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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 16:29:26 UTC

Update Date

2022-11-30 19:57:40 UTC

HMDB ID

HMDB0269561

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))

Description

PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) is an oxidized phosphatidylglycerol (PG). Oxidized phosphatidylglycerols are glycerophospholipids in which a phosphoglycerol moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylglycerols belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)), in particular, consists of one chain of one 11Z-eicosenoyl at the C-1 position and one chain of Lipoxin A5 at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PGs can be synthesized via three different routes. In one route, the oxidized PG is synthetized de novo following the same mechanisms as for PGs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PG backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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

PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
  Mrv1652309122118292D          

 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
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.8990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4771    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1912    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  1  0  0  0  0  0  0  0  0  0
   -6.3660   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0801    0.4166    0.0000 O   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
   -8.6192   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3333   -0.3549    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
  -10.8724   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5865   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3007   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0148   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7289   -0.7679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.7289   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4430   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1571   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9821   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6962   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4104   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 15  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8 12  1  0  0  0  0
  8 11  1  6  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 13  1  1  0  0  0  0
 14 13  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 15 14  1  0  0  0  0
 17 39  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  1  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END

HMDB0269561
     RDKit          3D
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
139138  0  0  0  0  0  0  0  0999 V2000
    7.7289   -7.0941    6.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0671   -7.3650    4.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7339   -6.2135    4.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8843   -6.2921    3.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1730   -7.5093    2.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -7.3135    2.7543 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1054   -8.5718    2.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2596   -6.3090    1.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0226   -5.0346    1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -4.1517    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -2.8629    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412   -2.0417   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7832   -0.7688    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8336   -0.0712    1.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5626    1.2271    1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148    1.9408    0.1349 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0137    1.4432   -0.3511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221    3.4566    0.3212 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1032    3.7902    1.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191    4.1749   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1827    3.8461   -1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2308    4.1398   -1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282    5.5865   -1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745    6.4104   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    6.0529   -1.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    7.3393   -1.2126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2818    7.7113   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983    7.4582    1.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7466    7.7729    2.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8575    8.2811    1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766    7.5329    3.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0940    6.8084    3.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0406    5.4266    3.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806    4.4972    3.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    3.1105    3.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6920    2.4493    3.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327    1.0854    2.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    0.0607    3.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -1.2912    2.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -2.3392    2.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9389   -2.9702    2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -2.6910    0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5558   -3.9144   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543   -3.4950   -1.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3028   -4.4462   -2.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -4.8974   -2.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -5.5808   -1.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721   -6.0729   -2.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9978   -4.8926   -2.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493    7.8065   -2.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    6.9175   -3.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3676    7.3034   -4.5290 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8255    7.6820   -4.3472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753    8.6527   -5.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845    5.9808   -5.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    5.8306   -5.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7313    4.7103   -6.9381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    4.7044   -7.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725    3.3960   -6.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4285    3.3793   -5.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923   -6.7234    6.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4832   -6.3538    6.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8139   -8.0331    6.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1881   -7.5521    4.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6229   -8.3119    4.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2455   -5.2654    4.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -5.3675    2.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4795   -8.4421    3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415   -7.6361    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -7.0680    3.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7102   -8.9635    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -6.6330    0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191   -4.7007    3.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -4.5327   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947   -2.5126    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9773   -2.5039   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149   -0.2112   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.5569    2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844    1.7985    2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    1.7269   -0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576    0.9426    0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0827    3.7230    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    3.6308    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    5.2736   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132    3.8711   -1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090    4.3444   -2.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582    2.7487   -2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6717    3.5492   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337    3.8420   -2.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7710    6.7773    4.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277    7.3633    3.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    5.0076    3.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    5.4759    1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    4.9554    3.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375    4.4067    4.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    3.1418    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460    2.5324    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    3.0929    2.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    2.4481    4.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4851    0.7521    3.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5624    0.3778    3.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479   -1.0727    1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1856   -2.6057    4.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6126   -3.7518    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.5896    0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3848   -4.6837    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6032   -4.2924    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0891   -2.5157   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617   -3.2322   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928   -5.3774   -2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6690   -4.0404   -3.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3204   -3.9682   -3.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -5.5694   -3.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356   -4.7879   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104   -6.3596   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -6.5446   -1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766   -6.8418   -2.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -5.1593   -2.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8783   -4.0258   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218   -4.5463   -3.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5978    8.5037   -5.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5363    3.2675   -5.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7742    2.5548   -6.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
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 56134  1  0
 57135  1  6
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 59137  1  0
 59138  1  0
 60139  1  0
M  END

PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
  Mrv1652309122118292D          

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   -5.6518   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 18  1  0  0  0  0
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  8 12  1  0  0  0  0
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  9 10  1  0  0  0  0
 13  1  1  0  0  0  0
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 29 30  2  0  0  0  0
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 37 38  1  0  0  0  0
 39 40  2  0  0  0  0
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 44 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
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 51 52  1  0  0  0  0
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 53 54  1  0  0  0  0
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 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0269561

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H79O13P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-24-28-34-45(52)56-38-42(39-58-60(54,55)57-37-41(49)36-47)59-46(53)35-29-33-44(51)43(50)32-27-23-21-20-22-26-31-40(48)30-25-6-4-2/h6,12-13,20-23,25-27,31-32,40-44,47-51H,3-5,7-11,14-19,24,28-30,33-39H2,1-2H3,(H,54,55)/b13-12-,22-20+,23-21-,25-6-,31-26+,32-27-/t40-,41-,42+,43+,44+/m0/s1

> <INCHI_KEY>
IOURDWOERWYBSR-ASGMYAANSA-N

> <FORMULA>
C46H79O13P

> <MOLECULAR_WEIGHT>
871.099

> <EXACT_MASS>
870.525829602

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
101.71651553064191

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(11Z)-icos-11-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphinic acid

> <ALOGPS_LOGP>
6.41

> <JCHEM_LOGP>
8.785545158333335

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.34868269947006

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.890911253742865

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6088474575947447

> <JCHEM_POLAR_SURFACE_AREA>
209.51

> <JCHEM_REFRACTIVITY>
243.2090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.41e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy((2R)-3-[(11Z)-icos-11-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0269561
     RDKit          3D
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
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M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.545   2.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.878   1.441   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.138   2.284   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       4.315   3.545   0.000  0.00  0.00           H+0
HETATM   12  O   UNK     0       2.775   3.545   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -32.624   0.665   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -33.957   1.436   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -11.883  -2.873   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -13.216   0.778   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -16.089  -1.433   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -17.422  -0.662   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -18.962  -0.662   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -20.295  -1.433   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -21.628  -0.662   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -22.961  -1.433   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -24.294  -0.662   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -25.627  -1.433   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0     -25.627  -2.873   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0     -26.960  -0.662   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -28.293  -1.433   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -29.833  -1.433   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -31.166  -0.662   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -32.499  -1.433   0.000  0.00  0.00           C+0
CONECT    1   18   13                                                       
CONECT    2   15    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12   11    9                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    1   14                                                       
CONECT   14   13   16   17   15                                             
CONECT   15    2   14                                                       
CONECT   16   14                                                            
CONECT   17   14   39                                                       
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   17   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   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   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  122    0
END

COMPND    HMDB0269561
HETATM    1  C1  UNL     1       7.729  -7.094   6.382  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.067  -7.365   4.909  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.734  -6.213   4.045  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.884  -6.292   3.049  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.173  -7.509   2.679  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.645  -7.313   2.754  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.105  -8.572   2.390  1.00  0.00           O  
HETATM    8  C7  UNL     1       4.260  -6.309   1.744  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.023  -5.035   1.989  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.653  -4.152   0.906  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.405  -2.863   1.102  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.041  -2.042  -0.031  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.783  -0.769   0.082  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.834  -0.071   1.334  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.563   1.227   1.373  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.215   1.941   0.135  1.00  0.00           C  
HETATM   17  O2  UNL     1       1.014   1.443  -0.351  1.00  0.00           O  
HETATM   18  C16 UNL     1       2.122   3.457   0.321  1.00  0.00           C  
HETATM   19  O3  UNL     1       1.103   3.790   1.155  1.00  0.00           O  
HETATM   20  C17 UNL     1       2.219   4.175  -0.978  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.183   3.846  -1.986  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.231   4.140  -1.669  1.00  0.00           C  
HETATM   23  C20 UNL     1      -0.528   5.587  -1.460  1.00  0.00           C  
HETATM   24  O4  UNL     1       0.374   6.410  -1.366  1.00  0.00           O  
HETATM   25  O5  UNL     1      -1.829   6.053  -1.376  1.00  0.00           O  
HETATM   26  C21 UNL     1      -2.270   7.339  -1.213  1.00  0.00           C  
HETATM   27  C22 UNL     1      -3.282   7.711  -0.244  1.00  0.00           C  
HETATM   28  O6  UNL     1      -2.898   7.458   1.094  1.00  0.00           O  
HETATM   29  C23 UNL     1      -3.747   7.773   2.142  1.00  0.00           C  
HETATM   30  O7  UNL     1      -4.857   8.281   1.849  1.00  0.00           O  
HETATM   31  C24 UNL     1      -3.377   7.533   3.522  1.00  0.00           C  
HETATM   32  C25 UNL     1      -2.094   6.808   3.668  1.00  0.00           C  
HETATM   33  C26 UNL     1      -2.041   5.427   3.066  1.00  0.00           C  
HETATM   34  C27 UNL     1      -3.081   4.497   3.643  1.00  0.00           C  
HETATM   35  C28 UNL     1      -3.004   3.110   3.052  1.00  0.00           C  
HETATM   36  C29 UNL     1      -1.692   2.449   3.316  1.00  0.00           C  
HETATM   37  C30 UNL     1      -1.533   1.085   2.748  1.00  0.00           C  
HETATM   38  C31 UNL     1      -2.520   0.061   3.233  1.00  0.00           C  
HETATM   39  C32 UNL     1      -2.226  -1.291   2.558  1.00  0.00           C  
HETATM   40  C33 UNL     1      -3.152  -2.339   2.979  1.00  0.00           C  
HETATM   41  C34 UNL     1      -3.939  -2.970   2.139  1.00  0.00           C  
HETATM   42  C35 UNL     1      -3.972  -2.691   0.715  1.00  0.00           C  
HETATM   43  C36 UNL     1      -3.556  -3.914  -0.139  1.00  0.00           C  
HETATM   44  C37 UNL     1      -3.654  -3.495  -1.557  1.00  0.00           C  
HETATM   45  C38 UNL     1      -3.303  -4.446  -2.618  1.00  0.00           C  
HETATM   46  C39 UNL     1      -1.921  -4.897  -2.837  1.00  0.00           C  
HETATM   47  C40 UNL     1      -1.215  -5.581  -1.727  1.00  0.00           C  
HETATM   48  C41 UNL     1       0.172  -6.073  -2.198  1.00  0.00           C  
HETATM   49  C42 UNL     1       0.998  -4.893  -2.651  1.00  0.00           C  
HETATM   50  C43 UNL     1      -2.749   7.806  -2.634  1.00  0.00           C  
HETATM   51  O8  UNL     1      -3.747   6.918  -3.008  1.00  0.00           O  
HETATM   52  P1  UNL     1      -4.368   7.303  -4.529  1.00  0.00           P  
HETATM   53  O9  UNL     1      -5.826   7.682  -4.347  1.00  0.00           O  
HETATM   54  O10 UNL     1      -3.575   8.653  -5.154  1.00  0.00           O  
HETATM   55  O11 UNL     1      -4.285   5.981  -5.595  1.00  0.00           O  
HETATM   56  C44 UNL     1      -2.972   5.831  -5.979  1.00  0.00           C  
HETATM   57  C45 UNL     1      -2.731   4.710  -6.938  1.00  0.00           C  
HETATM   58  O12 UNL     1      -1.347   4.704  -7.217  1.00  0.00           O  
HETATM   59  C46 UNL     1      -3.073   3.396  -6.280  1.00  0.00           C  
HETATM   60  O13 UNL     1      -4.428   3.379  -5.997  1.00  0.00           O  
HETATM   61  H1  UNL     1       6.692  -6.723   6.481  1.00  0.00           H  
HETATM   62  H2  UNL     1       8.483  -6.354   6.707  1.00  0.00           H  
HETATM   63  H3  UNL     1       7.814  -8.033   6.959  1.00  0.00           H  
HETATM   64  H4  UNL     1       9.188  -7.552   4.890  1.00  0.00           H  
HETATM   65  H5  UNL     1       7.623  -8.312   4.635  1.00  0.00           H  
HETATM   66  H6  UNL     1       8.246  -5.265   4.286  1.00  0.00           H  
HETATM   67  H7  UNL     1       6.704  -5.367   2.458  1.00  0.00           H  
HETATM   68  H8  UNL     1       6.479  -8.442   3.115  1.00  0.00           H  
HETATM   69  H9  UNL     1       6.341  -7.636   1.554  1.00  0.00           H  
HETATM   70  H10 UNL     1       4.292  -7.068   3.748  1.00  0.00           H  
HETATM   71  H11 UNL     1       4.710  -8.964   1.741  1.00  0.00           H  
HETATM   72  H12 UNL     1       4.159  -6.633   0.708  1.00  0.00           H  
HETATM   73  H13 UNL     1       4.119  -4.701   3.015  1.00  0.00           H  
HETATM   74  H14 UNL     1       3.568  -4.533  -0.096  1.00  0.00           H  
HETATM   75  H15 UNL     1       3.495  -2.513   2.113  1.00  0.00           H  
HETATM   76  H16 UNL     1       2.977  -2.504  -1.039  1.00  0.00           H  
HETATM   77  H17 UNL     1       2.515  -0.211  -0.823  1.00  0.00           H  
HETATM   78  H18 UNL     1       3.088  -0.557   2.266  1.00  0.00           H  
HETATM   79  H19 UNL     1       2.584   1.799   2.294  1.00  0.00           H  
HETATM   80  H20 UNL     1       2.964   1.727  -0.683  1.00  0.00           H  
HETATM   81  H21 UNL     1       0.558   0.943   0.367  1.00  0.00           H  
HETATM   82  H22 UNL     1       3.083   3.723   0.886  1.00  0.00           H  
HETATM   83  H23 UNL     1       1.304   3.631   2.115  1.00  0.00           H  
HETATM   84  H24 UNL     1       2.334   5.274  -0.817  1.00  0.00           H  
HETATM   85  H25 UNL     1       3.213   3.871  -1.430  1.00  0.00           H  
HETATM   86  H26 UNL     1       1.409   4.344  -2.967  1.00  0.00           H  
HETATM   87  H27 UNL     1       1.258   2.749  -2.208  1.00  0.00           H  
HETATM   88  H28 UNL     1      -0.672   3.549  -0.842  1.00  0.00           H  
HETATM   89  H29 UNL     1      -0.834   3.842  -2.575  1.00  0.00           H  
HETATM   90  H30 UNL     1      -1.351   7.994  -1.085  1.00  0.00           H  
HETATM   91  H31 UNL     1      -4.318   7.362  -0.453  1.00  0.00           H  
HETATM   92  H32 UNL     1      -3.392   8.840  -0.282  1.00  0.00           H  
HETATM   93  H33 UNL     1      -3.406   8.468   4.151  1.00  0.00           H  
HETATM   94  H34 UNL     1      -4.173   6.861   3.967  1.00  0.00           H  
HETATM   95  H35 UNL     1      -1.771   6.777   4.756  1.00  0.00           H  
HETATM   96  H36 UNL     1      -1.228   7.363   3.188  1.00  0.00           H  
HETATM   97  H37 UNL     1      -0.997   5.008   3.203  1.00  0.00           H  
HETATM   98  H38 UNL     1      -2.198   5.476   1.981  1.00  0.00           H  
HETATM   99  H39 UNL     1      -4.084   4.955   3.384  1.00  0.00           H  
HETATM  100  H40 UNL     1      -2.937   4.407   4.724  1.00  0.00           H  
HETATM  101  H41 UNL     1      -3.144   3.142   1.944  1.00  0.00           H  
HETATM  102  H42 UNL     1      -3.846   2.532   3.534  1.00  0.00           H  
HETATM  103  H43 UNL     1      -0.890   3.093   2.883  1.00  0.00           H  
HETATM  104  H44 UNL     1      -1.455   2.448   4.425  1.00  0.00           H  
HETATM  105  H45 UNL     1      -1.547   1.087   1.629  1.00  0.00           H  
HETATM  106  H46 UNL     1      -0.485   0.752   3.006  1.00  0.00           H  
HETATM  107  H47 UNL     1      -2.423  -0.087   4.332  1.00  0.00           H  
HETATM  108  H48 UNL     1      -3.562   0.378   3.043  1.00  0.00           H  
HETATM  109  H49 UNL     1      -2.148  -1.073   1.500  1.00  0.00           H  
HETATM  110  H50 UNL     1      -1.198  -1.553   2.992  1.00  0.00           H  
HETATM  111  H51 UNL     1      -3.186  -2.606   4.056  1.00  0.00           H  
HETATM  112  H52 UNL     1      -4.613  -3.752   2.512  1.00  0.00           H  
HETATM  113  H53 UNL     1      -5.082  -2.590   0.447  1.00  0.00           H  
HETATM  114  H54 UNL     1      -3.509  -1.788   0.349  1.00  0.00           H  
HETATM  115  H55 UNL     1      -4.385  -4.684   0.017  1.00  0.00           H  
HETATM  116  H56 UNL     1      -2.603  -4.292   0.208  1.00  0.00           H  
HETATM  117  H57 UNL     1      -3.089  -2.516  -1.736  1.00  0.00           H  
HETATM  118  H58 UNL     1      -4.762  -3.232  -1.724  1.00  0.00           H  
HETATM  119  H59 UNL     1      -3.993  -5.377  -2.542  1.00  0.00           H  
HETATM  120  H60 UNL     1      -3.669  -4.040  -3.641  1.00  0.00           H  
HETATM  121  H61 UNL     1      -1.320  -3.968  -3.171  1.00  0.00           H  
HETATM  122  H62 UNL     1      -1.839  -5.569  -3.748  1.00  0.00           H  
HETATM  123  H63 UNL     1      -0.936  -4.788  -0.957  1.00  0.00           H  
HETATM  124  H64 UNL     1      -1.810  -6.360  -1.267  1.00  0.00           H  
HETATM  125  H65 UNL     1       0.634  -6.545  -1.309  1.00  0.00           H  
HETATM  126  H66 UNL     1       0.077  -6.842  -2.976  1.00  0.00           H  
HETATM  127  H67 UNL     1       2.061  -5.159  -2.690  1.00  0.00           H  
HETATM  128  H68 UNL     1       0.878  -4.026  -1.970  1.00  0.00           H  
HETATM  129  H69 UNL     1       0.622  -4.546  -3.652  1.00  0.00           H  
HETATM  130  H70 UNL     1      -3.203   8.813  -2.542  1.00  0.00           H  
HETATM  131  H71 UNL     1      -1.906   7.806  -3.332  1.00  0.00           H  
HETATM  132  H72 UNL     1      -2.598   8.504  -5.148  1.00  0.00           H  
HETATM  133  H73 UNL     1      -2.604   6.785  -6.430  1.00  0.00           H  
HETATM  134  H74 UNL     1      -2.370   5.606  -5.063  1.00  0.00           H  
HETATM  135  H75 UNL     1      -3.245   4.829  -7.911  1.00  0.00           H  
HETATM  136  H76 UNL     1      -0.912   4.095  -6.559  1.00  0.00           H  
HETATM  137  H77 UNL     1      -2.536   3.268  -5.318  1.00  0.00           H  
HETATM  138  H78 UNL     1      -2.774   2.555  -6.951  1.00  0.00           H  
HETATM  139  H79 UNL     1      -4.581   2.639  -5.345  1.00  0.00           H  
CONECT    1    2   61   62   63
CONECT    2    3   64   65
CONECT    3    4    4   66
CONECT    4    5   67
CONECT    5    6   68   69
CONECT    6    7    8   70
CONECT    7   71
CONECT    8    9    9   72
CONECT    9   10   73
CONECT   10   11   11   74
CONECT   11   12   75
CONECT   12   13   13   76
CONECT   13   14   77
CONECT   14   15   15   78
CONECT   15   16   79
CONECT   16   17   18   80
CONECT   17   81
CONECT   18   19   20   82
CONECT   19   83
CONECT   20   21   84   85
CONECT   21   22   86   87
CONECT   22   23   88   89
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   27   50   90
CONECT   27   28   91   92
CONECT   28   29
CONECT   29   30   30   31
CONECT   31   32   93   94
CONECT   32   33   95   96
CONECT   33   34   97   98
CONECT   34   35   99  100
CONECT   35   36  101  102
CONECT   36   37  103  104
CONECT   37   38  105  106
CONECT   38   39  107  108
CONECT   39   40  109  110
CONECT   40   41   41  111
CONECT   41   42  112
CONECT   42   43  113  114
CONECT   43   44  115  116
CONECT   44   45  117  118
CONECT   45   46  119  120
CONECT   46   47  121  122
CONECT   47   48  123  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  139
END

HMDB0269561
     RDKit          3D
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
139138  0  0  0  0  0  0  0  0999 V2000
    7.7289   -7.0941    6.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1730   -7.5093    2.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -7.3135    2.7543 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6525   -4.1517    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -2.8629    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2148    1.9408    0.1349 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0137    1.4432   -0.3511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221    3.4566    0.3212 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2S)-2,3-Dihydroxypropoxy][(2R)-3-[(11Z)-icos-11-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphinate	Generator

Chemical Formula

C₄₆H₇₉O₁₃P

Average Molecular Weight

871.099

Monoisotopic Molecular Weight

870.525829602

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(11Z)-icos-11-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-3-[(11Z)-icos-11-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H79O13P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-24-28-34-45(52)56-38-42(39-58-60(54,55)57-37-41(49)36-47)59-46(53)35-29-33-44(51)43(50)32-27-23-21-20-22-26-31-40(48)30-25-6-4-2/h6,12-13,20-23,25-27,31-32,40-44,47-51H,3-5,7-11,14-19,24,28-30,33-39H2,1-2H3,(H,54,55)/b13-12-,22-20+,23-21-,25-6-,31-26+,32-27-/t40-,41-,42+,43+,44+/m0/s1

InChI Key

IOURDWOERWYBSR-ASGMYAANSA-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	6.41	ALOGPS
logP	8.79	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	243.21 m³·mol⁻¹	ChemAxon
Polarizability	101.72 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]+	299.504	32859911
AllCCS	[M+H-H2O]+	299.635	32859911
AllCCS	[M+Na]+	299.297	32859911
AllCCS	[M+NH4]+	299.348	32859911
AllCCS	[M-H]-	299.736	32859911
AllCCS	[M+Na-2H]-	306.839	32859911
AllCCS	[M+HCOO]-	314.609	32859911
DeepCCS	[M+H]+	284.117	30932474
DeepCCS	[M-H]-	281.721	30932474
DeepCCS	[M-2H]-	314.655	30932474
DeepCCS	[M+Na]+	291.019	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC	6290.6	Standard polar	33892256
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC	4790.1	Standard non polar	33892256
PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC	6456.2	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 10V, Negative-QTOF	splash10-014i-0000000090-86b823bdf0cee6204ae1	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 20V, Negative-QTOF	splash10-0b92-0009130040-cf4d17082f25ba423955	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 40V, Negative-QTOF	splash10-0b92-0109130040-d9800493234e5e723708	2021-09-28	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) (HMDB0269561)

MOL for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

3D MOL for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

3D SDF for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

3D-SDF for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

PDB for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

3D PDB for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

SMILES for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

INCHI for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

Structure for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

3D Structure for HMDB0269561 (PG(20:1(11Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra