.5	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3449.9	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3206.0	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3444.3	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3721.4	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3665.2	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3910.0	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3495.7	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4015.4	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3880.0	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3474.9	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3845.5	Standard polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=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	4099.2	Semi standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=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	3598.3	Standard non polar	33892256
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=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	3581.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-01p2-9350000000-b0e6c953e4bf2e56ac2e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-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-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 10V, Negative-QTOF	splash10-0a4i-0000900000-9ca2a2af5e5fc3a4e69f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 20V, Negative-QTOF	splash10-0a4i-0000900000-9ca2a2af5e5fc3a4e69f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 40V, Negative-QTOF	splash10-0pb9-2905600000-561b7a040f4d1c93af57	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 10V, Positive-QTOF	splash10-03di-0000900000-0a6b37d058721276c7d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 20V, Positive-QTOF	splash10-03di-0000900000-0a6b37d058721276c7d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate 40V, Positive-QTOF	splash10-00du-0950700000-206c097451145463db3e	2021-09-24	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

52929761

PDB ID

Not Available

ChEBI ID

Not Available

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-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate (HMDB0062313)

MOL for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

3D MOL for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

3D SDF for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

3D-SDF for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

PDB for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

3D PDB for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

SMILES for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

INCHI for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

Structure for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

3D Structure for HMDB0062313 (1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra