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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-13 17:41:35 UTC

Update Date

2022-11-30 20:03:20 UTC

HMDB ID

HMDB0281830

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PS(18:3(6Z,9Z,12Z)/PGF1alpha)

Description

PS(18:3(6Z,9Z,12Z)/PGF1alpha) is an oxidized phosphatidylserine (PS). Oxidized phosphatidylserines are glycerophospholipids in which a phosphorylserine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylserines 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, phosphatidylserines 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. PS(18:3(6Z,9Z,12Z)/PGF1alpha), in particular, consists of one chain of one 6Z,9Z,12Z-octadecatrienoyl at the C-1 position and one chain of Prostaglandin F1alpha 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 PSs can be synthesized via three different routes. In one route, the oxidized PS is synthetized de novo following the same mechanisms as for PSs 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 PS backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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


  Mrv1652309132119412D          

 59 59  0  0  1  0            999 V2000
    1.1033  -15.3611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178  -14.9486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8178  -14.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -13.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -12.8861    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073  -12.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573  -12.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -12.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -11.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -10.8236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5323  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178  -10.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -9.5861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -9.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980   -9.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980   -8.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -7.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -8.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546   -7.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546   -7.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401   -6.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401   -5.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -5.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -4.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612  -10.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757  -11.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3901  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5336  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2480  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9625  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6770  -10.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7632   -9.5906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1501   -9.0386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5702   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9827  -10.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8032  -10.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4306  -10.7466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6022  -11.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3868  -11.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5583  -12.6155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9452  -13.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3429  -12.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5145  -13.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2991  -13.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4706  -14.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2552  -14.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -15.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -14.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -16.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 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
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 40  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  6  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
  2 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
M  END

HMDB0281830
     RDKit          3D
PS(18:3(6Z,9Z,12Z)/PGF1alpha)
135135  0  0  0  0  0  0  0  0999 V2000
  -16.5220    2.6132   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2441    3.7137   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1586    3.1836    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9710    2.8738   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8398    2.3157    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4851    3.3221    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3313    3.9008    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0986    3.7579    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0053    2.9060   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2408    1.8584   -0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3584    1.4296    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7903    0.0532    0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9786   -0.9679    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5667   -0.8665    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2389   -1.6917   -0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645   -1.5397   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.1418   -1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456   -0.2067   -1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -0.5313   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    0.1142   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546    0.1191   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -1.2563   -0.8471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.2564    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2302   -3.5416   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -4.6569    0.8228 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.4017   -4.2911    1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -4.8513    2.2354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349   -6.1257   -0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236   -6.4201   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -7.7089   -1.0998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2147   -7.6445   -2.3647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343   -8.8703   -0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874   -9.1553    0.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -9.6880   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077   -1.1431   -0.7346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.2416   -1.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8008   -1.4545   -2.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140   -1.1051   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479   -0.7513   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.5716    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    0.8836    1.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9903    0.9439    2.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128    1.9673    1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2168    2.0915    2.0290 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4223    2.4322    3.4761 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3962    3.1411    4.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7498    1.1438    4.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3359    0.2232    3.1212 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6991   -1.0500    3.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0830    0.8593    1.8048 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2600    1.1850    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5109    1.0660    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6686    1.4257    0.4081 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3059    0.2406    0.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2203    2.1771   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3588    2.5805   -1.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1938    1.4787   -2.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    2.0654   -3.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1257    0.9557   -3.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3844    1.6066   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5576    2.6623   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7843    2.6823   -2.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1203    4.0404   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7443    4.5729   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5385    2.2901    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9530    3.9427    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1745    2.1366   -1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5367    3.8229   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3936    1.4587    0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0989    1.8956   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2779    3.6312    2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2830    4.6594    2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8129    4.8249    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2741    3.6715    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6114    3.1825   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2160    1.2433   -1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3068    1.3953    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2950    2.0891    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8484   -0.1221    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3559   -1.9956    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0201   -1.4670    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848    0.0932    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4062   -2.7525   -0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8582   -1.4751   -1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5391   -2.1580   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1702   -1.9095   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.2580   -2.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903    0.5910   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911    0.3791    0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    0.8266   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -1.4624   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -2.2749   -0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -1.9616    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315   -4.2650    2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -5.6144   -0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -6.5595    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355   -7.8734   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952   -7.9693   -2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1321   -6.7163   -2.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283  -10.5077   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850   -2.0566   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582   -0.2659   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -1.5565    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0451   -0.7729    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928    0.6910    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987    1.3383   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767    1.7742    2.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951    0.0237    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3738   -0.0934    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478    1.1382    3.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2947    2.9488    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8065    1.7373    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778    2.9035    1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3319    3.0683    3.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0218    2.7474    4.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5314    1.2759    4.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904    0.6872    4.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3923   -0.0163    3.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529   -1.3079    4.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421    0.1771    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0532    1.5810   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8035    0.6971    2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3639    2.0263    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5405   -0.3254    0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5534    1.4787   -1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5695    3.0506   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0234    3.2988   -2.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0837    3.2279   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7742    0.9609   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5993    0.7599   -2.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8142    2.7143   -3.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9139    2.7608   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9783    0.0479   -3.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7908    0.7035   -4.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1976    1.2685   -3.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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 59133  1  0
 59134  1  0
 59135  1  0
M  END


  Mrv1652309132119412D          

 59 59  0  0  1  0            999 V2000
    1.1033  -15.3611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178  -14.9486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8178  -14.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -13.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -12.8861    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073  -12.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573  -12.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -12.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -11.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -10.8236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5323  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178  -10.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -9.5861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1835   -9.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980   -9.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980   -8.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -7.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -8.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546   -7.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546   -7.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401   -6.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401   -5.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -5.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -4.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612  -10.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757  -11.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3901  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5336  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2480  -10.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9625  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6770  -10.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7632   -9.5906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1501   -9.0386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5702   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9827  -10.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8032  -10.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4306  -10.7466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6022  -11.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3868  -11.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5583  -12.6155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9452  -13.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3429  -12.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5145  -13.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2991  -13.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4706  -14.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2552  -14.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -15.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -14.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323  -16.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 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
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 40  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  6  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
  2 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0281830

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C44H76NO13P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-23-27-42(49)55-32-36(33-56-59(53,54)57-34-39(45)44(51)52)58-43(50)28-24-20-19-22-26-37-38(41(48)31-40(37)47)30-29-35(46)25-21-6-4-2/h9-10,12-13,15-16,29-30,35-41,46-48H,3-8,11,14,17-28,31-34,45H2,1-2H3,(H,51,52)(H,53,54)/b10-9-,13-12-,16-15-,30-29+/t35-,36+,37+,38+,39-,40-,41+/m0/s1

> <INCHI_KEY>
BFVBJWAWLZXBIQ-HKYIHLRTSA-N

> <FORMULA>
C44H76NO13P

> <MOLECULAR_WEIGHT>
858.06

> <EXACT_MASS>
857.505428509

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
135

> <JCHEM_AVERAGE_POLARIZABILITY>
95.34823052638393

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
6.01317173902188

> <ALOGPS_LOGS>
-6.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.178464098503445

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4683152650354563

> <JCHEM_PKA_STRONGEST_BASIC>
9.376601339487568

> <JCHEM_POLAR_SURFACE_AREA>
232.36999999999998

> <JCHEM_REFRACTIVITY>
231.6561000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.07e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0281830
     RDKit          3D
PS(18:3(6Z,9Z,12Z)/PGF1alpha)
135135  0  0  0  0  0  0  0  0999 V2000
  -16.5220    2.6132   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2441    3.7137   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1586    3.1836    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9710    2.8738   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8398    2.3157    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4851    3.3221    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3313    3.9008    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0986    3.7579    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0053    2.9060   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2408    1.8584   -0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3584    1.4296    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7903    0.0532    0.8845 C   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    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-21         0                                  
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HETATM   40  C   UNK     0      16.730 -20.204   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      18.064 -19.434   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.225 -17.902   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      17.080 -16.872   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      19.731 -17.582   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.501 -18.916   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      22.033 -19.077   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      19.471 -20.060   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      19.791 -21.567   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      21.255 -22.043   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      21.576 -23.549   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      20.431 -24.579   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      23.040 -24.025   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.360 -25.531   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      24.825 -26.007   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      25.145 -27.513   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      26.610 -27.989   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.727 -28.674   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       6.061 -27.904   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       4.727 -30.214   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   57                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   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                                                            
CONECT   32   10   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   47                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   41   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57    2   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

COMPND    HMDB0281830
HETATM    1  C1  UNL     1     -16.522   2.613  -1.642  1.00  0.00           C  
HETATM    2  C2  UNL     1     -16.244   3.714  -0.653  1.00  0.00           C  
HETATM    3  C3  UNL     1     -15.159   3.184   0.301  1.00  0.00           C  
HETATM    4  C4  UNL     1     -13.971   2.874  -0.554  1.00  0.00           C  
HETATM    5  C5  UNL     1     -12.840   2.316   0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1     -12.485   3.322   1.318  1.00  0.00           C  
HETATM    7  C7  UNL     1     -11.331   3.901   1.438  1.00  0.00           C  
HETATM    8  C8  UNL     1     -10.099   3.758   0.678  1.00  0.00           C  
HETATM    9  C9  UNL     1     -10.005   2.906  -0.473  1.00  0.00           C  
HETATM   10  C10 UNL     1      -9.241   1.858  -0.578  1.00  0.00           C  
HETATM   11  C11 UNL     1      -8.358   1.430   0.535  1.00  0.00           C  
HETATM   12  C12 UNL     1      -8.790   0.053   0.884  1.00  0.00           C  
HETATM   13  C13 UNL     1      -7.979  -0.968   0.850  1.00  0.00           C  
HETATM   14  C14 UNL     1      -6.567  -0.867   0.471  1.00  0.00           C  
HETATM   15  C15 UNL     1      -6.239  -1.692  -0.761  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.765  -1.540  -1.070  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.338  -0.142  -1.367  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.846  -0.207  -1.603  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.338  -0.531  -2.682  1.00  0.00           O  
HETATM   20  O2  UNL     1      -2.030   0.114  -0.552  1.00  0.00           O  
HETATM   21  C19 UNL     1      -0.655   0.119  -0.536  1.00  0.00           C  
HETATM   22  C20 UNL     1      -0.042  -1.256  -0.847  1.00  0.00           C  
HETATM   23  C21 UNL     1      -0.715  -2.256   0.047  1.00  0.00           C  
HETATM   24  O3  UNL     1      -0.230  -3.542  -0.185  1.00  0.00           O  
HETATM   25  P1  UNL     1      -0.988  -4.657   0.823  1.00  0.00           P  
HETATM   26  O4  UNL     1      -2.402  -4.291   1.158  1.00  0.00           O  
HETATM   27  O5  UNL     1      -0.076  -4.851   2.235  1.00  0.00           O  
HETATM   28  O6  UNL     1      -1.035  -6.126  -0.060  1.00  0.00           O  
HETATM   29  C22 UNL     1       0.324  -6.420  -0.313  1.00  0.00           C  
HETATM   30  C23 UNL     1       0.453  -7.709  -1.100  1.00  0.00           C  
HETATM   31  N1  UNL     1      -0.215  -7.644  -2.365  1.00  0.00           N  
HETATM   32  C24 UNL     1      -0.034  -8.870  -0.324  1.00  0.00           C  
HETATM   33  O7  UNL     1       0.387  -9.155   0.808  1.00  0.00           O  
HETATM   34  O8  UNL     1      -1.019  -9.688  -0.892  1.00  0.00           O  
HETATM   35  O9  UNL     1       1.308  -1.143  -0.735  1.00  0.00           O  
HETATM   36  C25 UNL     1       2.231  -1.242  -1.733  1.00  0.00           C  
HETATM   37  O10 UNL     1       1.801  -1.454  -2.892  1.00  0.00           O  
HETATM   38  C26 UNL     1       3.714  -1.105  -1.467  1.00  0.00           C  
HETATM   39  C27 UNL     1       3.948  -0.751  -0.019  1.00  0.00           C  
HETATM   40  C28 UNL     1       3.359   0.572   0.379  1.00  0.00           C  
HETATM   41  C29 UNL     1       3.556   0.884   1.829  1.00  0.00           C  
HETATM   42  C30 UNL     1       4.990   0.944   2.283  1.00  0.00           C  
HETATM   43  C31 UNL     1       5.813   1.967   1.606  1.00  0.00           C  
HETATM   44  C32 UNL     1       7.217   2.091   2.029  1.00  0.00           C  
HETATM   45  C33 UNL     1       7.422   2.432   3.476  1.00  0.00           C  
HETATM   46  O11 UNL     1       6.396   3.141   4.043  1.00  0.00           O  
HETATM   47  C34 UNL     1       7.750   1.144   4.183  1.00  0.00           C  
HETATM   48  C35 UNL     1       8.336   0.223   3.121  1.00  0.00           C  
HETATM   49  O12 UNL     1       7.699  -1.050   3.199  1.00  0.00           O  
HETATM   50  C36 UNL     1       8.083   0.859   1.805  1.00  0.00           C  
HETATM   51  C37 UNL     1       9.260   1.185   0.988  1.00  0.00           C  
HETATM   52  C38 UNL     1      10.511   1.066   1.311  1.00  0.00           C  
HETATM   53  C39 UNL     1      11.669   1.426   0.408  1.00  0.00           C  
HETATM   54  O13 UNL     1      12.306   0.241   0.015  1.00  0.00           O  
HETATM   55  C40 UNL     1      11.220   2.177  -0.785  1.00  0.00           C  
HETATM   56  C41 UNL     1      12.359   2.580  -1.663  1.00  0.00           C  
HETATM   57  C42 UNL     1      13.194   1.479  -2.234  1.00  0.00           C  
HETATM   58  C43 UNL     1      14.289   2.065  -3.149  1.00  0.00           C  
HETATM   59  C44 UNL     1      15.126   0.956  -3.720  1.00  0.00           C  
HETATM   60  H1  UNL     1     -16.384   1.607  -1.208  1.00  0.00           H  
HETATM   61  H2  UNL     1     -17.558   2.662  -2.014  1.00  0.00           H  
HETATM   62  H3  UNL     1     -15.784   2.682  -2.495  1.00  0.00           H  
HETATM   63  H4  UNL     1     -17.120   4.040  -0.088  1.00  0.00           H  
HETATM   64  H5  UNL     1     -15.744   4.573  -1.185  1.00  0.00           H  
HETATM   65  H6  UNL     1     -15.538   2.290   0.822  1.00  0.00           H  
HETATM   66  H7  UNL     1     -14.953   3.943   1.068  1.00  0.00           H  
HETATM   67  H8  UNL     1     -14.175   2.137  -1.329  1.00  0.00           H  
HETATM   68  H9  UNL     1     -13.537   3.823  -0.978  1.00  0.00           H  
HETATM   69  H10 UNL     1     -13.394   1.459   0.877  1.00  0.00           H  
HETATM   70  H11 UNL     1     -12.099   1.896  -0.316  1.00  0.00           H  
HETATM   71  H12 UNL     1     -13.278   3.631   2.072  1.00  0.00           H  
HETATM   72  H13 UNL     1     -11.283   4.659   2.302  1.00  0.00           H  
HETATM   73  H14 UNL     1      -9.813   4.825   0.249  1.00  0.00           H  
HETATM   74  H15 UNL     1      -9.274   3.672   1.440  1.00  0.00           H  
HETATM   75  H16 UNL     1     -10.611   3.183  -1.365  1.00  0.00           H  
HETATM   76  H17 UNL     1      -9.216   1.243  -1.502  1.00  0.00           H  
HETATM   77  H18 UNL     1      -7.307   1.395   0.122  1.00  0.00           H  
HETATM   78  H19 UNL     1      -8.295   2.089   1.389  1.00  0.00           H  
HETATM   79  H20 UNL     1      -9.848  -0.122   1.189  1.00  0.00           H  
HETATM   80  H21 UNL     1      -8.356  -1.996   1.121  1.00  0.00           H  
HETATM   81  H22 UNL     1      -6.020  -1.467   1.308  1.00  0.00           H  
HETATM   82  H23 UNL     1      -6.085   0.093   0.530  1.00  0.00           H  
HETATM   83  H24 UNL     1      -6.406  -2.752  -0.495  1.00  0.00           H  
HETATM   84  H25 UNL     1      -6.858  -1.475  -1.629  1.00  0.00           H  
HETATM   85  H26 UNL     1      -4.539  -2.158  -1.964  1.00  0.00           H  
HETATM   86  H27 UNL     1      -4.170  -1.910  -0.207  1.00  0.00           H  
HETATM   87  H28 UNL     1      -4.804   0.258  -2.295  1.00  0.00           H  
HETATM   88  H29 UNL     1      -4.490   0.591  -0.559  1.00  0.00           H  
HETATM   89  H30 UNL     1      -0.291   0.379   0.488  1.00  0.00           H  
HETATM   90  H31 UNL     1      -0.187   0.827  -1.256  1.00  0.00           H  
HETATM   91  H32 UNL     1      -0.362  -1.462  -1.889  1.00  0.00           H  
HETATM   92  H33 UNL     1      -1.789  -2.275  -0.235  1.00  0.00           H  
HETATM   93  H34 UNL     1      -0.690  -1.962   1.116  1.00  0.00           H  
HETATM   94  H35 UNL     1      -0.431  -4.265   2.962  1.00  0.00           H  
HETATM   95  H36 UNL     1       0.841  -5.614  -0.839  1.00  0.00           H  
HETATM   96  H37 UNL     1       0.780  -6.559   0.684  1.00  0.00           H  
HETATM   97  H38 UNL     1       1.536  -7.873  -1.282  1.00  0.00           H  
HETATM   98  H39 UNL     1      -1.195  -7.969  -2.281  1.00  0.00           H  
HETATM   99  H40 UNL     1      -0.132  -6.716  -2.841  1.00  0.00           H  
HETATM  100  H41 UNL     1      -0.728 -10.508  -1.419  1.00  0.00           H  
HETATM  101  H42 UNL     1       4.185  -2.057  -1.712  1.00  0.00           H  
HETATM  102  H43 UNL     1       4.058  -0.266  -2.087  1.00  0.00           H  
HETATM  103  H44 UNL     1       3.552  -1.556   0.663  1.00  0.00           H  
HETATM  104  H45 UNL     1       5.045  -0.773   0.137  1.00  0.00           H  
HETATM  105  H46 UNL     1       2.293   0.691   0.160  1.00  0.00           H  
HETATM  106  H47 UNL     1       3.899   1.338  -0.260  1.00  0.00           H  
HETATM  107  H48 UNL     1       2.977   1.774   2.158  1.00  0.00           H  
HETATM  108  H49 UNL     1       3.095   0.024   2.403  1.00  0.00           H  
HETATM  109  H50 UNL     1       5.374  -0.093   2.185  1.00  0.00           H  
HETATM  110  H51 UNL     1       4.948   1.138   3.385  1.00  0.00           H  
HETATM  111  H52 UNL     1       5.295   2.949   1.680  1.00  0.00           H  
HETATM  112  H53 UNL     1       5.806   1.737   0.501  1.00  0.00           H  
HETATM  113  H54 UNL     1       7.678   2.904   1.394  1.00  0.00           H  
HETATM  114  H55 UNL     1       8.332   3.068   3.542  1.00  0.00           H  
HETATM  115  H56 UNL     1       6.022   2.747   4.852  1.00  0.00           H  
HETATM  116  H57 UNL     1       8.531   1.276   4.957  1.00  0.00           H  
HETATM  117  H58 UNL     1       6.890   0.687   4.707  1.00  0.00           H  
HETATM  118  H59 UNL     1       9.392  -0.016   3.340  1.00  0.00           H  
HETATM  119  H60 UNL     1       7.553  -1.308   4.146  1.00  0.00           H  
HETATM  120  H61 UNL     1       7.442   0.177   1.159  1.00  0.00           H  
HETATM  121  H62 UNL     1       9.053   1.581  -0.023  1.00  0.00           H  
HETATM  122  H63 UNL     1      10.804   0.697   2.269  1.00  0.00           H  
HETATM  123  H64 UNL     1      12.364   2.026   1.016  1.00  0.00           H  
HETATM  124  H65 UNL     1      12.541  -0.325   0.792  1.00  0.00           H  
HETATM  125  H66 UNL     1      10.553   1.479  -1.392  1.00  0.00           H  
HETATM  126  H67 UNL     1      10.569   3.051  -0.542  1.00  0.00           H  
HETATM  127  H68 UNL     1      12.023   3.299  -2.470  1.00  0.00           H  
HETATM  128  H69 UNL     1      13.084   3.228  -1.069  1.00  0.00           H  
HETATM  129  H70 UNL     1      13.774   0.961  -1.423  1.00  0.00           H  
HETATM  130  H71 UNL     1      12.599   0.760  -2.814  1.00  0.00           H  
HETATM  131  H72 UNL     1      13.814   2.714  -3.914  1.00  0.00           H  
HETATM  132  H73 UNL     1      14.914   2.761  -2.515  1.00  0.00           H  
HETATM  133  H74 UNL     1      14.978   0.048  -3.088  1.00  0.00           H  
HETATM  134  H75 UNL     1      14.791   0.703  -4.761  1.00  0.00           H  
HETATM  135  H76 UNL     1      16.198   1.268  -3.695  1.00  0.00           H  
CONECT    1    2   60   61   62
CONECT    2    3   63   64
CONECT    3    4   65   66
CONECT    4    5   67   68
CONECT    5    6   69   70
CONECT    6    7    7   71
CONECT    7    8   72
CONECT    8    9   73   74
CONECT    9   10   10   75
CONECT   10   11   76
CONECT   11   12   77   78
CONECT   12   13   13   79
CONECT   13   14   80
CONECT   14   15   81   82
CONECT   15   16   83   84
CONECT   16   17   85   86
CONECT   17   18   87   88
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   89   90
CONECT   22   23   35   91
CONECT   23   24   92   93
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   94
CONECT   28   29
CONECT   29   30   95   96
CONECT   30   31   32   97
CONECT   31   98   99
CONECT   32   33   33   34
CONECT   34  100
CONECT   35   36
CONECT   36   37   37   38
CONECT   38   39  101  102
CONECT   39   40  103  104
CONECT   40   41  105  106
CONECT   41   42  107  108
CONECT   42   43  109  110
CONECT   43   44  111  112
CONECT   44   45   50  113
CONECT   45   46   47  114
CONECT   46  115
CONECT   47   48  116  117
CONECT   48   49   50  118
CONECT   49  119
CONECT   50   51  120
CONECT   51   52   52  121
CONECT   52   53  122
CONECT   53   54   55  123
CONECT   54  124
CONECT   55   56  125  126
CONECT   56   57  127  128
CONECT   57   58  129  130
CONECT   58   59  131  132
CONECT   59  133  134  135
END

HMDB0281830
     RDKit          3D
PS(18:3(6Z,9Z,12Z)/PGF1alpha)
135135  0  0  0  0  0  0  0  0999 V2000
  -16.5220    2.6132   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2441    3.7137   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1586    3.1836    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9710    2.8738   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8398    2.3157    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4851    3.3221    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3313    3.9008    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0986    3.7579    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0053    2.9060   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2408    1.8584   -0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3584    1.4296    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7903    0.0532    0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-({[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-[(6Z,9Z)-octadeca-6,9,12-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoate	HMDB

Chemical Formula

C₄₄H₇₆NO₁₃P

Average Molecular Weight

858.06

Monoisotopic Molecular Weight

857.505428509

IUPAC Name

(2S)-2-amino-3-({[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC

InChI Identifier

InChI=1S/C44H76NO13P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-23-27-42(49)55-32-36(33-56-59(53,54)57-34-39(45)44(51)52)58-43(50)28-24-20-19-22-26-37-38(41(48)31-40(37)47)30-29-35(46)25-21-6-4-2/h9-10,12-13,15-16,29-30,35-41,46-48H,3-8,11,14,17-28,31-34,45H2,1-2H3,(H,51,52)(H,53,54)/b10-9-,13-12-,16-15-,30-29+/t35-,36+,37+,38+,39-,40-,41+/m0/s1

InChI Key

BFVBJWAWLZXBIQ-HKYIHLRTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Diacyl-glycerol-3-phosphoserine
Glycerophosphoserine
L-alpha-amino acid
Glycerophospholipid
Alpha-amino acid or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Cyclopentanol
Cyclic alcohol
Amino acid
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

All cells and tissues (HMDB: HMDB0281830)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0281830)

Golgi apparatus membrane (HMDB: HMDB0281830)
Cell membrane (HMDB: HMDB0281830)

Source

Endogenous

Endogenous (HMDB: HMDB0281830)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylserine biosynthesis (HMDB: HMDB0281830)

Role

Biological role

Nutrient (PMID: 15979148)

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	2.42	ALOGPS
logP	6.01	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.37 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	231.66 m³·mol⁻¹	ChemAxon
Polarizability	95.35 Å³	ChemAxon
Number of Rings	1	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]+	294.001	32859911
AllCCS	[M+H-H2O]+	294.229	32859911
AllCCS	[M+Na]+	293.672	32859911
AllCCS	[M+NH4]+	293.751	32859911
AllCCS	[M-H]-	287.169	32859911
AllCCS	[M+Na-2H]-	293.867	32859911
AllCCS	[M+HCOO]-	301.219	32859911
DeepCCS	[M+H]+	284.258	30932474
DeepCCS	[M-H]-	282.362	30932474
DeepCCS	[M-2H]-	316.147	30932474
DeepCCS	[M+Na]+	290.167	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PS(18:3(6Z,9Z,12Z)/PGF1alpha)	CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC	5856.1	Standard polar	33892256
PS(18:3(6Z,9Z,12Z)/PGF1alpha)	CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC	4947.0	Standard non polar	33892256
PS(18:3(6Z,9Z,12Z)/PGF1alpha)	CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC	6215.8	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 - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 10V, Negative-QTOF	splash10-0a4i-0000000090-738f7b3aff3ef7e433a6	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 20V, Negative-QTOF	splash10-0a4i-0000000190-4640327acd2c9a6cd995	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 40V, Negative-QTOF	splash10-0aor-0133910530-239ec6cfb490c30b8e4a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 10V, Positive-QTOF	splash10-03vi-0000009990-0044d5fe8295c5a8676d	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 20V, Positive-QTOF	splash10-03vo-0900009990-774c910a27d2f67a774a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 40V, Positive-QTOF	splash10-03vo-0900009990-774c910a27d2f67a774a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 10V, Positive-QTOF	splash10-0a4i-0000001090-9260d683ff2b29ab34c1	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 20V, Positive-QTOF	splash10-05fr-0001169160-308169e540b1d8ecf5de	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 40V, Positive-QTOF	splash10-00di-0001169110-e62ad8302450957af2a0	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 10V, Positive-QTOF	splash10-001l-0000001690-d9ac0253f8cc5c50cbcc	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 20V, Positive-QTOF	splash10-001i-0000000290-a684f33cbc857672f118	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(6Z,9Z,12Z)/PGF1alpha) 40V, Positive-QTOF	splash10-0a4i-0090003310-6cbbc54d447c7348bfeb	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

156985182

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 PS(18:3(6Z,9Z,12Z)/PGF1alpha) (HMDB0281830)

MOL for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

3D MOL for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

3D SDF for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

3D-SDF for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

PDB for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

3D PDB for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

SMILES for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

INCHI for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

Structure for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

3D Structure for HMDB0281830 (PS(18:3(6Z,9Z,12Z)/PGF1alpha))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra