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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 21:59:02 UTC

Update Date

2022-11-30 19:59:01 UTC

HMDB ID

HMDB0272658

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))

Description

PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) is an oxidized phosphoglycerophosphate (PGP). Oxidized phosphoglycerophosphates are glycerophospholipids in which a phosphoglycerol moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphoglycerophosphates belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphoglycerophosphates can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)), in particular, consists of one chain of one 11Z-octadecenoyl at the C-1 position and one chain of 9,10-hydroxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PGPs can be synthesized via three different routes. In one route, the oxidized PGP is synthetized de novo following the same mechanisms as for PGPs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PGP backbone, mainely through the action of LOX (PMID: 33329396 ).

Structure

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

PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))
  Mrv1652309122123592D          

 61 60  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    1.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6134    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7177    0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.8108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156    1.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.8990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6518   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2225   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9366    0.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1898   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9039   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6180   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3321   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0462   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7604   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 19  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8 16  1  0  0  0  0
  8 15  1  6  0  0  0
  9  8  1  0  0  0  0
  9 14  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 19 18  1  0  0  0  0
 21 41  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  END

HMDB0272658
     RDKit          3D
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))
139138  0  0  0  0  0  0  0  0999 V2000
   -6.2969   -4.1969   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2132   -2.7196    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309   -2.3085    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546   -0.8293    0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7118   -0.2783    1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -0.6229    0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    0.1813    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8907    1.6313    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    2.3181   -0.9016 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.7954   -1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896    2.6510   -1.7413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0057    3.2222   -0.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457    1.6164   -2.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453    0.9554   -3.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288    0.0378   -4.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771   -1.0965   -4.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579   -2.1835   -3.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -3.1854   -3.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -4.3668   -2.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -4.0260   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300   -2.9339   -0.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732   -4.9629    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -4.6360    1.4740 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5070   -4.3364    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696   -3.2729    1.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -2.6537    1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -3.0550    2.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7312   -1.5215    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269   -0.1859    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726    0.8847    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226    2.2629    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480    3.2907   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421    4.6919    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2443    5.6982   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500    5.6079   -1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008    6.6618   -2.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444    8.0011   -2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9960    8.9174   -2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    8.7062   -4.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    8.9101   -3.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461    8.6960   -5.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    8.8809   -4.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196    8.6513   -6.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260    9.6394   -7.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -5.7769    2.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264   -5.5225    3.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217   -6.9160    4.2957 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0791   -7.8081    3.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -7.7177    4.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3114   -6.4270    5.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9249   -7.5334    6.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965   -7.0998    7.2975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4242   -8.2320    7.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -6.3798    8.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -7.2141    8.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -6.3530   10.0798 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9575   -6.2010   11.3401 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595   -7.2328   10.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -4.8150    9.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6479   -4.7926    0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0261   -4.3349   -1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3149   -4.5877   -0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2841   -2.2120   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0758   -2.4242    0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0749   -2.5562    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8610   -2.8593    1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7992   -0.5762    1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591   -0.2722    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9124    0.7362    1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6617   -0.8628    2.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.7157    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8522   -0.2775   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574    1.9610    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745    2.0370    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5540    3.3563   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9931    1.8557   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    3.5204   -2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    2.5020   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.8922   -1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5053    2.1616   -3.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599    0.4265   -3.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7785    1.7514   -4.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372    0.6036   -5.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -0.3612   -5.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984   -0.8555   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -1.6699   -5.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2200   -2.6749   -3.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684   -1.7846   -2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -3.4202   -4.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215   -2.6117   -2.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985   -4.8922   -2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -5.0446   -2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542   -3.7135    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -5.2544    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -4.1039    3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -1.6001    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948   -1.6149   -0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122   -0.0948    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190   -0.0489    2.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953    0.7037    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093    0.7475   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    2.4236    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5188    2.3468    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    3.1561   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    3.1786   -0.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513    4.7985    0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    4.8700    1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    6.7389   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    5.5953   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    4.6040   -2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    5.7356   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0194    6.4889   -3.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4818    6.4253   -3.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084    8.2619   -1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9137    9.9405   -2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    7.8339   -4.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443    9.5893   -4.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    8.2191   -3.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    9.9652   -3.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    7.6642   -5.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    9.4009   -5.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877    9.8691   -4.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    8.0812   -4.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203    8.6839   -6.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542    7.6372   -6.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   10.6202   -6.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398    9.3213   -7.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408    9.6878   -8.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591   -6.7172    2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -6.0858    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045   -7.3755    5.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -8.1956    6.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437   -8.1493    5.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6150   -6.4478    6.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1352   -7.9029    8.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896   -5.5087    7.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -6.0304    9.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -7.6353    9.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -4.7753    8.5663 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  1  0
  9 11  1  0
 11 12  1  0
 11 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  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
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 23 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  2  0
 47 49  1  0
 47 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  1  0
 54 55  1  0
 55 56  1  0
 56 57  2  0
 56 58  1  0
 56 59  1  0
  1 60  1  0
  1 61  1  0
  1 62  1  0
  2 63  1  0
  2 64  1  0
  3 65  1  0
  3 66  1  0
  4 67  1  0
  4 68  1  0
  5 69  1  0
  5 70  1  0
  6 71  1  0
  7 72  1  0
  8 73  1  0
  8 74  1  0
  9 75  1  1
 10 76  1  0
 11 77  1  6
 12 78  1  0
 13 79  1  0
 13 80  1  0
 14 81  1  0
 14 82  1  0
 15 83  1  0
 15 84  1  0
 16 85  1  0
 16 86  1  0
 17 87  1  0
 17 88  1  0
 18 89  1  0
 18 90  1  0
 19 91  1  0
 19 92  1  0
 23 93  1  6
 24 94  1  0
 24 95  1  0
 28 96  1  0
 28 97  1  0
 29 98  1  0
 29 99  1  0
 30100  1  0
 30101  1  0
 31102  1  0
 31103  1  0
 32104  1  0
 32105  1  0
 33106  1  0
 33107  1  0
 34108  1  0
 34109  1  0
 35110  1  0
 35111  1  0
 36112  1  0
 36113  1  0
 37114  1  0
 38115  1  0
 39116  1  0
 39117  1  0
 40118  1  0
 40119  1  0
 41120  1  0
 41121  1  0
 42122  1  0
 42123  1  0
 43124  1  0
 43125  1  0
 44126  1  0
 44127  1  0
 44128  1  0
 45129  1  0
 45130  1  0
 49131  1  0
 51132  1  0
 51133  1  0
 52134  1  6
 53135  1  0
 54136  1  0
 54137  1  0
 58138  1  0
 59139  1  0
M  END

PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))
  Mrv1652309122123592D          

 61 60  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    1.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6134    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7177    0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.8108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156    1.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.8990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6518   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2225   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9366    0.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1898   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9039   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6180   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3321   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0462   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7604   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 19  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8 16  1  0  0  0  0
  8 15  1  6  0  0  0
  9  8  1  0  0  0  0
  9 14  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 19 18  1  0  0  0  0
 21 41  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0272658

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C42H80O15P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-23-27-31-41(46)53-35-38(36-56-59(51,52)55-34-37(43)33-54-58(48,49)50)57-42(47)32-28-24-20-22-26-30-40(45)39(44)29-25-21-10-8-6-4-2/h12-13,21,25,37-40,43-45H,3-11,14-20,22-24,26-36H2,1-2H3,(H,51,52)(H2,48,49,50)/b13-12-,25-21-/t37-,38+,39-,40-/m0/s1

> <INCHI_KEY>
LEKKVGFOGZWYCI-ITOGZDHKSA-N

> <FORMULA>
C42H80O15P2

> <MOLECULAR_WEIGHT>
887.035

> <EXACT_MASS>
886.497245872

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
99.67430318888121

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
6.02

> <JCHEM_LOGP>
9.406294700666667

> <ALOGPS_LOGS>
-5.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.040206143698428

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3548792964149925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148519607080269

> <JCHEM_POLAR_SURFACE_AREA>
235.80999999999997

> <JCHEM_REFRACTIVITY>
229.85000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0272658
     RDKit          3D
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))
139138  0  0  0  0  0  0  0  0999 V2000
   -6.2969   -4.1969   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2132   -2.7196    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309   -2.3085    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546   -0.8293    0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.545   2.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.878   1.441   0.000  0.00  0.00           C+0
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HETATM   25  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -17.215  -2.873   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -18.548   0.778   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -22.754  -0.662   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -24.087  -1.433   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -25.420  -0.662   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -26.753  -1.433   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -28.086  -0.662   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -29.419  -1.433   0.000  0.00  0.00           C+0
CONECT    1   22   17                                                       
CONECT    2   19    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   16   15    9                                             
CONECT    9    8   14                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   11                                                       
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    1   18                                                       
CONECT   18   17   20   21   19                                             
CONECT   19    2   18                                                       
CONECT   20   18                                                            
CONECT   21   18   41                                                       
CONECT   22    1   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   21   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  120    0
END

COMPND    HMDB0272658
HETATM    1  C1  UNL     1      -6.297  -4.197  -0.184  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.213  -2.720   0.061  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.931  -2.308   0.760  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.955  -0.829   0.948  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.712  -0.278   1.647  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.532  -0.623   0.869  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.671   0.181   0.284  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.891   1.631   0.403  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.123   2.318  -0.902  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.215   1.795  -1.597  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.990   2.651  -1.741  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.006   3.222  -0.890  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.346   1.616  -2.615  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.245   0.955  -3.580  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.629   0.038  -4.550  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.177  -1.096  -4.164  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.458  -2.183  -3.286  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.659  -3.185  -3.132  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.399  -4.367  -2.310  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.120  -4.026  -0.903  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.330  -2.934  -0.521  1.00  0.00           O  
HETATM   22  O4  UNL     1       0.373  -4.963   0.111  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.109  -4.636   1.474  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.507  -4.336   2.131  1.00  0.00           C  
HETATM   25  O5  UNL     1       2.070  -3.273   1.422  1.00  0.00           O  
HETATM   26  C21 UNL     1       3.278  -2.654   1.631  1.00  0.00           C  
HETATM   27  O6  UNL     1       3.996  -3.055   2.556  1.00  0.00           O  
HETATM   28  C22 UNL     1       3.731  -1.521   0.770  1.00  0.00           C  
HETATM   29  C23 UNL     1       3.427  -0.186   1.404  1.00  0.00           C  
HETATM   30  C24 UNL     1       3.873   0.885   0.422  1.00  0.00           C  
HETATM   31  C25 UNL     1       3.623   2.263   0.942  1.00  0.00           C  
HETATM   32  C26 UNL     1       4.048   3.291  -0.094  1.00  0.00           C  
HETATM   33  C27 UNL     1       3.842   4.692   0.393  1.00  0.00           C  
HETATM   34  C28 UNL     1       4.244   5.698  -0.640  1.00  0.00           C  
HETATM   35  C29 UNL     1       3.450   5.608  -1.916  1.00  0.00           C  
HETATM   36  C30 UNL     1       3.901   6.662  -2.938  1.00  0.00           C  
HETATM   37  C31 UNL     1       3.744   8.001  -2.416  1.00  0.00           C  
HETATM   38  C32 UNL     1       2.996   8.917  -2.941  1.00  0.00           C  
HETATM   39  C33 UNL     1       2.201   8.706  -4.151  1.00  0.00           C  
HETATM   40  C34 UNL     1       0.704   8.910  -3.870  1.00  0.00           C  
HETATM   41  C35 UNL     1      -0.046   8.696  -5.163  1.00  0.00           C  
HETATM   42  C36 UNL     1      -1.540   8.881  -4.968  1.00  0.00           C  
HETATM   43  C37 UNL     1      -2.220   8.651  -6.298  1.00  0.00           C  
HETATM   44  C38 UNL     1      -1.726   9.639  -7.352  1.00  0.00           C  
HETATM   45  C39 UNL     1      -0.453  -5.777   2.188  1.00  0.00           C  
HETATM   46  O7  UNL     1      -0.726  -5.523   3.539  1.00  0.00           O  
HETATM   47  P1  UNL     1      -1.322  -6.916   4.296  1.00  0.00           P  
HETATM   48  O8  UNL     1      -2.079  -7.808   3.360  1.00  0.00           O  
HETATM   49  O9  UNL     1       0.017  -7.718   4.976  1.00  0.00           O  
HETATM   50  O10 UNL     1      -2.311  -6.427   5.590  1.00  0.00           O  
HETATM   51  C40 UNL     1      -2.925  -7.533   6.169  1.00  0.00           C  
HETATM   52  C41 UNL     1      -3.797  -7.100   7.297  1.00  0.00           C  
HETATM   53  O11 UNL     1      -4.424  -8.232   7.874  1.00  0.00           O  
HETATM   54  C42 UNL     1      -2.981  -6.380   8.360  1.00  0.00           C  
HETATM   55  O12 UNL     1      -1.991  -7.214   8.899  1.00  0.00           O  
HETATM   56  P2  UNL     1      -1.134  -6.353  10.080  1.00  0.00           P  
HETATM   57  O13 UNL     1      -1.958  -6.201  11.340  1.00  0.00           O  
HETATM   58  O14 UNL     1       0.260  -7.233  10.447  1.00  0.00           O  
HETATM   59  O15 UNL     1      -0.758  -4.815   9.526  1.00  0.00           O  
HETATM   60  H1  UNL     1      -6.648  -4.793   0.674  1.00  0.00           H  
HETATM   61  H2  UNL     1      -7.026  -4.335  -1.037  1.00  0.00           H  
HETATM   62  H3  UNL     1      -5.315  -4.588  -0.581  1.00  0.00           H  
HETATM   63  H4  UNL     1      -6.284  -2.212  -0.945  1.00  0.00           H  
HETATM   64  H5  UNL     1      -7.076  -2.424   0.675  1.00  0.00           H  
HETATM   65  H6  UNL     1      -4.075  -2.556   0.076  1.00  0.00           H  
HETATM   66  H7  UNL     1      -4.861  -2.859   1.714  1.00  0.00           H  
HETATM   67  H8  UNL     1      -5.799  -0.576   1.645  1.00  0.00           H  
HETATM   68  H9  UNL     1      -5.159  -0.272   0.026  1.00  0.00           H  
HETATM   69  H10 UNL     1      -3.912   0.736   1.912  1.00  0.00           H  
HETATM   70  H11 UNL     1      -3.662  -0.863   2.614  1.00  0.00           H  
HETATM   71  H12 UNL     1      -2.361  -1.716   0.772  1.00  0.00           H  
HETATM   72  H13 UNL     1      -0.852  -0.278  -0.243  1.00  0.00           H  
HETATM   73  H14 UNL     1      -2.557   1.961   1.190  1.00  0.00           H  
HETATM   74  H15 UNL     1      -0.875   2.037   0.747  1.00  0.00           H  
HETATM   75  H16 UNL     1      -2.554   3.356  -0.566  1.00  0.00           H  
HETATM   76  H17 UNL     1      -3.993   1.856  -0.993  1.00  0.00           H  
HETATM   77  H18 UNL     1      -1.228   3.520  -2.437  1.00  0.00           H  
HETATM   78  H19 UNL     1       0.633   2.502  -0.665  1.00  0.00           H  
HETATM   79  H20 UNL     1       0.186   0.892  -1.953  1.00  0.00           H  
HETATM   80  H21 UNL     1       0.505   2.162  -3.119  1.00  0.00           H  
HETATM   81  H22 UNL     1      -2.060   0.427  -3.001  1.00  0.00           H  
HETATM   82  H23 UNL     1      -1.778   1.751  -4.157  1.00  0.00           H  
HETATM   83  H24 UNL     1      -0.037   0.604  -5.353  1.00  0.00           H  
HETATM   84  H25 UNL     1      -1.493  -0.361  -5.189  1.00  0.00           H  
HETATM   85  H26 UNL     1       1.198  -0.856  -3.764  1.00  0.00           H  
HETATM   86  H27 UNL     1       0.433  -1.670  -5.112  1.00  0.00           H  
HETATM   87  H28 UNL     1      -1.220  -2.675  -3.948  1.00  0.00           H  
HETATM   88  H29 UNL     1      -0.868  -1.785  -2.375  1.00  0.00           H  
HETATM   89  H30 UNL     1       1.086  -3.420  -4.146  1.00  0.00           H  
HETATM   90  H31 UNL     1       1.522  -2.612  -2.648  1.00  0.00           H  
HETATM   91  H32 UNL     1      -0.499  -4.892  -2.726  1.00  0.00           H  
HETATM   92  H33 UNL     1       1.284  -5.045  -2.317  1.00  0.00           H  
HETATM   93  H34 UNL     1      -0.454  -3.713   1.552  1.00  0.00           H  
HETATM   94  H35 UNL     1       2.085  -5.254   1.958  1.00  0.00           H  
HETATM   95  H36 UNL     1       1.275  -4.104   3.168  1.00  0.00           H  
HETATM   96  H37 UNL     1       4.829  -1.600   0.643  1.00  0.00           H  
HETATM   97  H38 UNL     1       3.295  -1.615  -0.231  1.00  0.00           H  
HETATM   98  H39 UNL     1       2.312  -0.095   1.504  1.00  0.00           H  
HETATM   99  H40 UNL     1       3.919  -0.049   2.371  1.00  0.00           H  
HETATM  100  H41 UNL     1       4.895   0.704   0.071  1.00  0.00           H  
HETATM  101  H42 UNL     1       3.209   0.748  -0.482  1.00  0.00           H  
HETATM  102  H43 UNL     1       4.196   2.424   1.869  1.00  0.00           H  
HETATM  103  H44 UNL     1       2.519   2.347   1.101  1.00  0.00           H  
HETATM  104  H45 UNL     1       3.482   3.156  -1.038  1.00  0.00           H  
HETATM  105  H46 UNL     1       5.120   3.179  -0.346  1.00  0.00           H  
HETATM  106  H47 UNL     1       2.751   4.798   0.650  1.00  0.00           H  
HETATM  107  H48 UNL     1       4.433   4.870   1.337  1.00  0.00           H  
HETATM  108  H49 UNL     1       4.155   6.739  -0.208  1.00  0.00           H  
HETATM  109  H50 UNL     1       5.349   5.595  -0.842  1.00  0.00           H  
HETATM  110  H51 UNL     1       3.666   4.604  -2.387  1.00  0.00           H  
HETATM  111  H52 UNL     1       2.390   5.736  -1.689  1.00  0.00           H  
HETATM  112  H53 UNL     1       5.019   6.489  -3.057  1.00  0.00           H  
HETATM  113  H54 UNL     1       3.482   6.425  -3.910  1.00  0.00           H  
HETATM  114  H55 UNL     1       4.308   8.262  -1.509  1.00  0.00           H  
HETATM  115  H56 UNL     1       2.914   9.940  -2.492  1.00  0.00           H  
HETATM  116  H57 UNL     1       2.410   7.834  -4.752  1.00  0.00           H  
HETATM  117  H58 UNL     1       2.444   9.589  -4.828  1.00  0.00           H  
HETATM  118  H59 UNL     1       0.369   8.219  -3.075  1.00  0.00           H  
HETATM  119  H60 UNL     1       0.596   9.965  -3.551  1.00  0.00           H  
HETATM  120  H61 UNL     1       0.128   7.664  -5.493  1.00  0.00           H  
HETATM  121  H62 UNL     1       0.305   9.401  -5.941  1.00  0.00           H  
HETATM  122  H63 UNL     1      -1.788   9.869  -4.567  1.00  0.00           H  
HETATM  123  H64 UNL     1      -1.895   8.081  -4.285  1.00  0.00           H  
HETATM  124  H65 UNL     1      -3.320   8.684  -6.250  1.00  0.00           H  
HETATM  125  H66 UNL     1      -1.954   7.637  -6.710  1.00  0.00           H  
HETATM  126  H67 UNL     1      -1.582  10.620  -6.901  1.00  0.00           H  
HETATM  127  H68 UNL     1      -0.740   9.321  -7.775  1.00  0.00           H  
HETATM  128  H69 UNL     1      -2.441   9.688  -8.178  1.00  0.00           H  
HETATM  129  H70 UNL     1       0.159  -6.717   2.115  1.00  0.00           H  
HETATM  130  H71 UNL     1      -1.444  -6.086   1.740  1.00  0.00           H  
HETATM  131  H72 UNL     1       0.205  -7.375   5.877  1.00  0.00           H  
HETATM  132  H73 UNL     1      -2.131  -8.196   6.622  1.00  0.00           H  
HETATM  133  H74 UNL     1      -3.444  -8.149   5.423  1.00  0.00           H  
HETATM  134  H75 UNL     1      -4.615  -6.448   6.974  1.00  0.00           H  
HETATM  135  H76 UNL     1      -5.135  -7.903   8.466  1.00  0.00           H  
HETATM  136  H77 UNL     1      -2.490  -5.509   7.889  1.00  0.00           H  
HETATM  137  H78 UNL     1      -3.615  -6.030   9.194  1.00  0.00           H  
HETATM  138  H79 UNL     1       0.646  -7.635   9.624  1.00  0.00           H  
HETATM  139  H80 UNL     1      -0.600  -4.775   8.566  1.00  0.00           H  
CONECT    1    2   60   61   62
CONECT    2    3   63   64
CONECT    3    4   65   66
CONECT    4    5   67   68
CONECT    5    6   69   70
CONECT    6    7    7   71
CONECT    7    8   72
CONECT    8    9   73   74
CONECT    9   10   11   75
CONECT   10   76
CONECT   11   12   13   77
CONECT   12   78
CONECT   13   14   79   80
CONECT   14   15   81   82
CONECT   15   16   83   84
CONECT   16   17   85   86
CONECT   17   18   87   88
CONECT   18   19   89   90
CONECT   19   20   91   92
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   45   93
CONECT   24   25   94   95
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   96   97
CONECT   29   30   98   99
CONECT   30   31  100  101
CONECT   31   32  102  103
CONECT   32   33  104  105
CONECT   33   34  106  107
CONECT   34   35  108  109
CONECT   35   36  110  111
CONECT   36   37  112  113
CONECT   37   38   38  114
CONECT   38   39  115
CONECT   39   40  116  117
CONECT   40   41  118  119
CONECT   41   42  120  121
CONECT   42   43  122  123
CONECT   43   44  124  125
CONECT   44  126  127  128
CONECT   45   46  129  130
CONECT   46   47
CONECT   47   48   48   49   50
CONECT   49  131
CONECT   50   51
CONECT   51   52  132  133
CONECT   52   53   54  134
CONECT   53  135
CONECT   54   55  136  137
CONECT   55   56
CONECT   56   57   57   58   59
CONECT   58  138
CONECT   59  139
END

HMDB0272658
     RDKit          3D
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))
139138  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2S)-3-({[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate	Generator

Chemical Formula

C₄₂H₈₀O₁₅P₂

Average Molecular Weight

887.035

Monoisotopic Molecular Weight

886.497245872

IUPAC Name

[(2S)-3-({[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H80O15P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-23-27-31-41(46)53-35-38(36-56-59(51,52)55-34-37(43)33-54-58(48,49)50)57-42(47)32-28-24-20-22-26-30-40(45)39(44)29-25-21-10-8-6-4-2/h12-13,21,25,37-40,43-45H,3-11,14-20,22-24,26-36H2,1-2H3,(H,51,52)(H2,48,49,50)/b13-12-,25-21-/t37-,38+,39-,40-/m0/s1

InChI Key

LEKKVGFOGZWYCI-ITOGZDHKSA-N

Chemical Taxonomy

Classification

Not classified

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.02	ALOGPS
logP	9.41	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	235.81 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	229.85 m³·mol⁻¹	ChemAxon
Polarizability	99.67 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
AllCCS	[M+H]+	301.307	32859911
AllCCS	[M+H-H2O]+	301.546	32859911
AllCCS	[M+Na]+	300.97	32859911
AllCCS	[M+NH4]+	301.051	32859911
AllCCS	[M-H]-	299.482	32859911
AllCCS	[M+Na-2H]-	306.095	32859911
AllCCS	[M+HCOO]-	313.347	32859911
DeepCCS	[M+H]+	289.825	30932474
DeepCCS	[M-H]-	287.429	30932474
DeepCCS	[M-2H]-	320.641	30932474
DeepCCS	[M+Na]+	295.737	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC[C@H](O)[C@@H](O)C\C=C/CCCCC	5457.6	Standard polar	33892256
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC[C@H](O)[C@@H](O)C\C=C/CCCCC	4800.6	Standard non polar	33892256
PGP(18:1(11Z)/18:1(12Z)-2OH(9,10))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC[C@H](O)[C@@H](O)C\C=C/CCCCC	6215.7	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 10V, Negative-QTOF	splash10-000i-0010000090-82f63436625f5c297c7e	2021-10-18	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 20V, Negative-QTOF	splash10-0f79-3190143040-28f6e920684095d193b8	2021-10-18	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 40V, Negative-QTOF	splash10-0pba-3091260100-5d734fc9cc12ec75524d	2021-10-18	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 10V, Positive-QTOF	splash10-00kr-1100013490-4afa69019a85c9de053a	2021-10-18	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 20V, Positive-QTOF	splash10-0079-1400009810-43e7e664bc4dda276297	2021-10-18	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) 40V, Positive-QTOF	splash10-0udi-3960232100-d55b0394b02aa0c55e82	2021-10-18	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

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

Hajeyah AA, Griffiths WJ, Wang Y, Finch AJ, O'Donnell VB: The Biosynthesis of Enzymatically Oxidized Lipids. Front Endocrinol (Lausanne). 2020 Nov 19;11:591819. doi: 10.3389/fendo.2020.591819. eCollection 2020. [PubMed:33329396 ]

Showing metabocard for PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)) (HMDB0272658)

MOL for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

3D MOL for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

3D SDF for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

3D-SDF for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

PDB for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

3D PDB for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

SMILES for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

INCHI for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

Structure for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

3D Structure for HMDB0272658 (PGP(18:1(11Z)/18:1(12Z)-2OH(9,10)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra