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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 21:01:50 UTC

Update Date

2022-11-30 19:58:47 UTC

HMDB ID

HMDB0272160

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)

Description

PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0) 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(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0), in particular, consists of one chain of one 5(S),15(S)-Dihydroxyeicosatetraenoyl at the C-1 position and one chain of 20-methylheneicosanoyl 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(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)
  Mrv1652309122123022D          

 63 62  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  1  0  0  0  0  0  0  0  0  0
   -7.3686    1.5410    0.0000 O   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
  -10.3359    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0500    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7641    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5891    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3032    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0173    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7315    0.7695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.7315    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4456    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1597    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8738    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5879    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.3020    0.3564    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  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
  -17.7918   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7918    0.0571    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 41  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  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 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  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  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
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
M  END

HMDB0272160
     RDKit          3D
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)
148147  0  0  0  0  0  0  0  0999 V2000
   -2.4648    8.0837   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469    8.2416   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    7.0596    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    5.7827    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0913    5.8936    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8728    4.6374    0.5284 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3336    3.5635    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9462    4.2862   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3157    3.0419   -1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3987    2.6603   -2.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7678    1.4527   -3.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176    0.4171   -2.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4149   -0.8398   -1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -1.2204   -2.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6473   -0.4553   -3.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -1.0164   -4.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -0.3201   -5.2295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9948   -1.2693   -5.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491    0.7269   -4.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    1.3875   -5.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829    2.4619   -5.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    2.0948   -4.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7172    2.4858   -3.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    1.3380   -4.4770 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571    1.0088   -3.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383    0.2625   -2.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7855    0.1429   -1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017   -0.3518   -0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7628   -0.4989    0.7837 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.4245   -0.3589    2.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8494    0.7201    0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4239   -2.0341    0.4973 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -2.9758    1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1036   -4.3858    0.8556 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3682   -4.4534    1.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -5.3138    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -6.6361    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0158   -0.9999   -2.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8274   -1.5061   -2.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -0.7236   -1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -2.9214   -2.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -3.0892   -2.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169   -4.5529   -2.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3432   -5.2513   -1.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -4.6188   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -5.1953    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -4.9148    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585   -5.4606    2.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -5.1102    3.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2024   -3.5948    3.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -3.0534    4.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -1.5826    4.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -0.9986    5.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    0.4630    5.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688    1.3445    4.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.2193    3.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0207    2.0848    2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    1.8059    1.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927    2.6591    0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745    4.1233    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988    2.3167   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    9.1058   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939    7.5476   -2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    7.6434   -1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    9.1015    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4698    8.5181    0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    7.2778    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291    6.9495    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    5.4765   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1631    4.9733    0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1732    6.1174    1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6083    6.7204    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9217    4.8037    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3815    3.7715    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7220    4.9676   -1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5294    2.3818   -0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1451    3.4104   -3.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8414    1.3085   -4.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2777    0.7825   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2486    0.1788   -2.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8341   -1.5793   -1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9835   -2.2361   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8363    0.5240   -3.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128   -2.0272   -3.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435    0.1602   -5.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)
  Mrv1652309122123022D          

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M  END
> <DATABASE_ID>
HMDB0272160

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C48H87O12P/c1-4-5-25-32-43(50)33-27-22-18-16-19-23-28-34-44(51)35-30-37-47(53)57-40-46(41-59-61(55,56)58-39-45(52)38-49)60-48(54)36-29-24-20-15-13-11-9-7-6-8-10-12-14-17-21-26-31-42(2)3/h18-19,22-23,27-28,33-34,42-46,49-52H,4-17,20-21,24-26,29-32,35-41H2,1-3H3,(H,55,56)/b22-18-,23-19-,33-27+,34-28+/t43-,44-,45-,46+/m0/s1

> <INCHI_KEY>
OZDSJTDDUHQULY-QDRHCDRTSA-N

> <FORMULA>
C48H87O12P

> <MOLECULAR_WEIGHT>
887.186

> <EXACT_MASS>
886.593515239

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
106.02494311058081

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-{[(5R,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
7.65

> <JCHEM_LOGP>
11.315879840000001

> <ALOGPS_LOGS>
-6.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.641245576372423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8910809700487992

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2596748605453434

> <JCHEM_POLAR_SURFACE_AREA>
189.28

> <JCHEM_REFRACTIVITY>
248.7639000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
45

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(5R,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0272160
     RDKit          3D
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)
148147  0  0  0  0  0  0  0  0999 V2000
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 60144  1  0
 60145  1  0
 61146  1  0
 61147  1  0
 61148  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)        
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  O   UNK     0     -13.755   2.876   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -19.294   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -20.627   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.960   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -23.500   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -24.833   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -26.166   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -27.499   1.436   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -27.499   2.876   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -28.832   0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -30.165   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -31.498   0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -32.831   1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -34.164   0.665   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  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
HETATM   62  C   UNK     0     -33.211  -1.433   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -33.211   0.106   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   41                                                       
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   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   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   17   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                                                       
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   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  124    0
END

COMPND    HMDB0272160
HETATM    1  C1  UNL     1      -2.465   8.084  -1.656  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.447   8.242  -0.144  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.896   7.060   0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.662   5.783   0.328  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.091   5.894   0.754  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.873   4.637   0.528  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.334   3.564   1.235  1.00  0.00           O  
HETATM    8  C7  UNL     1      -4.946   4.286  -0.921  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.316   3.042  -1.283  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.399   2.660  -2.668  1.00  0.00           C  
HETATM   11  C10 UNL     1      -5.768   1.453  -3.035  1.00  0.00           C  
HETATM   12  C11 UNL     1      -6.118   0.417  -2.126  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.415  -0.840  -1.992  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.361  -1.220  -2.626  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.647  -0.455  -3.616  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.563  -1.016  -4.202  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.761  -0.320  -5.229  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.995  -1.269  -5.882  1.00  0.00           O  
HETATM   19  C17 UNL     1      -0.849   0.727  -4.632  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.023   1.388  -5.713  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.883   2.462  -5.244  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.874   2.095  -4.223  1.00  0.00           C  
HETATM   23  O3  UNL     1       1.717   2.486  -3.018  1.00  0.00           O  
HETATM   24  O4  UNL     1       3.000   1.338  -4.477  1.00  0.00           O  
HETATM   25  C21 UNL     1       3.957   1.009  -3.514  1.00  0.00           C  
HETATM   26  C22 UNL     1       3.538   0.263  -2.323  1.00  0.00           C  
HETATM   27  C23 UNL     1       4.785   0.143  -1.420  1.00  0.00           C  
HETATM   28  O5  UNL     1       4.402  -0.352  -0.172  1.00  0.00           O  
HETATM   29  P1  UNL     1       5.763  -0.499   0.784  1.00  0.00           P  
HETATM   30  O6  UNL     1       5.425  -0.359   2.259  1.00  0.00           O  
HETATM   31  O7  UNL     1       6.849   0.720   0.342  1.00  0.00           O  
HETATM   32  O8  UNL     1       6.424  -2.034   0.497  1.00  0.00           O  
HETATM   33  C24 UNL     1       5.583  -2.976   1.063  1.00  0.00           C  
HETATM   34  C25 UNL     1       6.104  -4.386   0.856  1.00  0.00           C  
HETATM   35  O9  UNL     1       7.368  -4.453   1.463  1.00  0.00           O  
HETATM   36  C26 UNL     1       5.193  -5.314   1.634  1.00  0.00           C  
HETATM   37  O10 UNL     1       5.647  -6.636   1.617  1.00  0.00           O  
HETATM   38  O11 UNL     1       3.016  -1.000  -2.416  1.00  0.00           O  
HETATM   39  C27 UNL     1       1.827  -1.506  -2.008  1.00  0.00           C  
HETATM   40  O12 UNL     1       1.013  -0.724  -1.465  1.00  0.00           O  
HETATM   41  C28 UNL     1       1.450  -2.921  -2.167  1.00  0.00           C  
HETATM   42  C29 UNL     1       0.061  -3.089  -2.679  1.00  0.00           C  
HETATM   43  C30 UNL     1      -0.317  -4.553  -2.802  1.00  0.00           C  
HETATM   44  C31 UNL     1      -0.343  -5.251  -1.439  1.00  0.00           C  
HETATM   45  C32 UNL     1      -1.418  -4.619  -0.606  1.00  0.00           C  
HETATM   46  C33 UNL     1      -1.547  -5.195   0.785  1.00  0.00           C  
HETATM   47  C34 UNL     1      -0.271  -4.915   1.531  1.00  0.00           C  
HETATM   48  C35 UNL     1      -0.259  -5.461   2.939  1.00  0.00           C  
HETATM   49  C36 UNL     1       1.006  -5.110   3.670  1.00  0.00           C  
HETATM   50  C37 UNL     1       1.202  -3.595   3.810  1.00  0.00           C  
HETATM   51  C38 UNL     1       0.071  -3.053   4.585  1.00  0.00           C  
HETATM   52  C39 UNL     1       0.041  -1.583   4.834  1.00  0.00           C  
HETATM   53  C40 UNL     1       1.194  -0.999   5.544  1.00  0.00           C  
HETATM   54  C41 UNL     1       1.117   0.463   5.810  1.00  0.00           C  
HETATM   55  C42 UNL     1       0.969   1.345   4.622  1.00  0.00           C  
HETATM   56  C43 UNL     1       2.105   1.219   3.649  1.00  0.00           C  
HETATM   57  C44 UNL     1       2.021   2.085   2.446  1.00  0.00           C  
HETATM   58  C45 UNL     1       0.790   1.806   1.649  1.00  0.00           C  
HETATM   59  C46 UNL     1       0.693   2.659   0.401  1.00  0.00           C  
HETATM   60  C47 UNL     1       0.675   4.123   0.770  1.00  0.00           C  
HETATM   61  C48 UNL     1      -0.599   2.317  -0.315  1.00  0.00           C  
HETATM   62  H1  UNL     1      -2.444   9.106  -2.083  1.00  0.00           H  
HETATM   63  H2  UNL     1      -1.594   7.548  -2.040  1.00  0.00           H  
HETATM   64  H3  UNL     1      -3.440   7.643  -1.911  1.00  0.00           H  
HETATM   65  H4  UNL     1      -1.765   9.101   0.057  1.00  0.00           H  
HETATM   66  H5  UNL     1      -3.470   8.518   0.183  1.00  0.00           H  
HETATM   67  H6  UNL     1      -1.988   7.278   1.667  1.00  0.00           H  
HETATM   68  H7  UNL     1      -0.829   6.950   0.350  1.00  0.00           H  
HETATM   69  H8  UNL     1      -2.663   5.477  -0.734  1.00  0.00           H  
HETATM   70  H9  UNL     1      -2.163   4.973   0.895  1.00  0.00           H  
HETATM   71  H10 UNL     1      -4.173   6.117   1.853  1.00  0.00           H  
HETATM   72  H11 UNL     1      -4.608   6.720   0.225  1.00  0.00           H  
HETATM   73  H12 UNL     1      -5.922   4.804   0.856  1.00  0.00           H  
HETATM   74  H13 UNL     1      -4.382   3.771   2.211  1.00  0.00           H  
HETATM   75  H14 UNL     1      -4.722   4.968  -1.707  1.00  0.00           H  
HETATM   76  H15 UNL     1      -5.529   2.382  -0.461  1.00  0.00           H  
HETATM   77  H16 UNL     1      -5.145   3.410  -3.426  1.00  0.00           H  
HETATM   78  H17 UNL     1      -5.841   1.309  -4.142  1.00  0.00           H  
HETATM   79  H18 UNL     1      -6.278   0.783  -1.051  1.00  0.00           H  
HETATM   80  H19 UNL     1      -7.249   0.179  -2.371  1.00  0.00           H  
HETATM   81  H20 UNL     1      -5.834  -1.579  -1.243  1.00  0.00           H  
HETATM   82  H21 UNL     1      -3.983  -2.236  -2.368  1.00  0.00           H  
HETATM   83  H22 UNL     1      -3.836   0.524  -3.950  1.00  0.00           H  
HETATM   84  H23 UNL     1      -2.313  -2.027  -3.872  1.00  0.00           H  
HETATM   85  H24 UNL     1      -2.444   0.160  -5.988  1.00  0.00           H  
HETATM   86  H25 UNL     1      -0.072  -1.204  -5.560  1.00  0.00           H  
HETATM   87  H26 UNL     1      -1.491   1.489  -4.109  1.00  0.00           H  
HETATM   88  H27 UNL     1      -0.220   0.240  -3.875  1.00  0.00           H  
HETATM   89  H28 UNL     1       0.515   0.586  -6.266  1.00  0.00           H  
HETATM   90  H29 UNL     1      -0.771   1.802  -6.455  1.00  0.00           H  
HETATM   91  H30 UNL     1       1.481   2.820  -6.134  1.00  0.00           H  
HETATM   92  H31 UNL     1       0.291   3.363  -4.950  1.00  0.00           H  
HETATM   93  H32 UNL     1       4.894   0.588  -3.991  1.00  0.00           H  
HETATM   94  H33 UNL     1       4.337   2.013  -3.137  1.00  0.00           H  
HETATM   95  H34 UNL     1       2.857   0.968  -1.740  1.00  0.00           H  
HETATM   96  H35 UNL     1       5.165   1.172  -1.258  1.00  0.00           H  
HETATM   97  H36 UNL     1       5.567  -0.446  -1.917  1.00  0.00           H  
HETATM   98  H37 UNL     1       6.369   1.582   0.415  1.00  0.00           H  
HETATM   99  H38 UNL     1       4.547  -2.889   0.701  1.00  0.00           H  
HETATM  100  H39 UNL     1       5.560  -2.783   2.166  1.00  0.00           H  
HETATM  101  H40 UNL     1       6.143  -4.645  -0.218  1.00  0.00           H  
HETATM  102  H41 UNL     1       7.974  -3.755   1.100  1.00  0.00           H  
HETATM  103  H42 UNL     1       5.194  -4.947   2.683  1.00  0.00           H  
HETATM  104  H43 UNL     1       4.144  -5.261   1.257  1.00  0.00           H  
HETATM  105  H44 UNL     1       5.147  -7.177   0.980  1.00  0.00           H  
HETATM  106  H45 UNL     1       2.164  -3.368  -2.921  1.00  0.00           H  
HETATM  107  H46 UNL     1       1.592  -3.406  -1.170  1.00  0.00           H  
HETATM  108  H47 UNL     1       0.049  -2.702  -3.728  1.00  0.00           H  
HETATM  109  H48 UNL     1      -0.715  -2.557  -2.139  1.00  0.00           H  
HETATM  110  H49 UNL     1       0.353  -5.088  -3.495  1.00  0.00           H  
HETATM  111  H50 UNL     1      -1.346  -4.592  -3.206  1.00  0.00           H  
HETATM  112  H51 UNL     1       0.671  -5.170  -1.020  1.00  0.00           H  
HETATM  113  H52 UNL     1      -0.526  -6.336  -1.600  1.00  0.00           H  
HETATM  114  H53 UNL     1      -1.083  -3.554  -0.439  1.00  0.00           H  
HETATM  115  H54 UNL     1      -2.379  -4.529  -1.139  1.00  0.00           H  
HETATM  116  H55 UNL     1      -2.340  -4.564   1.286  1.00  0.00           H  
HETATM  117  H56 UNL     1      -1.838  -6.250   0.798  1.00  0.00           H  
HETATM  118  H57 UNL     1       0.542  -5.433   0.974  1.00  0.00           H  
HETATM  119  H58 UNL     1      -0.055  -3.831   1.579  1.00  0.00           H  
HETATM  120  H59 UNL     1      -0.230  -6.592   2.838  1.00  0.00           H  
HETATM  121  H60 UNL     1      -1.145  -5.233   3.524  1.00  0.00           H  
HETATM  122  H61 UNL     1       1.906  -5.504   3.154  1.00  0.00           H  
HETATM  123  H62 UNL     1       0.920  -5.486   4.706  1.00  0.00           H  
HETATM  124  H63 UNL     1       1.375  -3.209   2.812  1.00  0.00           H  
HETATM  125  H64 UNL     1       2.137  -3.463   4.400  1.00  0.00           H  
HETATM  126  H65 UNL     1      -0.891  -3.368   4.079  1.00  0.00           H  
HETATM  127  H66 UNL     1       0.038  -3.622   5.564  1.00  0.00           H  
HETATM  128  H67 UNL     1      -0.193  -1.103   3.860  1.00  0.00           H  
HETATM  129  H68 UNL     1      -0.892  -1.404   5.456  1.00  0.00           H  
HETATM  130  H69 UNL     1       1.337  -1.523   6.508  1.00  0.00           H  
HETATM  131  H70 UNL     1       2.129  -1.230   4.954  1.00  0.00           H  
HETATM  132  H71 UNL     1       2.036   0.779   6.353  1.00  0.00           H  
HETATM  133  H72 UNL     1       0.284   0.699   6.514  1.00  0.00           H  
HETATM  134  H73 UNL     1      -0.026   1.249   4.130  1.00  0.00           H  
HETATM  135  H74 UNL     1       0.993   2.401   4.993  1.00  0.00           H  
HETATM  136  H75 UNL     1       3.043   1.484   4.226  1.00  0.00           H  
HETATM  137  H76 UNL     1       2.267   0.179   3.304  1.00  0.00           H  
HETATM  138  H77 UNL     1       2.150   3.171   2.668  1.00  0.00           H  
HETATM  139  H78 UNL     1       2.900   1.811   1.794  1.00  0.00           H  
HETATM  140  H79 UNL     1      -0.103   2.024   2.300  1.00  0.00           H  
HETATM  141  H80 UNL     1       0.777   0.742   1.339  1.00  0.00           H  
HETATM  142  H81 UNL     1       1.576   2.466  -0.219  1.00  0.00           H  
HETATM  143  H82 UNL     1       1.718   4.506   0.893  1.00  0.00           H  
HETATM  144  H83 UNL     1       0.241   4.695  -0.081  1.00  0.00           H  
HETATM  145  H84 UNL     1       0.135   4.275   1.713  1.00  0.00           H  
HETATM  146  H85 UNL     1      -0.594   1.363  -0.837  1.00  0.00           H  
HETATM  147  H86 UNL     1      -0.784   3.093  -1.104  1.00  0.00           H  
HETATM  148  H87 UNL     1      -1.456   2.334   0.391  1.00  0.00           H  
CONECT    1    2   62   63   64
CONECT    2    3   65   66
CONECT    3    4   67   68
CONECT    4    5   69   70
CONECT    5    6   71   72
CONECT    6    7    8   73
CONECT    7   74
CONECT    8    9    9   75
CONECT    9   10   76
CONECT   10   11   11   77
CONECT   11   12   78
CONECT   12   13   79   80
CONECT   13   14   14   81
CONECT   14   15   82
CONECT   15   16   16   83
CONECT   16   17   84
CONECT   17   18   19   85
CONECT   18   86
CONECT   19   20   87   88
CONECT   20   21   89   90
CONECT   21   22   91   92
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   93   94
CONECT   26   27   38   95
CONECT   27   28   96   97
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   98
CONECT   32   33
CONECT   33   34   99  100
CONECT   34   35   36  101
CONECT   35  102
CONECT   36   37  103  104
CONECT   37  105
CONECT   38   39
CONECT   39   40   40   41
CONECT   41   42  106  107
CONECT   42   43  108  109
CONECT   43   44  110  111
CONECT   44   45  112  113
CONECT   45   46  114  115
CONECT   46   47  116  117
CONECT   47   48  118  119
CONECT   48   49  120  121
CONECT   49   50  122  123
CONECT   50   51  124  125
CONECT   51   52  126  127
CONECT   52   53  128  129
CONECT   53   54  130  131
CONECT   54   55  132  133
CONECT   55   56  134  135
CONECT   56   57  136  137
CONECT   57   58  138  139
CONECT   58   59  140  141
CONECT   59   60   61  142
CONECT   60  143  144  145
CONECT   61  146  147  148
END

HMDB0272160
     RDKit          3D
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)
148147  0  0  0  0  0  0  0  0999 V2000
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    6.1036   -4.3858    0.8556 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3682   -4.4534    1.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -5.3138    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -6.6361    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0158   -0.9999   -2.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0128   -0.7236   -1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0614   -3.0892   -2.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4181   -4.6188   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2710   -4.9148    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585   -5.4606    2.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -5.1102    3.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2836    0.6992    6.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9930    2.4005    4.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0432    1.4838    4.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2671    0.1789    3.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1503    3.1709    2.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996    1.8107    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    2.0240    2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771    0.7422    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761    2.4662   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177    4.5063    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2411    4.6947   -0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    4.2750    1.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942    1.3632   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837    3.0933   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557    2.3337    0.3906 H   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
[(2R)-3-{[(5R,6E,8Z,11Z,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinate	Generator

Chemical Formula

C₄₈H₈₇O₁₂P

Average Molecular Weight

887.186

Monoisotopic Molecular Weight

886.593515239

IUPAC Name

[(2R)-3-{[(5R,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid

Traditional Name

(2R)-3-{[(5R,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C48H87O12P/c1-4-5-25-32-43(50)33-27-22-18-16-19-23-28-34-44(51)35-30-37-47(53)57-40-46(41-59-61(55,56)58-39-45(52)38-49)60-48(54)36-29-24-20-15-13-11-9-7-6-8-10-12-14-17-21-26-31-42(2)3/h18-19,22-23,27-28,33-34,42-46,49-52H,4-17,20-21,24-26,29-32,35-41H2,1-3H3,(H,55,56)/b22-18-,23-19-,33-27+,34-28+/t43-,44-,45-,46+/m0/s1

InChI Key

OZDSJTDDUHQULY-QDRHCDRTSA-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	7.65	ALOGPS
logP	11.32	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	45	ChemAxon
Refractivity	248.76 m³·mol⁻¹	ChemAxon
Polarizability	106.02 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]+	305.402	32859911
AllCCS	[M+H-H2O]+	305.515	32859911
AllCCS	[M+Na]+	305.224	32859911
AllCCS	[M+NH4]+	305.268	32859911
AllCCS	[M-H]-	303.885	32859911
AllCCS	[M+Na-2H]-	310.776	32859911
AllCCS	[M+HCOO]-	318.31	32859911
DeepCCS	[M+H]+	301.415	30932474
DeepCCS	[M-H]-	299.52	30932474
DeepCCS	[M-2H]-	333.256	30932474
DeepCCS	[M+Na]+	307.271	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C	6165.7	Standard polar	33892256
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C	5118.0	Standard non polar	33892256
PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C	6410.4	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(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0) 10V, Negative-QTOF	splash10-000i-0000000090-487599c21383e3b66643	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0) 20V, Negative-QTOF	splash10-000i-0009130040-f8b56ce7ab8d9a352501	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0) 40V, Negative-QTOF	splash10-000i-0109130040-98aa7704411fc4b13061	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(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0) (HMDB0272160)

MOL for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

3D MOL for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

3D SDF for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

3D-SDF for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

PDB for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

3D PDB for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

SMILES for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

INCHI for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

Structure for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

3D Structure for HMDB0272160 (PG(20:4(6E,8Z,11Z,13E)-2OH(5S,15S)/i-22:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra