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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-13 04:04:27 UTC

Update Date

2022-11-30 20:00:23 UTC

HMDB ID

HMDB0275667

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PGP(18:2(9Z,11E)+=O(13)/i-20:0)

Description

PGP(18:2(9Z,11E)+=O(13)/i-20:0) is an oxidized phosphoglycerophosphate (PGP). Oxidized phosphoglycerophosphates are glycerophospholipids in which a phosphoglycerol moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphoglycerophosphates belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphoglycerophosphates can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PGP(18:2(9Z,11E)+=O(13)/i-20:0), in particular, consists of one chain of one 13-oxo-octadecadienoyl at the C-1 position and one chain of 18-methylnonadecanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PGPs can be synthesized via three different routes. In one route, the oxidized PGP is synthetized de novo following the same mechanisms as for PGPs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PGP backbone, mainely through the action of LOX (PMID: 33329396 ).

Structure

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

PGP(18:2(9Z,11E)+=O(13)/i-20:0)
  Mrv1652309132106042D          

 62 61  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    1.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6134    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7177    0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.8108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156    1.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.8990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -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
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6518   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  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
  -16.3636    0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 19  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8 16  1  0  0  0  0
  8 15  1  6  0  0  0
  9  8  1  0  0  0  0
  9 14  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 19 18  1  0  0  0  0
 21 42  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 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
 40 41  1  0  0  0  0
 42 43  2  0  0  0  0
 42 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
 60 62  1  0  0  0  0
M  END

HMDB0275667
     RDKit          3D
PGP(18:2(9Z,11E)+=O(13)/i-20:0)
142141  0  0  0  0  0  0  0  0999 V2000
   -6.6251    3.3704    1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8825    4.4190    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402    4.0489    2.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8539    5.2035    3.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    4.8520    3.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7661    5.9246    4.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466    7.0109    4.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416    5.9215    4.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    4.9496    4.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381    5.1239    5.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    4.2302    5.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616    2.9265    4.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636    1.8908    5.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7661    0.4649    5.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0840    0.2463    4.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4389   -1.1266    4.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -1.9804    3.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062   -1.4550    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -2.4372    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -3.2254    1.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5895   -2.5050   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922   -3.3497   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820   -3.4373   -1.6299 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7384   -4.5894   -2.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -4.9116   -2.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4092   -6.1664   -4.1142 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0209   -6.6663   -4.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -7.4755   -3.6045 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -5.7068   -5.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -5.5568   -6.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313   -5.1564   -7.8983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2908   -5.0007   -8.9103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -3.8482   -7.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -3.4759   -8.8997 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041   -2.0097   -8.5976 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.1452   -2.2572   -7.9222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8039   -1.0418   -7.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.1669  -10.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1727   -2.3049   -2.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790   -1.8906   -1.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -2.5892   -0.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307   -0.6628   -2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431   -1.0729   -3.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9372   -1.8114   -2.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -1.0064   -1.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0653   -1.8150   -1.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8780   -2.9846   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5929   -2.8342    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -1.9167    1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2408   -2.0591    2.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1923   -1.2602    3.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.1895    3.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    1.1105    2.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.1696    1.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    2.2252    0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    2.4134   -0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    2.9007    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    3.0735   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122    1.7825   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451    3.5523    0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9671    2.8680    0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0722    2.6125    2.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5050    3.8459    0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    5.3804    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3877    4.5740    3.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264    3.8650    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4684    3.1344    3.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219    6.1346    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3428    5.3241    4.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8768    4.7130    2.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    3.9518    4.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1176    6.7944    5.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    4.0704    4.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9441    6.0820    6.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    4.4508    6.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7178    2.8215    4.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    2.8872    4.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    2.0135    6.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    2.1940    6.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927   -0.1464    6.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094    0.1707    4.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8620    0.6447    5.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959    0.9548    3.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540   -1.0730    4.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033   -1.6783    5.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -3.0150    3.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -2.1274    3.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8799   -1.3630    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -0.4636    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491   -4.4154   -1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
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 60142  1  0
M  END

PGP(18:2(9Z,11E)+=O(13)/i-20:0)
  Mrv1652309132106042D          

 62 61  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
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  1 22  1  0  0  0  0
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  3  2  1  0  0  0  0
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 11 10  1  0  0  0  0
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 17  1  1  0  0  0  0
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 49 50  1  0  0  0  0
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 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0275667

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H82O14P2/c1-4-5-25-31-40(45)32-27-22-18-14-12-16-19-23-28-33-43(47)54-37-42(38-57-60(52,53)56-36-41(46)35-55-59(49,50)51)58-44(48)34-29-24-20-15-11-9-7-6-8-10-13-17-21-26-30-39(2)3/h18,22,27,32,39,41-42,46H,4-17,19-21,23-26,28-31,33-38H2,1-3H3,(H,52,53)(H2,49,50,51)/b22-18-,32-27+/t41-,42+/m0/s1

> <INCHI_KEY>
KYXUDHIRPSOWEA-AVRZSEDTSA-N

> <FORMULA>
C44H82O14P2

> <MOLECULAR_WEIGHT>
897.074

> <EXACT_MASS>
896.517981316

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
142

> <JCHEM_AVERAGE_POLARIZABILITY>
102.43196479121315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(18-methylnonadecanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphoryl}oxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
7.16

> <JCHEM_LOGP>
11.780032017

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.0402062485298225

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3548796995413768

> <JCHEM_PKA_STRONGEST_BASIC>
-3.410499386302644

> <JCHEM_POLAR_SURFACE_AREA>
212.42

> <JCHEM_REFRACTIVITY>
236.58670000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
45

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(18-methylnonadecanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy)phosphoryl]oxy}propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0275667
     RDKit          3D
PGP(18:2(9Z,11E)+=O(13)/i-20:0)
142141  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 13-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(18:2(9Z,11E)+=O(13)/i-20:0)                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-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       8.806   0.743   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       7.473   1.513   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0       8.242   2.848   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.702   0.180   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.138   2.284   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       4.315   3.545   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0       2.775   3.545   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.627   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -21.960   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -24.626  -0.775   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -22.547  -1.433   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -23.880  -0.662   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -25.213  -1.433   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -26.546  -0.662   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -27.879  -1.433   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -29.212  -0.662   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -30.545  -1.433   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -30.545   0.106   0.000  0.00  0.00           C+0
CONECT    1   22   17                                                       
CONECT    2   19    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   16   15    9                                             
CONECT    9    8   14                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   11                                                       
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    1   18                                                       
CONECT   18   17   20   21   19                                             
CONECT   19    2   18                                                       
CONECT   20   18                                                            
CONECT   21   18   42                                                       
CONECT   22    1   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   21   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   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   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  122    0
END

COMPND    HMDB0275667
HETATM    1  C1  UNL     1      -6.625   3.370   1.497  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.883   4.419   2.261  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.440   4.049   2.559  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.854   5.204   3.326  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.398   4.852   3.656  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.766   5.925   4.417  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.447   7.011   4.637  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.442   5.922   4.975  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.457   4.950   4.885  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.738   5.124   5.516  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.677   4.230   5.485  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.562   2.927   4.803  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.664   1.891   5.866  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.766   0.465   5.479  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.084   0.246   4.756  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.439  -1.127   4.429  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.712  -1.980   3.492  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.806  -1.455   2.076  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.207  -2.437   1.117  1.00  0.00           C  
HETATM   20  O2  UNL     1       2.344  -3.225   1.520  1.00  0.00           O  
HETATM   21  O3  UNL     1       3.590  -2.505  -0.204  1.00  0.00           O  
HETATM   22  C19 UNL     1       3.192  -3.350  -1.203  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.782  -3.437  -1.630  1.00  0.00           C  
HETATM   24  C21 UNL     1       1.738  -4.589  -2.658  1.00  0.00           C  
HETATM   25  O4  UNL     1       0.421  -4.912  -2.980  1.00  0.00           O  
HETATM   26  P1  UNL     1       0.409  -6.166  -4.114  1.00  0.00           P  
HETATM   27  O5  UNL     1      -1.021  -6.666  -4.249  1.00  0.00           O  
HETATM   28  O6  UNL     1       1.356  -7.475  -3.605  1.00  0.00           O  
HETATM   29  O7  UNL     1       0.952  -5.707  -5.622  1.00  0.00           O  
HETATM   30  C22 UNL     1      -0.017  -5.557  -6.583  1.00  0.00           C  
HETATM   31  C23 UNL     1       0.631  -5.156  -7.898  1.00  0.00           C  
HETATM   32  O8  UNL     1      -0.291  -5.001  -8.910  1.00  0.00           O  
HETATM   33  C24 UNL     1       1.363  -3.848  -7.728  1.00  0.00           C  
HETATM   34  O9  UNL     1       2.030  -3.476  -8.900  1.00  0.00           O  
HETATM   35  P2  UNL     1       2.804  -2.010  -8.598  1.00  0.00           P  
HETATM   36  O10 UNL     1       4.145  -2.257  -7.922  1.00  0.00           O  
HETATM   37  O11 UNL     1       1.804  -1.042  -7.654  1.00  0.00           O  
HETATM   38  O12 UNL     1       3.131  -1.167 -10.017  1.00  0.00           O  
HETATM   39  O13 UNL     1       1.173  -2.305  -2.133  1.00  0.00           O  
HETATM   40  C25 UNL     1      -0.079  -1.891  -1.653  1.00  0.00           C  
HETATM   41  O14 UNL     1      -0.555  -2.589  -0.779  1.00  0.00           O  
HETATM   42  C26 UNL     1      -0.731  -0.663  -2.227  1.00  0.00           C  
HETATM   43  C27 UNL     1      -1.743  -1.073  -3.224  1.00  0.00           C  
HETATM   44  C28 UNL     1      -2.937  -1.811  -2.770  1.00  0.00           C  
HETATM   45  C29 UNL     1      -3.886  -1.006  -1.878  1.00  0.00           C  
HETATM   46  C30 UNL     1      -5.065  -1.815  -1.476  1.00  0.00           C  
HETATM   47  C31 UNL     1      -4.878  -2.985  -0.611  1.00  0.00           C  
HETATM   48  C32 UNL     1      -4.593  -2.834   0.827  1.00  0.00           C  
HETATM   49  C33 UNL     1      -3.457  -1.917   1.206  1.00  0.00           C  
HETATM   50  C34 UNL     1      -3.241  -2.059   2.675  1.00  0.00           C  
HETATM   51  C35 UNL     1      -2.192  -1.260   3.347  1.00  0.00           C  
HETATM   52  C36 UNL     1      -2.268   0.190   3.417  1.00  0.00           C  
HETATM   53  C37 UNL     1      -2.200   1.111   2.298  1.00  0.00           C  
HETATM   54  C38 UNL     1      -0.920   1.170   1.495  1.00  0.00           C  
HETATM   55  C39 UNL     1      -1.043   2.225   0.399  1.00  0.00           C  
HETATM   56  C40 UNL     1       0.209   2.413  -0.394  1.00  0.00           C  
HETATM   57  C41 UNL     1       1.382   2.901   0.444  1.00  0.00           C  
HETATM   58  C42 UNL     1       2.612   3.073  -0.427  1.00  0.00           C  
HETATM   59  C43 UNL     1       3.012   1.783  -1.082  1.00  0.00           C  
HETATM   60  C44 UNL     1       3.745   3.552   0.436  1.00  0.00           C  
HETATM   61  H1  UNL     1      -5.967   2.868   0.767  1.00  0.00           H  
HETATM   62  H2  UNL     1      -7.072   2.613   2.197  1.00  0.00           H  
HETATM   63  H3  UNL     1      -7.505   3.846   0.998  1.00  0.00           H  
HETATM   64  H4  UNL     1      -5.935   5.380   1.705  1.00  0.00           H  
HETATM   65  H5  UNL     1      -6.388   4.574   3.248  1.00  0.00           H  
HETATM   66  H6  UNL     1      -3.926   3.865   1.606  1.00  0.00           H  
HETATM   67  H7  UNL     1      -4.468   3.134   3.197  1.00  0.00           H  
HETATM   68  H8  UNL     1      -3.922   6.135   2.726  1.00  0.00           H  
HETATM   69  H9  UNL     1      -4.343   5.324   4.314  1.00  0.00           H  
HETATM   70  H10 UNL     1      -1.877   4.713   2.706  1.00  0.00           H  
HETATM   71  H11 UNL     1      -2.448   3.952   4.298  1.00  0.00           H  
HETATM   72  H12 UNL     1      -0.118   6.794   5.536  1.00  0.00           H  
HETATM   73  H13 UNL     1       0.206   4.070   4.350  1.00  0.00           H  
HETATM   74  H14 UNL     1       1.944   6.082   6.063  1.00  0.00           H  
HETATM   75  H15 UNL     1       3.653   4.451   6.011  1.00  0.00           H  
HETATM   76  H16 UNL     1       1.718   2.822   4.129  1.00  0.00           H  
HETATM   77  H17 UNL     1       3.474   2.887   4.116  1.00  0.00           H  
HETATM   78  H18 UNL     1       1.758   2.014   6.521  1.00  0.00           H  
HETATM   79  H19 UNL     1       3.516   2.194   6.530  1.00  0.00           H  
HETATM   80  H20 UNL     1       2.793  -0.146   6.400  1.00  0.00           H  
HETATM   81  H21 UNL     1       1.909   0.171   4.868  1.00  0.00           H  
HETATM   82  H22 UNL     1       4.862   0.645   5.470  1.00  0.00           H  
HETATM   83  H23 UNL     1       4.096   0.955   3.898  1.00  0.00           H  
HETATM   84  H24 UNL     1       5.554  -1.073   4.094  1.00  0.00           H  
HETATM   85  H25 UNL     1       4.603  -1.678   5.431  1.00  0.00           H  
HETATM   86  H26 UNL     1       4.157  -3.015   3.542  1.00  0.00           H  
HETATM   87  H27 UNL     1       2.659  -2.127   3.814  1.00  0.00           H  
HETATM   88  H28 UNL     1       4.880  -1.363   1.827  1.00  0.00           H  
HETATM   89  H29 UNL     1       3.357  -0.464   2.035  1.00  0.00           H  
HETATM   90  H30 UNL     1       3.549  -4.415  -1.047  1.00  0.00           H  
HETATM   91  H31 UNL     1       3.789  -3.038  -2.134  1.00  0.00           H  
HETATM   92  H32 UNL     1       1.158  -3.848  -0.795  1.00  0.00           H  
HETATM   93  H33 UNL     1       2.394  -4.404  -3.512  1.00  0.00           H  
HETATM   94  H34 UNL     1       2.150  -5.459  -2.110  1.00  0.00           H  
HETATM   95  H35 UNL     1       2.266  -7.402  -4.020  1.00  0.00           H  
HETATM   96  H36 UNL     1      -0.647  -6.460  -6.758  1.00  0.00           H  
HETATM   97  H37 UNL     1      -0.747  -4.757  -6.314  1.00  0.00           H  
HETATM   98  H38 UNL     1       1.325  -5.975  -8.198  1.00  0.00           H  
HETATM   99  H39 UNL     1      -1.082  -4.464  -8.658  1.00  0.00           H  
HETATM  100  H40 UNL     1       0.620  -3.058  -7.540  1.00  0.00           H  
HETATM  101  H41 UNL     1       2.137  -3.913  -6.936  1.00  0.00           H  
HETATM  102  H42 UNL     1       2.332  -0.675  -6.911  1.00  0.00           H  
HETATM  103  H43 UNL     1       3.345  -0.241  -9.752  1.00  0.00           H  
HETATM  104  H44 UNL     1      -1.138  -0.036  -1.404  1.00  0.00           H  
HETATM  105  H45 UNL     1       0.069  -0.087  -2.727  1.00  0.00           H  
HETATM  106  H46 UNL     1      -2.065  -0.219  -3.868  1.00  0.00           H  
HETATM  107  H47 UNL     1      -1.208  -1.761  -3.952  1.00  0.00           H  
HETATM  108  H48 UNL     1      -2.713  -2.796  -2.313  1.00  0.00           H  
HETATM  109  H49 UNL     1      -3.544  -2.047  -3.684  1.00  0.00           H  
HETATM  110  H50 UNL     1      -3.404  -0.516  -1.059  1.00  0.00           H  
HETATM  111  H51 UNL     1      -4.306  -0.167  -2.523  1.00  0.00           H  
HETATM  112  H52 UNL     1      -5.632  -2.041  -2.423  1.00  0.00           H  
HETATM  113  H53 UNL     1      -5.761  -1.096  -0.936  1.00  0.00           H  
HETATM  114  H54 UNL     1      -4.100  -3.706  -1.011  1.00  0.00           H  
HETATM  115  H55 UNL     1      -5.854  -3.591  -0.708  1.00  0.00           H  
HETATM  116  H56 UNL     1      -4.261  -3.860   1.209  1.00  0.00           H  
HETATM  117  H57 UNL     1      -5.518  -2.578   1.428  1.00  0.00           H  
HETATM  118  H58 UNL     1      -3.899  -0.864   1.051  1.00  0.00           H  
HETATM  119  H59 UNL     1      -2.589  -2.105   0.618  1.00  0.00           H  
HETATM  120  H60 UNL     1      -4.202  -1.891   3.241  1.00  0.00           H  
HETATM  121  H61 UNL     1      -3.074  -3.181   2.842  1.00  0.00           H  
HETATM  122  H62 UNL     1      -2.213  -1.630   4.442  1.00  0.00           H  
HETATM  123  H63 UNL     1      -1.152  -1.634   3.052  1.00  0.00           H  
HETATM  124  H64 UNL     1      -1.571   0.511   4.277  1.00  0.00           H  
HETATM  125  H65 UNL     1      -3.284   0.419   3.935  1.00  0.00           H  
HETATM  126  H66 UNL     1      -3.098   1.129   1.664  1.00  0.00           H  
HETATM  127  H67 UNL     1      -2.235   2.168   2.774  1.00  0.00           H  
HETATM  128  H68 UNL     1      -0.042   1.395   2.082  1.00  0.00           H  
HETATM  129  H69 UNL     1      -0.825   0.193   0.982  1.00  0.00           H  
HETATM  130  H70 UNL     1      -1.910   1.926  -0.227  1.00  0.00           H  
HETATM  131  H71 UNL     1      -1.237   3.204   0.910  1.00  0.00           H  
HETATM  132  H72 UNL     1       0.067   3.190  -1.179  1.00  0.00           H  
HETATM  133  H73 UNL     1       0.558   1.493  -0.901  1.00  0.00           H  
HETATM  134  H74 UNL     1       1.160   3.898   0.883  1.00  0.00           H  
HETATM  135  H75 UNL     1       1.631   2.160   1.225  1.00  0.00           H  
HETATM  136  H76 UNL     1       2.386   3.855  -1.217  1.00  0.00           H  
HETATM  137  H77 UNL     1       2.361   1.643  -1.978  1.00  0.00           H  
HETATM  138  H78 UNL     1       2.783   0.946  -0.377  1.00  0.00           H  
HETATM  139  H79 UNL     1       4.085   1.755  -1.344  1.00  0.00           H  
HETATM  140  H80 UNL     1       4.459   2.724   0.619  1.00  0.00           H  
HETATM  141  H81 UNL     1       3.404   3.904   1.434  1.00  0.00           H  
HETATM  142  H82 UNL     1       4.298   4.409  -0.050  1.00  0.00           H  
CONECT    1    2   61   62   63
CONECT    2    3   64   65
CONECT    3    4   66   67
CONECT    4    5   68   69
CONECT    5    6   70   71
CONECT    6    7    7    8
CONECT    8    9    9   72
CONECT    9   10   73
CONECT   10   11   11   74
CONECT   11   12   75
CONECT   12   13   76   77
CONECT   13   14   78   79
CONECT   14   15   80   81
CONECT   15   16   82   83
CONECT   16   17   84   85
CONECT   17   18   86   87
CONECT   18   19   88   89
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   90   91
CONECT   23   24   39   92
CONECT   24   25   93   94
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   95
CONECT   29   30
CONECT   30   31   96   97
CONECT   31   32   33   98
CONECT   32   99
CONECT   33   34  100  101
CONECT   34   35
CONECT   35   36   36   37   38
CONECT   37  102
CONECT   38  103
CONECT   39   40
CONECT   40   41   41   42
CONECT   42   43  104  105
CONECT   43   44  106  107
CONECT   44   45  108  109
CONECT   45   46  110  111
CONECT   46   47  112  113
CONECT   47   48  114  115
CONECT   48   49  116  117
CONECT   49   50  118  119
CONECT   50   51  120  121
CONECT   51   52  122  123
CONECT   52   53  124  125
CONECT   53   54  126  127
CONECT   54   55  128  129
CONECT   55   56  130  131
CONECT   56   57  132  133
CONECT   57   58  134  135
CONECT   58   59   60  136
CONECT   59  137  138  139
CONECT   60  140  141  142
END

HMDB0275667
     RDKit          3D
PGP(18:2(9Z,11E)+=O(13)/i-20:0)
142141  0  0  0  0  0  0  0  0999 V2000
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 52125  1  0
 53126  1  0
 53127  1  0
 54128  1  0
 54129  1  0
 55130  1  0
 55131  1  0
 56132  1  0
 56133  1  0
 57134  1  0
 57135  1  0
 58136  1  0
 59137  1  0
 59138  1  0
 59139  1  0
 60140  1  0
 60141  1  0
 60142  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(18-methylnonadecanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphoryl}oxy)propoxy]phosphonate	Generator

Chemical Formula

C₄₄H₈₂O₁₄P₂

Average Molecular Weight

897.074

Monoisotopic Molecular Weight

896.517981316

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(18-methylnonadecanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphoryl}oxy)propoxy]phosphonic acid

Traditional Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(18-methylnonadecanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy)phosphoryl]oxy}propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H82O14P2/c1-4-5-25-31-40(45)32-27-22-18-14-12-16-19-23-28-33-43(47)54-37-42(38-57-60(52,53)56-36-41(46)35-55-59(49,50)51)58-44(48)34-29-24-20-15-11-9-7-6-8-10-13-17-21-26-30-39(2)3/h18,22,27,32,39,41-42,46H,4-17,19-21,23-26,28-31,33-38H2,1-3H3,(H,52,53)(H2,49,50,51)/b22-18-,32-27+/t41-,42+/m0/s1

InChI Key

KYXUDHIRPSOWEA-AVRZSEDTSA-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	7.16	ALOGPS
logP	11.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	212.42 Å²	ChemAxon
Rotatable Bond Count	45	ChemAxon
Refractivity	236.59 m³·mol⁻¹	ChemAxon
Polarizability	102.43 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]+	303.524	32859911
AllCCS	[M+H-H2O]+	303.692	32859911
AllCCS	[M+Na]+	303.275	32859911
AllCCS	[M+NH4]+	303.335	32859911
AllCCS	[M-H]-	298.824	32859911
AllCCS	[M+Na-2H]-	305.576	32859911
AllCCS	[M+HCOO]-	312.969	32859911
DeepCCS	[M+H]+	290.303	30932474
DeepCCS	[M-H]-	288.441	30932474
DeepCCS	[M-2H]-	321.679	30932474
DeepCCS	[M+Na]+	295.909	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(18:2(9Z,11E)+=O(13)/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C=C/C(=O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	5824.0	Standard polar	33892256
PGP(18:2(9Z,11E)+=O(13)/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C=C/C(=O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	5105.7	Standard non polar	33892256
PGP(18:2(9Z,11E)+=O(13)/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C=C/C(=O)CCCCC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	6180.7	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 10V, Positive-QTOF	splash10-0002-4120006980-111b12936353f3a6a8e1	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 20V, Positive-QTOF	splash10-0532-2300005900-e4d5da599af67b41b7f1	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 40V, Positive-QTOF	splash10-0v4i-3395231000-9ad2e501fdf30234b1ab	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 10V, Negative-QTOF	splash10-0002-0010000090-ae4efdeeea0cff0cd00e	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 20V, Negative-QTOF	splash10-0f6t-3091122040-05992b723e44bbfa2164	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,11E)+=O(13)/i-20:0) 40V, Negative-QTOF	splash10-0gdj-3091250000-9522088e7524211065c3	2021-10-19	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for PGP(18:2(9Z,11E)+=O(13)/i-20:0) (HMDB0275667)

MOL for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

3D MOL for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

3D SDF for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

3D-SDF for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

PDB for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

3D PDB for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

SMILES for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

INCHI for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

Structure for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

3D Structure for HMDB0275667 (PGP(18:2(9Z,11E)+=O(13)/i-20:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra