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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 18:46:20 UTC

Update Date

2022-11-30 19:58:16 UTC

HMDB ID

HMDB0270939

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PG(a-21:0/20:3(6,8,11)-OH(5))

Description

PG(a-21:0/20:3(6,8,11)-OH(5)) is an oxidized phosphatidylglycerol (PG). Oxidized phosphatidylglycerols 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 phosphatidylglycerols 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, phosphatidylglycerols 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. PG(a-21:0/20:3(6,8,11)-OH(5)), in particular, consists of one chain of one 18-methyleicosanoyl at the C-1 position and one chain of 5-hydroxyeicosatetrienoyl 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 PGs can be synthesized via three different routes. In one route, the oxidized PG is synthetized de novo following the same mechanisms as for PGs 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 PG backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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

PG(a-21:0/20:3(6,8,11)-OH(5))
  Mrv1652309122120462D          

 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
    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
  -12.3673    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0815    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7956    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5097    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2239    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9380    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6521    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.3662    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.3662   -0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.0803    0.3576    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
   -6.3660   -1.5394    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   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
  -12.0789   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7930   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5071   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2212   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9354   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6495   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3636   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0777   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 15  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 12  1  0  0  0  0
  8 11  1  6  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 13  1  1  0  0  0  0
 14 13  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 15 14  1  0  0  0  0
 17 40  1  0  0  0  0
 18 19  2  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  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  1  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
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 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
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  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

HMDB0270939
     RDKit          3D
PG(a-21:0/20:3(6,8,11)-OH(5))
146145  0  0  0  0  0  0  0  0999 V2000
   17.9548    1.7726    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2619    0.4453    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2347    0.7294    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4781   -0.5004    2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4347   -0.2952    3.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1510    0.3471    2.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9284    1.6326    2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0368    1.5382    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8979    0.6100    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9519    1.0353   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8916    0.0865   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5128    0.4705   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2076    1.6651   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9153    2.0511    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725    2.4958    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923    2.1525    0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    3.2782    0.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    1.0072    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    0.9640    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068    0.7292   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659   -0.4576   -0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   -0.3488   -2.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509   -1.7237   -0.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673   -2.7437   -1.2952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5284   -3.1842   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4663   -2.1557   -0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -1.4014   -2.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -1.6104   -3.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213   -0.3418   -1.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302   -0.2145   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5192    0.8463   -0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9781    0.9642    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5591   -0.2583    1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8915   -0.6783    0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2665   -1.9438    1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4649   -2.7260    1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8286   -2.3450    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6771   -1.3631    0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2910    0.0505    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3717    0.9842    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5478    0.9502    1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6918    1.8575    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2442    1.4593   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3531    2.2694   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6141    2.3848   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5557    2.9984    1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4127    1.1065   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7686    0.6562   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979   -3.9221   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -3.6104   -1.7918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -4.5127   -2.1311 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.1168   -5.9174   -1.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931   -4.5852   -3.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5903   -3.7881   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1121   -2.7394   -2.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0648   -1.6540   -2.1694 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5060   -1.2816   -0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155   -0.4308   -2.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    0.2843   -3.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8750    1.9062    0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2038    1.8387   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1790    2.5507    0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7291    0.1131   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9805   -0.2992    0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7033    1.6498    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9211    0.9170    2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0922   -1.0262    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1941   -1.2747    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9182    0.2658    3.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1992   -1.3026    3.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4231   -0.4521    2.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6917    0.4553    3.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6061    2.4498    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8819    2.0223    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9147    1.0728    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8880    2.4929    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8316   -0.3875    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0398    2.0481   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0304   -0.8999   -0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0303   -0.1504   -2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -0.1827   -0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    2.2989   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3365    2.7453    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    3.6735    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    1.8749   -0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547    3.4367    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890    0.0772    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    1.2960    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9730    0.2445    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462    2.0172    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0644    1.5620   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    1.2015   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -2.3675   -2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7406   -0.5763   -2.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5904    0.2092    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7084   -1.1667   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682    1.8182   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3222    0.5965   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714    1.2562    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    1.8142    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8643   -1.1158    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8535   -0.0673    2.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7380   -0.7298   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5786    0.1391    1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2054   -1.8159    2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3294   -2.6436    1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4171   -3.0741    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2628   -3.7990    1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4586   -3.3508    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9407   -2.2365    2.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7185   -1.5034    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8422   -1.6823   -0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4791    0.1468    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9555    0.4056    1.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6223    0.6560   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9354    2.0199    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9407   -0.0428    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1771    1.3932    2.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3003    2.8940    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3950    1.8714    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4320    0.3521   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3745    1.5906   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9548    3.3208   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5325    1.9363   -2.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.2818    3.0699   -0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4844    3.6492    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7142    3.7133    1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6575    2.2233    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.3765    1.3585    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9531    0.3247    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1931    1.5426   -2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.6315   -0.0690   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9568    0.1529   -2.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -4.3489   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2748   -4.7412   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454   -4.9130   -3.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184   -3.0975   -3.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9506   -2.3371   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2221   -2.0848   -2.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6233   -1.9964   -0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1742   -0.5278   -3.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474    0.3324   -2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.1487   -3.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
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 23 24  1  0
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 26 27  1  0
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 29 30  1  0
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 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
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 58 59  1  0
  1 60  1  0
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 55140  1  0
 55141  1  0
 56142  1  6
 57143  1  0
 58144  1  0
 58145  1  0
 59146  1  0
M  END

PG(a-21:0/20:3(6,8,11)-OH(5))
  Mrv1652309122120462D          

 61 60  0  0  1  0            999 V2000
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    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
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
   -6.3660   -1.5394    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   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
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  1 18  1  0  0  0  0
  2 15  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 12  1  0  0  0  0
  8 11  1  6  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 13  1  1  0  0  0  0
 14 13  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 15 14  1  0  0  0  0
 17 40  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
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 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  1  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
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 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
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  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>
HMDB0270939

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C47H87O11P/c1-4-6-7-8-9-10-11-14-18-21-24-27-30-34-43(49)35-32-37-47(52)58-45(41-57-59(53,54)56-39-44(50)38-48)40-55-46(51)36-31-28-25-22-19-16-13-12-15-17-20-23-26-29-33-42(3)5-2/h14,18,24,27,30,34,42-45,48-50H,4-13,15-17,19-23,25-26,28-29,31-33,35-41H2,1-3H3,(H,53,54)/b18-14+,27-24+,34-30+/t42?,43?,44-,45+/m0/s1

> <INCHI_KEY>
GJFDYPPLIQUMKG-FPZQPSPOSA-N

> <FORMULA>
C47H87O11P

> <MOLECULAR_WEIGHT>
859.176

> <EXACT_MASS>
858.598600619

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
146

> <JCHEM_AVERAGE_POLARIZABILITY>
104.74892859206206

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
8.56

> <JCHEM_LOGP>
12.464043898666667

> <ALOGPS_LOGS>
-6.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.641245576372423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8909327841325134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5456712019080712

> <JCHEM_POLAR_SURFACE_AREA>
169.05

> <JCHEM_REFRACTIVITY>
241.53080000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
45

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.87e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy((2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0270939
     RDKit          3D
PG(a-21:0/20:3(6,8,11)-OH(5))
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M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG(a-21:0/20:3(6,8,11)-OH(5))                     
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
HETATM   10  O   UNK     0       6.138   2.284   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       4.315   3.545   0.000  0.00  0.00           H+0
HETATM   12  O   UNK     0       2.775   3.545   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.086   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.419   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.752   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -27.085   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -28.418   0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -29.751   1.436   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -31.084   0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -32.417   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -32.417  -0.103   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -33.750   0.668   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -11.883  -2.873   0.000  0.00  0.00           O+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  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -22.547  -1.433   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -23.880  -0.662   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -25.213  -1.433   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -26.546  -0.662   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -27.879  -1.433   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -29.212  -0.662   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -30.545  -1.433   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -31.878  -0.662   0.000  0.00  0.00           C+0
CONECT    1   18   13                                                       
CONECT    2   15    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12   11    9                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    1   14                                                       
CONECT   14   13   16   17   15                                             
CONECT   15    2   14                                                       
CONECT   16   14                                                            
CONECT   17   14   40                                                       
CONECT   18    1   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                                                       
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   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   17   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   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    HMDB0270939
HETATM    1  C1  UNL     1      17.955   1.773   0.248  1.00  0.00           C  
HETATM    2  C2  UNL     1      17.262   0.445   0.570  1.00  0.00           C  
HETATM    3  C3  UNL     1      16.235   0.729   1.654  1.00  0.00           C  
HETATM    4  C4  UNL     1      15.478  -0.500   2.066  1.00  0.00           C  
HETATM    5  C5  UNL     1      14.435  -0.295   3.078  1.00  0.00           C  
HETATM    6  C6  UNL     1      13.151   0.347   2.880  1.00  0.00           C  
HETATM    7  C7  UNL     1      12.928   1.633   2.221  1.00  0.00           C  
HETATM    8  C8  UNL     1      13.037   1.538   0.715  1.00  0.00           C  
HETATM    9  C9  UNL     1      11.898   0.610   0.290  1.00  0.00           C  
HETATM   10  C10 UNL     1      10.952   1.035  -0.569  1.00  0.00           C  
HETATM   11  C11 UNL     1       9.892   0.086  -0.932  1.00  0.00           C  
HETATM   12  C12 UNL     1       8.513   0.471  -0.674  1.00  0.00           C  
HETATM   13  C13 UNL     1       8.208   1.665  -0.158  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.915   2.051   0.095  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.773   2.496   0.364  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.392   2.153   0.327  1.00  0.00           C  
HETATM   17  O1  UNL     1       3.560   3.278   0.557  1.00  0.00           O  
HETATM   18  C17 UNL     1       3.884   1.007   1.205  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.413   0.964   0.994  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.707   0.729  -0.214  1.00  0.00           C  
HETATM   21  C20 UNL     1       1.466  -0.458  -0.978  1.00  0.00           C  
HETATM   22  O2  UNL     1       1.417  -0.349  -2.259  1.00  0.00           O  
HETATM   23  O3  UNL     1       1.251  -1.724  -0.406  1.00  0.00           O  
HETATM   24  C21 UNL     1       0.867  -2.744  -1.295  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.528  -3.184  -0.893  1.00  0.00           C  
HETATM   26  O4  UNL     1      -1.466  -2.156  -0.959  1.00  0.00           O  
HETATM   27  C23 UNL     1      -1.865  -1.401  -2.012  1.00  0.00           C  
HETATM   28  O5  UNL     1      -1.328  -1.610  -3.125  1.00  0.00           O  
HETATM   29  C24 UNL     1      -2.921  -0.342  -1.880  1.00  0.00           C  
HETATM   30  C25 UNL     1      -3.430  -0.215  -0.488  1.00  0.00           C  
HETATM   31  C26 UNL     1      -4.519   0.846  -0.426  1.00  0.00           C  
HETATM   32  C27 UNL     1      -4.978   0.964   1.011  1.00  0.00           C  
HETATM   33  C28 UNL     1      -5.559  -0.258   1.606  1.00  0.00           C  
HETATM   34  C29 UNL     1      -6.891  -0.678   0.906  1.00  0.00           C  
HETATM   35  C30 UNL     1      -7.267  -1.944   1.567  1.00  0.00           C  
HETATM   36  C31 UNL     1      -8.465  -2.726   1.283  1.00  0.00           C  
HETATM   37  C32 UNL     1      -9.829  -2.345   1.499  1.00  0.00           C  
HETATM   38  C33 UNL     1     -10.677  -1.363   0.866  1.00  0.00           C  
HETATM   39  C34 UNL     1     -10.291   0.050   0.830  1.00  0.00           C  
HETATM   40  C35 UNL     1     -11.372   0.984   0.284  1.00  0.00           C  
HETATM   41  C36 UNL     1     -12.548   0.950   1.194  1.00  0.00           C  
HETATM   42  C37 UNL     1     -13.692   1.857   0.781  1.00  0.00           C  
HETATM   43  C38 UNL     1     -14.244   1.459  -0.549  1.00  0.00           C  
HETATM   44  C39 UNL     1     -15.353   2.269  -1.081  1.00  0.00           C  
HETATM   45  C40 UNL     1     -16.614   2.385  -0.325  1.00  0.00           C  
HETATM   46  C41 UNL     1     -16.556   2.998   1.035  1.00  0.00           C  
HETATM   47  C42 UNL     1     -17.413   1.107  -0.230  1.00  0.00           C  
HETATM   48  C43 UNL     1     -17.769   0.656  -1.633  1.00  0.00           C  
HETATM   49  C44 UNL     1       1.798  -3.922  -1.334  1.00  0.00           C  
HETATM   50  O6  UNL     1       2.950  -3.610  -1.792  1.00  0.00           O  
HETATM   51  P1  UNL     1       4.278  -4.513  -2.131  1.00  0.00           P  
HETATM   52  O7  UNL     1       4.117  -5.917  -1.579  1.00  0.00           O  
HETATM   53  O8  UNL     1       4.693  -4.585  -3.743  1.00  0.00           O  
HETATM   54  O9  UNL     1       5.590  -3.788  -1.258  1.00  0.00           O  
HETATM   55  C45 UNL     1       6.112  -2.739  -2.084  1.00  0.00           C  
HETATM   56  C46 UNL     1       5.065  -1.654  -2.169  1.00  0.00           C  
HETATM   57  O10 UNL     1       4.506  -1.282  -0.995  1.00  0.00           O  
HETATM   58  C47 UNL     1       5.516  -0.431  -2.895  1.00  0.00           C  
HETATM   59  O11 UNL     1       4.330   0.284  -3.281  1.00  0.00           O  
HETATM   60  H1  UNL     1      18.875   1.906   0.842  1.00  0.00           H  
HETATM   61  H2  UNL     1      18.204   1.839  -0.804  1.00  0.00           H  
HETATM   62  H3  UNL     1      17.179   2.551   0.487  1.00  0.00           H  
HETATM   63  H4  UNL     1      16.729   0.113  -0.345  1.00  0.00           H  
HETATM   64  H5  UNL     1      17.980  -0.299   0.940  1.00  0.00           H  
HETATM   65  H6  UNL     1      15.703   1.650   1.561  1.00  0.00           H  
HETATM   66  H7  UNL     1      16.921   0.917   2.585  1.00  0.00           H  
HETATM   67  H8  UNL     1      15.092  -1.026   1.151  1.00  0.00           H  
HETATM   68  H9  UNL     1      16.194  -1.275   2.498  1.00  0.00           H  
HETATM   69  H10 UNL     1      14.918   0.266   3.988  1.00  0.00           H  
HETATM   70  H11 UNL     1      14.199  -1.303   3.599  1.00  0.00           H  
HETATM   71  H12 UNL     1      12.423  -0.452   2.479  1.00  0.00           H  
HETATM   72  H13 UNL     1      12.692   0.455   3.953  1.00  0.00           H  
HETATM   73  H14 UNL     1      13.606   2.450   2.566  1.00  0.00           H  
HETATM   74  H15 UNL     1      11.882   2.022   2.410  1.00  0.00           H  
HETATM   75  H16 UNL     1      13.915   1.073   0.320  1.00  0.00           H  
HETATM   76  H17 UNL     1      12.888   2.493   0.200  1.00  0.00           H  
HETATM   77  H18 UNL     1      11.832  -0.388   0.633  1.00  0.00           H  
HETATM   78  H19 UNL     1      11.040   2.048  -0.933  1.00  0.00           H  
HETATM   79  H20 UNL     1      10.030  -0.900  -0.410  1.00  0.00           H  
HETATM   80  H21 UNL     1      10.030  -0.150  -2.038  1.00  0.00           H  
HETATM   81  H22 UNL     1       7.674  -0.183  -0.848  1.00  0.00           H  
HETATM   82  H23 UNL     1       9.097   2.299  -0.000  1.00  0.00           H  
HETATM   83  H24 UNL     1       7.337   2.745   1.298  1.00  0.00           H  
HETATM   84  H25 UNL     1       5.950   3.674   0.547  1.00  0.00           H  
HETATM   85  H26 UNL     1       4.130   1.875  -0.742  1.00  0.00           H  
HETATM   86  H27 UNL     1       3.655   3.437   1.548  1.00  0.00           H  
HETATM   87  H28 UNL     1       4.389   0.077   1.048  1.00  0.00           H  
HETATM   88  H29 UNL     1       4.041   1.296   2.287  1.00  0.00           H  
HETATM   89  H30 UNL     1       1.973   0.244   1.803  1.00  0.00           H  
HETATM   90  H31 UNL     1       2.046   2.017   1.389  1.00  0.00           H  
HETATM   91  H32 UNL     1       2.064   1.562  -1.016  1.00  0.00           H  
HETATM   92  H33 UNL     1       0.635   1.201  -0.075  1.00  0.00           H  
HETATM   93  H34 UNL     1       0.768  -2.367  -2.358  1.00  0.00           H  
HETATM   94  H35 UNL     1      -0.915  -4.008  -1.546  1.00  0.00           H  
HETATM   95  H36 UNL     1      -0.526  -3.598   0.139  1.00  0.00           H  
HETATM   96  H37 UNL     1      -2.480   0.634  -2.215  1.00  0.00           H  
HETATM   97  H38 UNL     1      -3.741  -0.576  -2.561  1.00  0.00           H  
HETATM   98  H39 UNL     1      -2.590   0.209   0.147  1.00  0.00           H  
HETATM   99  H40 UNL     1      -3.708  -1.167  -0.022  1.00  0.00           H  
HETATM  100  H41 UNL     1      -4.068   1.818  -0.699  1.00  0.00           H  
HETATM  101  H42 UNL     1      -5.322   0.596  -1.135  1.00  0.00           H  
HETATM  102  H43 UNL     1      -4.071   1.256   1.608  1.00  0.00           H  
HETATM  103  H44 UNL     1      -5.698   1.814   1.089  1.00  0.00           H  
HETATM  104  H45 UNL     1      -4.864  -1.116   1.637  1.00  0.00           H  
HETATM  105  H46 UNL     1      -5.854  -0.067   2.658  1.00  0.00           H  
HETATM  106  H47 UNL     1      -6.738  -0.730  -0.168  1.00  0.00           H  
HETATM  107  H48 UNL     1      -7.579   0.139   1.257  1.00  0.00           H  
HETATM  108  H49 UNL     1      -7.205  -1.816   2.722  1.00  0.00           H  
HETATM  109  H50 UNL     1      -6.329  -2.644   1.451  1.00  0.00           H  
HETATM  110  H51 UNL     1      -8.417  -3.074   0.154  1.00  0.00           H  
HETATM  111  H52 UNL     1      -8.263  -3.799   1.735  1.00  0.00           H  
HETATM  112  H53 UNL     1     -10.459  -3.351   1.439  1.00  0.00           H  
HETATM  113  H54 UNL     1      -9.941  -2.237   2.684  1.00  0.00           H  
HETATM  114  H55 UNL     1     -11.718  -1.503   1.338  1.00  0.00           H  
HETATM  115  H56 UNL     1     -10.842  -1.682  -0.221  1.00  0.00           H  
HETATM  116  H57 UNL     1      -9.479   0.147   0.036  1.00  0.00           H  
HETATM  117  H58 UNL     1      -9.956   0.406   1.814  1.00  0.00           H  
HETATM  118  H59 UNL     1     -11.622   0.656  -0.730  1.00  0.00           H  
HETATM  119  H60 UNL     1     -10.935   2.020   0.328  1.00  0.00           H  
HETATM  120  H61 UNL     1     -12.941  -0.043   1.446  1.00  0.00           H  
HETATM  121  H62 UNL     1     -12.177   1.393   2.172  1.00  0.00           H  
HETATM  122  H63 UNL     1     -13.300   2.894   0.690  1.00  0.00           H  
HETATM  123  H64 UNL     1     -14.395   1.871   1.623  1.00  0.00           H  
HETATM  124  H65 UNL     1     -14.432   0.352  -0.597  1.00  0.00           H  
HETATM  125  H66 UNL     1     -13.375   1.591  -1.269  1.00  0.00           H  
HETATM  126  H67 UNL     1     -14.955   3.321  -1.218  1.00  0.00           H  
HETATM  127  H68 UNL     1     -15.532   1.936  -2.146  1.00  0.00           H  
HETATM  128  H69 UNL     1     -17.282   3.070  -0.952  1.00  0.00           H  
HETATM  129  H70 UNL     1     -17.484   3.649   1.174  1.00  0.00           H  
HETATM  130  H71 UNL     1     -15.714   3.713   1.166  1.00  0.00           H  
HETATM  131  H72 UNL     1     -16.658   2.223   1.798  1.00  0.00           H  
HETATM  132  H73 UNL     1     -18.377   1.359   0.264  1.00  0.00           H  
HETATM  133  H74 UNL     1     -16.953   0.325   0.378  1.00  0.00           H  
HETATM  134  H75 UNL     1     -18.193   1.543  -2.162  1.00  0.00           H  
HETATM  135  H76 UNL     1     -18.632  -0.069  -1.565  1.00  0.00           H  
HETATM  136  H77 UNL     1     -16.957   0.153  -2.153  1.00  0.00           H  
HETATM  137  H78 UNL     1       1.809  -4.349  -0.263  1.00  0.00           H  
HETATM  138  H79 UNL     1       1.275  -4.741  -1.930  1.00  0.00           H  
HETATM  139  H80 UNL     1       5.645  -4.913  -3.807  1.00  0.00           H  
HETATM  140  H81 UNL     1       6.418  -3.098  -3.048  1.00  0.00           H  
HETATM  141  H82 UNL     1       6.951  -2.337  -1.503  1.00  0.00           H  
HETATM  142  H83 UNL     1       4.222  -2.085  -2.812  1.00  0.00           H  
HETATM  143  H84 UNL     1       4.623  -1.996  -0.265  1.00  0.00           H  
HETATM  144  H85 UNL     1       6.174  -0.528  -3.726  1.00  0.00           H  
HETATM  145  H86 UNL     1       5.947   0.332  -2.152  1.00  0.00           H  
HETATM  146  H87 UNL     1       4.553   1.149  -3.679  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   71   72
CONECT    7    8   73   74
CONECT    8    9   75   76
CONECT    9   10   10   77
CONECT   10   11   78
CONECT   11   12   79   80
CONECT   12   13   13   81
CONECT   13   14   82
CONECT   14   15   15   83
CONECT   15   16   84
CONECT   16   17   18   85
CONECT   17   86
CONECT   18   19   87   88
CONECT   19   20   89   90
CONECT   20   21   91   92
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   49   93
CONECT   25   26   94   95
CONECT   26   27
CONECT   27   28   28   29
CONECT   29   30   96   97
CONECT   30   31   98   99
CONECT   31   32  100  101
CONECT   32   33  102  103
CONECT   33   34  104  105
CONECT   34   35  106  107
CONECT   35   36  108  109
CONECT   36   37  110  111
CONECT   37   38  112  113
CONECT   38   39  114  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   45  126  127
CONECT   45   46   47  128
CONECT   46  129  130  131
CONECT   47   48  132  133
CONECT   48  134  135  136
CONECT   49   50  137  138
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53  139
CONECT   54   55
CONECT   55   56  140  141
CONECT   56   57   58  142
CONECT   57  143
CONECT   58   59  144  145
CONECT   59  146
END

HMDB0270939
     RDKit          3D
PG(a-21:0/20:3(6,8,11)-OH(5))
146145  0  0  0  0  0  0  0  0999 V2000
   17.9548    1.7726    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2619    0.4453    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2347    0.7294    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4781   -0.5004    2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4347   -0.2952    3.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1510    0.3471    2.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9284    1.6326    2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0368    1.5382    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8979    0.6100    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9519    1.0353   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4649   -2.7260    1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2S)-2,3-Dihydroxypropoxy][(2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy]phosphinate	Generator

Chemical Formula

C₄₇H₈₇O₁₁P

Average Molecular Weight

859.176

Monoisotopic Molecular Weight

858.598600619

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC

InChI Identifier

InChI=1S/C47H87O11P/c1-4-6-7-8-9-10-11-14-18-21-24-27-30-34-43(49)35-32-37-47(52)58-45(41-57-59(53,54)56-39-44(50)38-48)40-55-46(51)36-31-28-25-22-19-16-13-12-15-17-20-23-26-29-33-42(3)5-2/h14,18,24,27,30,34,42-45,48-50H,4-13,15-17,19-23,25-26,28-29,31-33,35-41H2,1-3H3,(H,53,54)/b18-14+,27-24+,34-30+/t42?,43?,44-,45+/m0/s1

InChI Key

GJFDYPPLIQUMKG-FPZQPSPOSA-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	8.56	ALOGPS
logP	12.46	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	45	ChemAxon
Refractivity	241.53 m³·mol⁻¹	ChemAxon
Polarizability	104.75 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]+	301.625	32859911
AllCCS	[M+H-H2O]+	301.731	32859911
AllCCS	[M+Na]+	301.454	32859911
AllCCS	[M+NH4]+	301.497	32859911
AllCCS	[M-H]-	297.095	32859911
AllCCS	[M+Na-2H]-	303.837	32859911
AllCCS	[M+HCOO]-	311.225	32859911
DeepCCS	[M+H]+	285.595	30932474
DeepCCS	[M-H]-	283.2	30932474
DeepCCS	[M-2H]-	316.083	30932474
DeepCCS	[M+Na]+	291.508	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PG(a-21:0/20:3(6,8,11)-OH(5))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC	5547.2	Standard polar	33892256
PG(a-21:0/20:3(6,8,11)-OH(5))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC	5070.0	Standard non polar	33892256
PG(a-21:0/20:3(6,8,11)-OH(5))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC	6065.3	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 - PG(a-21:0/20:3(6,8,11)-OH(5)) 10V, Negative-QTOF	splash10-0a4i-0000000090-1420f231a25ba465923b	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(a-21:0/20:3(6,8,11)-OH(5)) 20V, Negative-QTOF	splash10-0adi-0009130040-961034153491f9697a11	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(a-21:0/20:3(6,8,11)-OH(5)) 40V, Negative-QTOF	splash10-0ak9-0109130040-5bbecebea5c72c84d020	2021-09-28	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 PG(a-21:0/20:3(6,8,11)-OH(5)) (HMDB0270939)

MOL for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

3D MOL for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

3D SDF for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

3D-SDF for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

PDB for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

3D PDB for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

SMILES for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

INCHI for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

Structure for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

3D Structure for HMDB0270939 (PG(a-21:0/20:3(6,8,11)-OH(5)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra