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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-13 00:57:24 UTC

Update Date

2022-11-30 19:59:39 UTC

HMDB ID

HMDB0274173

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Description

PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of one 18-Hydroxyeicosatetraenoyl at the C-1 position and one chain of 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  Mrv1652309132102572D          

 66 65  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
   -8.1936    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9077    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6218    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4468    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1609    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8750    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7000    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4141    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1282    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6673    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3815    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0956    0.3564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -17.0956   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.8097    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.5238    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
   -6.4768   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1910   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9051   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7301   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4442   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1583   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9833   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6974   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4115   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2365   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9506   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6647   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4897   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2039   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9180   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7430   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.4571   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.1712   -0.3549    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 44  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  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  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  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  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

HMDB0274173
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
140139  0  0  0  0  0  0  0  0999 V2000
   -4.5049   -7.9636   -2.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656   -8.5541   -3.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7006   -9.1394   -4.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -8.7751   -6.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109   -7.7100   -6.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -6.7108   -7.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434   -5.4545   -6.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5279   -4.8385   -5.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3178   -3.6931   -6.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1400   -2.4249   -5.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917   -2.1627   -4.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138   -1.1915   -5.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -0.0401   -4.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5680    0.3772   -3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045    0.4260   -2.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    1.4940   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    2.7905   -2.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046    3.3091   -0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    4.4364   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113    5.3470   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4694    5.6360    0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584    4.3619    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7354    3.3983    0.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    4.1126    2.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8671    2.8464    2.5437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7171    2.0970    3.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2356    0.7765    3.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466   -0.0877    2.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8980    0.3914    1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.4745    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -1.7682    1.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -1.2362    0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.6522   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -0.8986   -0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844    0.5996   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132    0.8727   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9086    1.4958   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151    1.9853   -2.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604    3.4139   -2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524    4.3425   -2.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561    4.1851   -2.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9421    4.8900   -2.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    5.6480   -1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    6.0506   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    5.6436    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    6.2445    1.9882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9828    5.9151    1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    5.9033    3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4790    6.4770    4.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    2.8586    3.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    1.5520    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458    1.4610    3.9075 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.4496    2.2717    3.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    2.1920    5.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1101    3.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -0.2689    4.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7463   -1.6996    4.7475 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9336   -1.7057    5.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8048   -2.6284    5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694   -2.7680    4.8536 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055   -3.8512    5.7323 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.3193   -5.1843    5.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666   -3.2753    7.3014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128   -3.9882    4.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215   -7.8506   -3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4101   -8.7213   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -7.0093   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0324   -9.3912   -3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1695   -7.7565   -3.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9892   -9.9485   -4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1858   -9.2704   -6.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4354   -7.3606   -5.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3547   -8.2139   -7.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849   -7.0240   -8.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -4.8124   -7.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205   -4.7341   -4.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3630   -5.6053   -5.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0771   -3.8972   -7.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811   -1.6820   -6.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4742   -1.9322   -3.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4475   -3.1140   -4.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  Mrv1652309132102572D          

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 65 66  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0274173

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C48H76O14P2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-21-24-27-30-33-36-39-48(52)62-46(43-61-64(56,57)60-41-45(50)40-59-63(53,54)55)42-58-47(51)38-35-32-29-26-23-20-18-17-19-22-25-28-31-34-37-44(49)4-2/h5-6,8-9,11-12,14-15,18-22,24,26,28-31,33,44-46,49-50H,3-4,7,10,13,16-17,23,25,27,32,34-43H2,1-2H3,(H,56,57)(H2,53,54,55)/b6-5-,9-8-,12-11-,15-14-,20-18-,22-19-,24-21-,29-26-,31-28-,33-30-/t44-,45-,46+/m0/s1

> <INCHI_KEY>
AAOBBDXYOCJDLG-WKMKHWRRSA-N

> <FORMULA>
C48H76O14P2

> <MOLECULAR_WEIGHT>
939.07

> <EXACT_MASS>
938.471031123

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
100.33706193152103

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-{[(5Z,8Z,11Z,14Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
6.76

> <JCHEM_LOGP>
10.25323704433333

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.0403926773962744

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3555958651152142

> <JCHEM_PKA_STRONGEST_BASIC>
-1.327614908955494

> <JCHEM_POLAR_SURFACE_AREA>
215.57999999999998

> <JCHEM_REFRACTIVITY>
265.0273000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-{[(5Z,8Z,11Z,14Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0274173
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
140139  0  0  0  0  0  0  0  0999 V2000
   -4.5049   -7.9636   -2.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656   -8.5541   -3.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7006   -9.1394   -4.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -8.7751   -6.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109   -7.7100   -6.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -6.7108   -7.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434   -5.4545   -6.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5279   -4.8385   -5.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3178   -3.6931   -6.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1400   -2.4249   -5.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917   -2.1627   -4.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138   -1.1915   -5.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -0.0401   -4.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5680    0.3772   -3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045    0.4260   -2.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    1.4940   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    2.7905   -2.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046    3.3091   -0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    4.4364   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113    5.3470   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4694    5.6360    0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584    4.3619    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7354    3.3983    0.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    4.1126    2.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8671    2.8464    2.5437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7171    2.0970    3.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2356    0.7765    3.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466   -0.0877    2.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8980    0.3914    1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.4745    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -1.7682    1.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -1.2362    0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.6522   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -0.8986   -0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844    0.5996   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132    0.8727   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9086    1.4958   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151    1.9853   -2.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604    3.4139   -2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524    4.3425   -2.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561    4.1851   -2.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9421    4.8900   -2.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    5.6480   -1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    6.0506   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    5.6436    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    6.2445    1.9882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9828    5.9151    1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    5.9033    3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4790    6.4770    4.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    2.8586    3.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    1.5520    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458    1.4610    3.9075 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.4496    2.2717    3.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    2.1920    5.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1101    3.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -0.2689    4.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7463   -1.6996    4.7475 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9336   -1.7057    5.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8048   -2.6284    5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694   -2.7680    4.8536 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055   -3.8512    5.7323 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.3193   -5.1843    5.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666   -3.2753    7.3014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128   -3.9882    4.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215   -7.8506   -3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4101   -8.7213   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -7.0093   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0324   -9.3912   -3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1695   -7.7565   -3.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9892   -9.9485   -4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1858   -9.2704   -6.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4354   -7.3606   -5.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3547   -8.2139   -7.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849   -7.0240   -8.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -4.8124   -7.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205   -4.7341   -4.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3630   -5.6053   -5.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0771   -3.8972   -7.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811   -1.6820   -6.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4475   -3.1140   -4.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6185   -1.5124   -6.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9545    1.4097   -3.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4460   -0.2546   -3.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887   -0.5477   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5848    1.3624   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6781    2.8184   -2.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1513    3.4995   -2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5280    2.6404   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    4.6443    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6896    6.2956    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    6.1302    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.2549    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    2.0164    3.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800    2.6082    4.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308   -2.0439    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8108   -1.8574    3.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4327   -2.8912    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954   -1.3905    2.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -0.1442    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899   -1.6357   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964   -2.7669   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579   -1.4033   -1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.0078   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7628    0.9703   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    0.5417    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8462    1.6488   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6671    1.4513   -2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 13-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z
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     -15.295   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.628   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.961   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -19.501   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.834   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -22.167   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -23.707   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -25.040   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -26.373   1.436   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -27.913   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -29.246   0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -30.579   1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -31.912   0.665   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -31.912  -0.775   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -33.245   1.436   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -34.578   0.665   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -12.090  -0.662   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -13.423  -1.433   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -14.756  -0.662   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -16.296  -0.662   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -17.629  -1.433   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -18.962  -0.662   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -20.502  -0.662   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -21.835  -1.433   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -23.168  -0.662   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -24.708  -0.662   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -26.041  -1.433   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -27.374  -0.662   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -28.914  -0.662   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -30.247  -1.433   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -31.580  -0.662   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -33.120  -0.662   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -34.453  -1.433   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -35.786  -0.662   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   44                                                       
CONECT   22    1   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
CONECT   44   21   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   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                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  130    0
END

COMPND    HMDB0274173
HETATM    1  C1  UNL     1      -4.505  -7.964  -2.682  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.466  -8.554  -3.716  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.701  -9.139  -4.808  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.804  -8.775  -6.048  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.711  -7.710  -6.565  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.833  -6.711  -7.214  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.743  -5.455  -6.880  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.528  -4.839  -5.783  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.318  -3.693  -6.304  1.00  0.00           C  
HETATM   10  C10 UNL     1      -6.140  -2.425  -5.905  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.092  -2.163  -4.893  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.114  -1.191  -5.468  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.862  -0.040  -4.907  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.568   0.377  -3.630  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.604   0.426  -2.540  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.335   1.494  -1.854  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.957   2.790  -2.081  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.705   3.309  -0.908  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.473   4.436  -0.277  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.411   5.347  -0.662  1.00  0.00           C  
HETATM   21  C21 UNL     1      -2.469   5.636   0.534  1.00  0.00           C  
HETATM   22  C22 UNL     1      -1.858   4.362   0.975  1.00  0.00           C  
HETATM   23  O1  UNL     1      -1.735   3.398   0.176  1.00  0.00           O  
HETATM   24  O2  UNL     1      -1.387   4.113   2.275  1.00  0.00           O  
HETATM   25  C23 UNL     1      -0.867   2.846   2.544  1.00  0.00           C  
HETATM   26  C24 UNL     1      -1.717   2.097   3.566  1.00  0.00           C  
HETATM   27  O3  UNL     1      -1.236   0.776   3.714  1.00  0.00           O  
HETATM   28  C25 UNL     1      -1.347  -0.088   2.643  1.00  0.00           C  
HETATM   29  O4  UNL     1      -1.898   0.391   1.580  1.00  0.00           O  
HETATM   30  C26 UNL     1      -0.923  -1.474   2.556  1.00  0.00           C  
HETATM   31  C27 UNL     1       0.355  -1.768   1.861  1.00  0.00           C  
HETATM   32  C28 UNL     1       0.389  -1.236   0.435  1.00  0.00           C  
HETATM   33  C29 UNL     1       1.596  -1.652  -0.281  1.00  0.00           C  
HETATM   34  C30 UNL     1       2.509  -0.899  -0.758  1.00  0.00           C  
HETATM   35  C31 UNL     1       2.584   0.600  -0.700  1.00  0.00           C  
HETATM   36  C32 UNL     1       3.913   0.873  -0.027  1.00  0.00           C  
HETATM   37  C33 UNL     1       4.909   1.496  -0.631  1.00  0.00           C  
HETATM   38  C34 UNL     1       4.815   1.985  -2.011  1.00  0.00           C  
HETATM   39  C35 UNL     1       5.160   3.414  -2.134  1.00  0.00           C  
HETATM   40  C36 UNL     1       4.352   4.343  -2.499  1.00  0.00           C  
HETATM   41  C37 UNL     1       2.956   4.185  -2.845  1.00  0.00           C  
HETATM   42  C38 UNL     1       1.942   4.890  -2.057  1.00  0.00           C  
HETATM   43  C39 UNL     1       2.115   5.648  -1.026  1.00  0.00           C  
HETATM   44  C40 UNL     1       3.313   6.051  -0.310  1.00  0.00           C  
HETATM   45  C41 UNL     1       3.299   5.644   1.152  1.00  0.00           C  
HETATM   46  C42 UNL     1       2.231   6.245   1.988  1.00  0.00           C  
HETATM   47  O5  UNL     1       0.983   5.915   1.566  1.00  0.00           O  
HETATM   48  C43 UNL     1       2.516   5.903   3.448  1.00  0.00           C  
HETATM   49  C44 UNL     1       1.479   6.477   4.357  1.00  0.00           C  
HETATM   50  C45 UNL     1       0.572   2.859   3.059  1.00  0.00           C  
HETATM   51  O6  UNL     1       0.992   1.552   3.314  1.00  0.00           O  
HETATM   52  P1  UNL     1       2.546   1.461   3.907  1.00  0.00           P  
HETATM   53  O7  UNL     1       3.450   2.272   3.011  1.00  0.00           O  
HETATM   54  O8  UNL     1       2.607   2.192   5.454  1.00  0.00           O  
HETATM   55  O9  UNL     1       3.120  -0.110   3.972  1.00  0.00           O  
HETATM   56  C46 UNL     1       4.271  -0.269   4.712  1.00  0.00           C  
HETATM   57  C47 UNL     1       4.746  -1.700   4.747  1.00  0.00           C  
HETATM   58  O10 UNL     1       5.934  -1.706   5.521  1.00  0.00           O  
HETATM   59  C48 UNL     1       3.805  -2.628   5.443  1.00  0.00           C  
HETATM   60  O11 UNL     1       2.569  -2.768   4.854  1.00  0.00           O  
HETATM   61  P2  UNL     1       1.606  -3.851   5.732  1.00  0.00           P  
HETATM   62  O12 UNL     1       2.319  -5.184   5.770  1.00  0.00           O  
HETATM   63  O13 UNL     1       1.467  -3.275   7.301  1.00  0.00           O  
HETATM   64  O14 UNL     1       0.113  -3.988   4.983  1.00  0.00           O  
HETATM   65  H1  UNL     1      -3.521  -7.851  -3.175  1.00  0.00           H  
HETATM   66  H2  UNL     1      -4.410  -8.721  -1.858  1.00  0.00           H  
HETATM   67  H3  UNL     1      -4.876  -7.009  -2.303  1.00  0.00           H  
HETATM   68  H4  UNL     1      -6.032  -9.391  -3.192  1.00  0.00           H  
HETATM   69  H5  UNL     1      -6.169  -7.757  -3.960  1.00  0.00           H  
HETATM   70  H6  UNL     1      -3.989  -9.949  -4.547  1.00  0.00           H  
HETATM   71  H7  UNL     1      -4.186  -9.270  -6.819  1.00  0.00           H  
HETATM   72  H8  UNL     1      -6.435  -7.361  -5.858  1.00  0.00           H  
HETATM   73  H9  UNL     1      -6.355  -8.214  -7.383  1.00  0.00           H  
HETATM   74  H10 UNL     1      -4.185  -7.024  -8.060  1.00  0.00           H  
HETATM   75  H11 UNL     1      -4.028  -4.812  -7.461  1.00  0.00           H  
HETATM   76  H12 UNL     1      -5.020  -4.734  -4.845  1.00  0.00           H  
HETATM   77  H13 UNL     1      -6.363  -5.605  -5.546  1.00  0.00           H  
HETATM   78  H14 UNL     1      -7.077  -3.897  -7.045  1.00  0.00           H  
HETATM   79  H15 UNL     1      -6.781  -1.682  -6.355  1.00  0.00           H  
HETATM   80  H16 UNL     1      -5.474  -1.932  -3.914  1.00  0.00           H  
HETATM   81  H17 UNL     1      -4.448  -3.114  -4.830  1.00  0.00           H  
HETATM   82  H18 UNL     1      -3.619  -1.512  -6.394  1.00  0.00           H  
HETATM   83  H19 UNL     1      -3.132   0.618  -5.380  1.00  0.00           H  
HETATM   84  H20 UNL     1      -4.954   1.410  -3.917  1.00  0.00           H  
HETATM   85  H21 UNL     1      -5.446  -0.255  -3.498  1.00  0.00           H  
HETATM   86  H22 UNL     1      -3.089  -0.548  -2.316  1.00  0.00           H  
HETATM   87  H23 UNL     1      -2.585   1.362  -1.054  1.00  0.00           H  
HETATM   88  H24 UNL     1      -4.678   2.818  -2.930  1.00  0.00           H  
HETATM   89  H25 UNL     1      -3.151   3.499  -2.439  1.00  0.00           H  
HETATM   90  H26 UNL     1      -5.528   2.640  -0.566  1.00  0.00           H  
HETATM   91  H27 UNL     1      -5.155   4.644   0.583  1.00  0.00           H  
HETATM   92  H28 UNL     1      -3.824   6.290  -1.066  1.00  0.00           H  
HETATM   93  H29 UNL     1      -2.753   4.936  -1.423  1.00  0.00           H  
HETATM   94  H30 UNL     1      -1.690   6.296   0.110  1.00  0.00           H  
HETATM   95  H31 UNL     1      -2.982   6.130   1.351  1.00  0.00           H  
HETATM   96  H32 UNL     1      -0.855   2.255   1.629  1.00  0.00           H  
HETATM   97  H33 UNL     1      -2.765   2.016   3.238  1.00  0.00           H  
HETATM   98  H34 UNL     1      -1.580   2.608   4.537  1.00  0.00           H  
HETATM   99  H35 UNL     1      -1.731  -2.044   2.039  1.00  0.00           H  
HETATM  100  H36 UNL     1      -0.811  -1.857   3.612  1.00  0.00           H  
HETATM  101  H37 UNL     1       0.433  -2.891   1.757  1.00  0.00           H  
HETATM  102  H38 UNL     1       1.195  -1.391   2.454  1.00  0.00           H  
HETATM  103  H39 UNL     1       0.316  -0.144   0.479  1.00  0.00           H  
HETATM  104  H40 UNL     1      -0.490  -1.636  -0.139  1.00  0.00           H  
HETATM  105  H41 UNL     1       1.696  -2.767  -0.410  1.00  0.00           H  
HETATM  106  H42 UNL     1       3.358  -1.403  -1.284  1.00  0.00           H  
HETATM  107  H43 UNL     1       2.467   1.008  -1.672  1.00  0.00           H  
HETATM  108  H44 UNL     1       1.763   0.970  -0.057  1.00  0.00           H  
HETATM  109  H45 UNL     1       4.058   0.542   0.993  1.00  0.00           H  
HETATM  110  H46 UNL     1       5.846   1.649  -0.060  1.00  0.00           H  
HETATM  111  H47 UNL     1       5.667   1.451  -2.608  1.00  0.00           H  
HETATM  112  H48 UNL     1       3.908   1.698  -2.529  1.00  0.00           H  
HETATM  113  H49 UNL     1       6.217   3.720  -1.887  1.00  0.00           H  
HETATM  114  H50 UNL     1       4.809   5.364  -2.635  1.00  0.00           H  
HETATM  115  H51 UNL     1       2.644   3.092  -2.919  1.00  0.00           H  
HETATM  116  H52 UNL     1       2.848   4.498  -3.953  1.00  0.00           H  
HETATM  117  H53 UNL     1       0.867   4.740  -2.420  1.00  0.00           H  
HETATM  118  H54 UNL     1       1.169   6.102  -0.613  1.00  0.00           H  
HETATM  119  H55 UNL     1       4.295   5.881  -0.739  1.00  0.00           H  
HETATM  120  H56 UNL     1       3.254   7.212  -0.251  1.00  0.00           H  
HETATM  121  H57 UNL     1       4.284   5.981   1.560  1.00  0.00           H  
HETATM  122  H58 UNL     1       3.272   4.534   1.264  1.00  0.00           H  
HETATM  123  H59 UNL     1       2.298   7.386   1.881  1.00  0.00           H  
HETATM  124  H60 UNL     1       0.319   6.652   1.619  1.00  0.00           H  
HETATM  125  H61 UNL     1       2.606   4.818   3.614  1.00  0.00           H  
HETATM  126  H62 UNL     1       3.497   6.383   3.680  1.00  0.00           H  
HETATM  127  H63 UNL     1       0.814   5.706   4.801  1.00  0.00           H  
HETATM  128  H64 UNL     1       0.861   7.258   3.835  1.00  0.00           H  
HETATM  129  H65 UNL     1       1.973   7.012   5.188  1.00  0.00           H  
HETATM  130  H66 UNL     1       0.649   3.487   3.958  1.00  0.00           H  
HETATM  131  H67 UNL     1       1.207   3.271   2.258  1.00  0.00           H  
HETATM  132  H68 UNL     1       2.452   1.524   6.161  1.00  0.00           H  
HETATM  133  H69 UNL     1       5.091   0.346   4.313  1.00  0.00           H  
HETATM  134  H70 UNL     1       4.145   0.048   5.776  1.00  0.00           H  
HETATM  135  H71 UNL     1       5.045  -2.059   3.742  1.00  0.00           H  
HETATM  136  H72 UNL     1       6.154  -2.683   5.632  1.00  0.00           H  
HETATM  137  H73 UNL     1       3.641  -2.302   6.495  1.00  0.00           H  
HETATM  138  H74 UNL     1       4.255  -3.645   5.479  1.00  0.00           H  
HETATM  139  H75 UNL     1       1.317  -2.311   7.331  1.00  0.00           H  
HETATM  140  H76 UNL     1       0.256  -4.280   4.033  1.00  0.00           H  
CONECT    1    2   65   66   67
CONECT    2    3   68   69
CONECT    3    4    4   70
CONECT    4    5   71
CONECT    5    6   72   73
CONECT    6    7    7   74
CONECT    7    8   75
CONECT    8    9   76   77
CONECT    9   10   10   78
CONECT   10   11   79
CONECT   11   12   80   81
CONECT   12   13   13   82
CONECT   13   14   83
CONECT   14   15   84   85
CONECT   15   16   16   86
CONECT   16   17   87
CONECT   17   18   88   89
CONECT   18   19   19   90
CONECT   19   20   91
CONECT   20   21   92   93
CONECT   21   22   94   95
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   50   96
CONECT   26   27   97   98
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   99  100
CONECT   31   32  101  102
CONECT   32   33  103  104
CONECT   33   34   34  105
CONECT   34   35  106
CONECT   35   36  107  108
CONECT   36   37   37  109
CONECT   37   38  110
CONECT   38   39  111  112
CONECT   39   40   40  113
CONECT   40   41  114
CONECT   41   42  115  116
CONECT   42   43   43  117
CONECT   43   44  118
CONECT   44   45  119  120
CONECT   45   46  121  122
CONECT   46   47   48  123
CONECT   47  124
CONECT   48   49  125  126
CONECT   49  127  128  129
CONECT   50   51  130  131
CONECT   51   52
CONECT   52   53   53   54   55
CONECT   54  132
CONECT   55   56
CONECT   56   57  133  134
CONECT   57   58   59  135
CONECT   58  136
CONECT   59   60  137  138
CONECT   60   61
CONECT   61   62   62   63   64
CONECT   63  139
CONECT   64  140
END

HMDB0274173
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
140139  0  0  0  0  0  0  0  0999 V2000
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   -4.8333   -6.7108   -7.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7171    2.0970    3.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9233   -1.4745    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -1.7682    1.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -1.2362    0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5844    0.5996   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132    0.8727   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1604    3.4139   -2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-{[(5Z,8Z,11Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate	Generator

Chemical Formula

C₄₈H₇₆O₁₄P₂

Average Molecular Weight

939.07

Monoisotopic Molecular Weight

938.471031123

IUPAC Name

[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-{[(5Z,8Z,11Z,14Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-{[(5Z,8Z,11Z,14Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CC[C@@H](O)CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C48H76O14P2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-21-24-27-30-33-36-39-48(52)62-46(43-61-64(56,57)60-41-45(50)40-59-63(53,54)55)42-58-47(51)38-35-32-29-26-23-20-18-17-19-22-25-28-31-34-37-44(49)4-2/h5-6,8-9,11-12,14-15,18-22,24,26,28-31,33,44-46,49-50H,3-4,7,10,13,16-17,23,25,27,32,34-43H2,1-2H3,(H,56,57)(H2,53,54,55)/b6-5-,9-8-,12-11-,15-14-,20-18-,22-19-,24-21-,29-26-,31-28-,33-30-/t44-,45-,46+/m0/s1

InChI Key

AAOBBDXYOCJDLG-WKMKHWRRSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.76	ALOGPS
logP	10.25	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	215.58 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	265.03 m³·mol⁻¹	ChemAxon
Polarizability	100.34 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]+	309.498	32859911
AllCCS	[M+H-H2O]+	309.594	32859911
AllCCS	[M+Na]+	309.337	32859911
AllCCS	[M+NH4]+	309.378	32859911
AllCCS	[M-H]-	317.581	32859911
AllCCS	[M+Na-2H]-	324.702	32859911
AllCCS	[M+HCOO]-	332.459	32859911
DeepCCS	[M+H]+	281.381	30932474
DeepCCS	[M-H]-	278.996	30932474
DeepCCS	[M-2H]-	312.597	30932474
DeepCCS	[M+Na]+	287.294	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF	splash10-000i-3000006097-c7d1b746e70979d93f46	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF	splash10-060c-0100003950-9c586af8924314390552	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF	splash10-0udi-0193000200-bb7af24644c3fd23591d	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF	splash10-000i-0010000009-50751c7d29806c06e89c	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF	splash10-0gb9-4054109013-953fda72250014d6afc1	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF	splash10-0udj-4093123000-f06238365f186107747b	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(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (HMDB0274173)

MOL for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D MOL for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D SDF for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D-SDF for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

PDB for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D PDB for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

SMILES for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

INCHI for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Structure for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D Structure for HMDB0274173 (PGP(20:4(5Z,8Z,11Z,14Z)-OH(18R)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra