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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 22:52:55 UTC

Update Date

2022-11-30 19:59:13 UTC

HMDB ID

HMDB0273116

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

PGP(PGF1alpha/18:3(6Z,9Z,12Z)) is an oxidized phosphoglycerophosphate (PGP). Oxidized phosphoglycerophosphates are glycerophospholipids in which a phosphoglycerol moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphoglycerophosphates belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphoglycerophosphates can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PGP(PGF1alpha/18:3(6Z,9Z,12Z)), in particular, consists of one chain of one Prostaglandin F1alpha at the C-1 position and one chain of 6Z,9Z,12Z-octadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PGPs can be synthesized via three different routes. In one route, the oxidized PGP is synthetized de novo following the same mechanisms as for PGPs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PGP backbone, mainely through the action of LOX (PMID: 33329396 ).

Structure

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


  Mrv1652309132100532D          

 62 62  0  0  1  0            999 V2000
    5.4888    1.8388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3138    1.8388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7263    2.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5513    2.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9638    1.8388    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2494    1.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6783    2.2513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3763    1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7263    1.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3138    0.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888    0.4098    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638    0.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888    1.2348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888   -0.4152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2033   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2033   -1.6527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4888   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7744   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -2.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.4152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9806   -0.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1521   -1.5577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202    0.5769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4557    1.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132    0.4053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2999    0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284    1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415    2.3164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5261    2.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862    4.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708    4.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423    5.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9178   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322   -0.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3467   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0612   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4901   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2046   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9191   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9191   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2046   -0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2046    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9191    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6335    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3480    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3480    1.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0625    2.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0625    2.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7769    3.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7769    4.1223    0.0000 C   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  1  0  0  0  0
  5  8  2  0  0  0  0
  2  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
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 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
 19 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
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 16 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  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  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END

HMDB0273116
     RDKit          3D
PGP(PGF1alpha/18:3(6Z,9Z,12Z))
140140  0  0  0  0  0  0  0  0999 V2000
   15.1167   -3.8251    0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7366   -3.5118    1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8643   -2.9931    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4164   -1.7359   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5341   -1.2584   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4851   -2.3404   -2.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4777   -3.0032   -2.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0602   -2.7633   -2.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5321   -3.9852   -1.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9946   -4.1447   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6889   -3.2485    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782   -1.8434    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0093   -0.9063    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5867   -1.2310    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7365   -0.7893   -0.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848    0.6736   -0.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    1.4167    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444    0.9504    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -0.0263    1.4545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5823    1.5319    0.1146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605    0.9424    0.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4775    0.5122   -0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412   -0.1931   -0.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -1.3910    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -1.8083    0.6220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -2.2243    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7635   -2.3284    0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650   -2.8347   -0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374   -3.0670   -1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241   -2.0555   -1.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8490   -1.2983   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8223   -1.9765    0.1639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1988   -2.8984    1.1808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5099   -2.1257    2.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4899   -3.2820    2.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9269   -1.8565    2.3183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1550   -1.3232    3.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7030   -1.1131    0.9914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0112   -0.7580    0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5432   -1.0911   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9270   -0.6355   -1.0995 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.1720   -1.2306   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9251   -1.0121   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3028   -0.5984   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9151   -1.1560   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3503   -0.6754   -1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2286   -1.0846   -0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    2.0072    1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2995    3.0485    0.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    4.2345    1.1773 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0074    4.5458    2.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    3.5575    1.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    5.6299    0.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    6.6279    0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    7.9070    0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5535    8.2599    0.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467    9.0162    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287   10.2018   -0.0518 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   11.4059    0.6508 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4865   10.8009    1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   12.3522    1.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   12.4007   -0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5611   -4.7167    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7638   -2.9278    0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9987   -4.0636   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3432   -4.4541    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8681   -2.7763    2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8182   -3.7791   -0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8368   -2.8861    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4310   -0.9511    0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4123   -1.9151   -0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1534   -0.4019   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6003   -0.8438   -1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4976   -2.6176   -2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6380   -3.8072   -3.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0271   -1.8872   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5041   -2.6125   -3.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6287   -4.8914   -2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6800   -5.2459   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2971   -3.6813    1.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6404   -3.4910    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0234   -1.4610    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3446    0.1474    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3256   -2.2400    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2214   -0.5833    1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.1262   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961   -1.3393   -1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0285    0.8843   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065    1.1108   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7697    1.3524    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    2.5199    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
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 62140  1  0
M  END


  Mrv1652309132100532D          

 62 62  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0273116

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H78O16P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-24-28-44(50)60-38(35-59-62(54,55)58-33-37(46)32-57-61(51,52)53)34-56-43(49)27-23-20-19-22-26-39-40(42(48)31-41(39)47)30-29-36(45)25-21-6-4-2/h9-10,12-13,15-16,29-30,36-42,45-48H,3-8,11,14,17-28,31-35H2,1-2H3,(H,54,55)(H2,51,52,53)/b10-9-,13-12-,16-15-,30-29+/t36-,37-,38+,39+,40+,41-,42+/m0/s1

> <INCHI_KEY>
VAEMPLKORPVGBN-RWEXVHEPSA-N

> <FORMULA>
C44H78O16P2

> <MOLECULAR_WEIGHT>
925.04

> <EXACT_MASS>
924.476510428

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
99.59086867154093

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.75

> <JCHEM_LOGP>
7.3332511443333335

> <ALOGPS_LOGS>
-5.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.040299727526676

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3552389846760828

> <JCHEM_PKA_STRONGEST_BASIC>
-1.626766429931164

> <JCHEM_POLAR_SURFACE_AREA>
256.03999999999996

> <JCHEM_REFRACTIVITY>
241.0041000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0273116
     RDKit          3D
PGP(PGF1alpha/18:3(6Z,9Z,12Z))
140140  0  0  0  0  0  0  0  0999 V2000
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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                                  
HETATM    1  O   UNK     0      10.246   3.432   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.786   3.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.556   4.766   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.096   4.766   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      14.866   3.432   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      13.532   2.662   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      16.199   4.202   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.636   2.099   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.556   2.099   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.786   0.765   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0      10.246   0.765   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0       8.706   0.765   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.246   2.305   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.246  -0.775   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.579  -1.545   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.579  -3.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.246  -3.855   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.912  -3.085   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.578  -3.855   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.578  -5.395   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.245  -3.085   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.911  -3.855   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.577  -3.085   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.244  -3.855   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.910  -3.085   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.910  -1.545   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.424  -0.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.830  -1.401   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.151  -2.908   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.861  -0.257   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.091   1.077   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.717   2.484   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.585   0.757   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.560   1.787   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.240   3.293   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.384   4.324   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.849   3.848   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.064   5.830   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.401   6.306   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.721   7.812   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.186   8.288   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.506   9.795   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      12.913  -3.855   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      14.247  -3.085   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      14.247  -1.545   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      15.581  -3.855   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      16.914  -3.085   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.248  -3.855   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      19.582  -3.085   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      20.915  -3.855   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      22.249  -3.085   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      22.249  -1.545   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      20.915  -0.775   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      20.915   0.765   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      22.249   1.535   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      23.583   0.765   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      24.916   1.535   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      24.916   3.075   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.250   3.845   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.250   5.385   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      27.584   6.155   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      27.584   7.695   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   43                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   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   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   27   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   16   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  124    0
END

COMPND    HMDB0273116
HETATM    1  C1  UNL     1      15.117  -3.825   0.915  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.737  -3.512   1.489  1.00  0.00           C  
HETATM    3  C3  UNL     1      12.864  -2.993   0.365  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.416  -1.736  -0.249  1.00  0.00           C  
HETATM    5  C5  UNL     1      12.534  -1.258  -1.405  1.00  0.00           C  
HETATM    6  C6  UNL     1      12.485  -2.340  -2.396  1.00  0.00           C  
HETATM    7  C7  UNL     1      11.478  -3.003  -2.851  1.00  0.00           C  
HETATM    8  C8  UNL     1      10.060  -2.763  -2.410  1.00  0.00           C  
HETATM    9  C9  UNL     1       9.532  -3.985  -1.811  1.00  0.00           C  
HETATM   10  C10 UNL     1       8.995  -4.145  -0.663  1.00  0.00           C  
HETATM   11  C11 UNL     1       8.689  -3.249   0.451  1.00  0.00           C  
HETATM   12  C12 UNL     1       8.978  -1.843   0.393  1.00  0.00           C  
HETATM   13  C13 UNL     1       8.009  -0.906   0.423  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.587  -1.231   0.522  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.737  -0.789  -0.626  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.685   0.674  -0.824  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.099   1.417   0.344  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.744   0.950   0.657  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.598  -0.026   1.454  1.00  0.00           O  
HETATM   20  O2  UNL     1       2.582   1.532   0.115  1.00  0.00           O  
HETATM   21  C19 UNL     1       1.360   0.942   0.530  1.00  0.00           C  
HETATM   22  C20 UNL     1       0.477   0.512  -0.619  1.00  0.00           C  
HETATM   23  O3  UNL     1      -0.641  -0.193  -0.013  1.00  0.00           O  
HETATM   24  C21 UNL     1      -0.409  -1.391   0.630  1.00  0.00           C  
HETATM   25  O4  UNL     1       0.813  -1.808   0.622  1.00  0.00           O  
HETATM   26  C22 UNL     1      -1.377  -2.224   1.309  1.00  0.00           C  
HETATM   27  C23 UNL     1      -2.764  -2.328   0.711  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.765  -2.835  -0.677  1.00  0.00           C  
HETATM   29  C25 UNL     1      -4.037  -3.067  -1.376  1.00  0.00           C  
HETATM   30  C26 UNL     1      -5.024  -2.056  -1.638  1.00  0.00           C  
HETATM   31  C27 UNL     1      -5.849  -1.298  -0.707  1.00  0.00           C  
HETATM   32  C28 UNL     1      -6.822  -1.976   0.164  1.00  0.00           C  
HETATM   33  C29 UNL     1      -6.199  -2.898   1.181  1.00  0.00           C  
HETATM   34  O5  UNL     1      -5.510  -2.126   2.158  1.00  0.00           O  
HETATM   35  C30 UNL     1      -7.490  -3.282   2.016  1.00  0.00           C  
HETATM   36  C31 UNL     1      -7.927  -1.856   2.318  1.00  0.00           C  
HETATM   37  O6  UNL     1      -7.155  -1.323   3.321  1.00  0.00           O  
HETATM   38  C32 UNL     1      -7.703  -1.113   0.991  1.00  0.00           C  
HETATM   39  C33 UNL     1      -9.011  -0.758   0.451  1.00  0.00           C  
HETATM   40  C34 UNL     1      -9.543  -1.091  -0.694  1.00  0.00           C  
HETATM   41  C35 UNL     1     -10.927  -0.635  -1.099  1.00  0.00           C  
HETATM   42  O7  UNL     1     -11.172  -1.231  -2.340  1.00  0.00           O  
HETATM   43  C36 UNL     1     -11.925  -1.012  -0.053  1.00  0.00           C  
HETATM   44  C37 UNL     1     -13.303  -0.598  -0.369  1.00  0.00           C  
HETATM   45  C38 UNL     1     -13.915  -1.156  -1.610  1.00  0.00           C  
HETATM   46  C39 UNL     1     -15.350  -0.675  -1.790  1.00  0.00           C  
HETATM   47  C40 UNL     1     -16.229  -1.085  -0.658  1.00  0.00           C  
HETATM   48  C41 UNL     1       0.525   2.007   1.281  1.00  0.00           C  
HETATM   49  O8  UNL     1       0.300   3.048   0.376  1.00  0.00           O  
HETATM   50  P1  UNL     1      -0.628   4.234   1.177  1.00  0.00           P  
HETATM   51  O9  UNL     1       0.007   4.546   2.518  1.00  0.00           O  
HETATM   52  O10 UNL     1      -2.152   3.558   1.463  1.00  0.00           O  
HETATM   53  O11 UNL     1      -0.808   5.630   0.281  1.00  0.00           O  
HETATM   54  C42 UNL     1      -0.015   6.628   0.817  1.00  0.00           C  
HETATM   55  C43 UNL     1      -0.194   7.907   0.010  1.00  0.00           C  
HETATM   56  O12 UNL     1      -1.553   8.260   0.101  1.00  0.00           O  
HETATM   57  C44 UNL     1       0.647   9.016   0.628  1.00  0.00           C  
HETATM   58  O13 UNL     1       0.429  10.202  -0.052  1.00  0.00           O  
HETATM   59  P2  UNL     1       1.369  11.406   0.651  1.00  0.00           P  
HETATM   60  O14 UNL     1       2.487  10.801   1.480  1.00  0.00           O  
HETATM   61  O15 UNL     1       0.364  12.352   1.642  1.00  0.00           O  
HETATM   62  O16 UNL     1       2.095  12.401  -0.527  1.00  0.00           O  
HETATM   63  H1  UNL     1      15.561  -4.717   1.417  1.00  0.00           H  
HETATM   64  H2  UNL     1      15.764  -2.928   0.990  1.00  0.00           H  
HETATM   65  H3  UNL     1      14.999  -4.064  -0.167  1.00  0.00           H  
HETATM   66  H4  UNL     1      13.343  -4.454   1.912  1.00  0.00           H  
HETATM   67  H5  UNL     1      13.868  -2.776   2.304  1.00  0.00           H  
HETATM   68  H6  UNL     1      12.818  -3.779  -0.445  1.00  0.00           H  
HETATM   69  H7  UNL     1      11.837  -2.886   0.737  1.00  0.00           H  
HETATM   70  H8  UNL     1      13.431  -0.951   0.539  1.00  0.00           H  
HETATM   71  H9  UNL     1      14.412  -1.915  -0.687  1.00  0.00           H  
HETATM   72  H10 UNL     1      13.153  -0.402  -1.851  1.00  0.00           H  
HETATM   73  H11 UNL     1      11.600  -0.844  -1.085  1.00  0.00           H  
HETATM   74  H12 UNL     1      13.498  -2.618  -2.807  1.00  0.00           H  
HETATM   75  H13 UNL     1      11.638  -3.807  -3.615  1.00  0.00           H  
HETATM   76  H14 UNL     1      10.027  -1.887  -1.795  1.00  0.00           H  
HETATM   77  H15 UNL     1       9.504  -2.612  -3.387  1.00  0.00           H  
HETATM   78  H16 UNL     1       9.629  -4.891  -2.480  1.00  0.00           H  
HETATM   79  H17 UNL     1       8.680  -5.246  -0.461  1.00  0.00           H  
HETATM   80  H18 UNL     1       9.297  -3.681   1.356  1.00  0.00           H  
HETATM   81  H19 UNL     1       7.640  -3.491   0.799  1.00  0.00           H  
HETATM   82  H20 UNL     1      10.023  -1.461   0.377  1.00  0.00           H  
HETATM   83  H21 UNL     1       8.345   0.147   0.371  1.00  0.00           H  
HETATM   84  H22 UNL     1       6.326  -2.240   0.859  1.00  0.00           H  
HETATM   85  H23 UNL     1       6.221  -0.583   1.409  1.00  0.00           H  
HETATM   86  H24 UNL     1       4.684  -1.126  -0.384  1.00  0.00           H  
HETATM   87  H25 UNL     1       5.996  -1.339  -1.567  1.00  0.00           H  
HETATM   88  H26 UNL     1       5.029   0.884  -1.712  1.00  0.00           H  
HETATM   89  H27 UNL     1       6.707   1.111  -1.032  1.00  0.00           H  
HETATM   90  H28 UNL     1       5.770   1.352   1.201  1.00  0.00           H  
HETATM   91  H29 UNL     1       5.058   2.520   0.074  1.00  0.00           H  
HETATM   92  H30 UNL     1       1.551   0.134   1.222  1.00  0.00           H  
HETATM   93  H31 UNL     1       1.033  -0.250  -1.184  1.00  0.00           H  
HETATM   94  H32 UNL     1       0.131   1.356  -1.216  1.00  0.00           H  
HETATM   95  H33 UNL     1      -0.946  -3.273   1.435  1.00  0.00           H  
HETATM   96  H34 UNL     1      -1.497  -1.917   2.408  1.00  0.00           H  
HETATM   97  H35 UNL     1      -3.259  -3.117   1.355  1.00  0.00           H  
HETATM   98  H36 UNL     1      -3.242  -1.359   0.781  1.00  0.00           H  
HETATM   99  H37 UNL     1      -2.242  -3.851  -0.634  1.00  0.00           H  
HETATM  100  H38 UNL     1      -2.036  -2.254  -1.335  1.00  0.00           H  
HETATM  101  H39 UNL     1      -3.692  -3.438  -2.438  1.00  0.00           H  
HETATM  102  H40 UNL     1      -4.464  -4.055  -1.001  1.00  0.00           H  
HETATM  103  H41 UNL     1      -5.798  -2.559  -2.365  1.00  0.00           H  
HETATM  104  H42 UNL     1      -4.546  -1.258  -2.331  1.00  0.00           H  
HETATM  105  H43 UNL     1      -5.246  -0.521  -0.114  1.00  0.00           H  
HETATM  106  H44 UNL     1      -6.471  -0.573  -1.363  1.00  0.00           H  
HETATM  107  H45 UNL     1      -7.460  -2.619  -0.544  1.00  0.00           H  
HETATM  108  H46 UNL     1      -5.753  -3.793   0.892  1.00  0.00           H  
HETATM  109  H47 UNL     1      -5.308  -2.716   2.916  1.00  0.00           H  
HETATM  110  H48 UNL     1      -8.140  -3.807   1.326  1.00  0.00           H  
HETATM  111  H49 UNL     1      -7.152  -3.833   2.906  1.00  0.00           H  
HETATM  112  H50 UNL     1      -9.001  -1.892   2.543  1.00  0.00           H  
HETATM  113  H51 UNL     1      -7.674  -1.057   4.128  1.00  0.00           H  
HETATM  114  H52 UNL     1      -7.156  -0.180   1.262  1.00  0.00           H  
HETATM  115  H53 UNL     1      -9.647  -0.115   1.104  1.00  0.00           H  
HETATM  116  H54 UNL     1      -8.971  -1.706  -1.371  1.00  0.00           H  
HETATM  117  H55 UNL     1     -10.956   0.461  -1.238  1.00  0.00           H  
HETATM  118  H56 UNL     1     -11.429  -2.168  -2.172  1.00  0.00           H  
HETATM  119  H57 UNL     1     -11.839  -2.091   0.240  1.00  0.00           H  
HETATM  120  H58 UNL     1     -11.624  -0.460   0.886  1.00  0.00           H  
HETATM  121  H59 UNL     1     -13.319   0.536  -0.389  1.00  0.00           H  
HETATM  122  H60 UNL     1     -13.937  -0.849   0.535  1.00  0.00           H  
HETATM  123  H61 UNL     1     -13.958  -2.259  -1.520  1.00  0.00           H  
HETATM  124  H62 UNL     1     -13.386  -0.796  -2.519  1.00  0.00           H  
HETATM  125  H63 UNL     1     -15.780  -1.022  -2.741  1.00  0.00           H  
HETATM  126  H64 UNL     1     -15.376   0.452  -1.843  1.00  0.00           H  
HETATM  127  H65 UNL     1     -15.723  -1.845  -0.010  1.00  0.00           H  
HETATM  128  H66 UNL     1     -17.131  -1.584  -1.065  1.00  0.00           H  
HETATM  129  H67 UNL     1     -16.616  -0.229  -0.055  1.00  0.00           H  
HETATM  130  H68 UNL     1      -0.407   1.566   1.636  1.00  0.00           H  
HETATM  131  H69 UNL     1       1.122   2.373   2.158  1.00  0.00           H  
HETATM  132  H70 UNL     1      -2.575   3.956   2.243  1.00  0.00           H  
HETATM  133  H71 UNL     1      -0.299   6.796   1.861  1.00  0.00           H  
HETATM  134  H72 UNL     1       1.083   6.386   0.756  1.00  0.00           H  
HETATM  135  H73 UNL     1       0.135   7.768  -1.027  1.00  0.00           H  
HETATM  136  H74 UNL     1      -1.888   8.416  -0.812  1.00  0.00           H  
HETATM  137  H75 UNL     1       0.353   9.122   1.685  1.00  0.00           H  
HETATM  138  H76 UNL     1       1.715   8.730   0.525  1.00  0.00           H  
HETATM  139  H77 UNL     1      -0.319  11.756   2.040  1.00  0.00           H  
HETATM  140  H78 UNL     1       2.881  11.923  -0.876  1.00  0.00           H  
CONECT    1    2   63   64   65
CONECT    2    3   66   67
CONECT    3    4   68   69
CONECT    4    5   70   71
CONECT    5    6   72   73
CONECT    6    7    7   74
CONECT    7    8   75
CONECT    8    9   76   77
CONECT    9   10   10   78
CONECT   10   11   79
CONECT   11   12   80   81
CONECT   12   13   13   82
CONECT   13   14   83
CONECT   14   15   84   85
CONECT   15   16   86   87
CONECT   16   17   88   89
CONECT   17   18   90   91
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   48   92
CONECT   22   23   93   94
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   95   96
CONECT   27   28   97   98
CONECT   28   29   99  100
CONECT   29   30  101  102
CONECT   30   31  103  104
CONECT   31   32  105  106
CONECT   32   33   38  107
CONECT   33   34   35  108
CONECT   34  109
CONECT   35   36  110  111
CONECT   36   37   38  112
CONECT   37  113
CONECT   38   39  114
CONECT   39   40   40  115
CONECT   40   41  116
CONECT   41   42   43  117
CONECT   42  118
CONECT   43   44  119  120
CONECT   44   45  121  122
CONECT   45   46  123  124
CONECT   46   47  125  126
CONECT   47  127  128  129
CONECT   48   49  130  131
CONECT   49   50
CONECT   50   51   51   52   53
CONECT   52  132
CONECT   53   54
CONECT   54   55  133  134
CONECT   55   56   57  135
CONECT   56  136
CONECT   57   58  137  138
CONECT   58   59
CONECT   59   60   60   61   62
CONECT   61  139
CONECT   62  140
END

HMDB0273116
     RDKit          3D
PGP(PGF1alpha/18:3(6Z,9Z,12Z))
140140  0  0  0  0  0  0  0  0999 V2000
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M  END

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Synonyms

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

Chemical Formula

C₄₄H₇₈O₁₆P₂

Average Molecular Weight

925.04

Monoisotopic Molecular Weight

924.476510428

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H78O16P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-24-28-44(50)60-38(35-59-62(54,55)58-33-37(46)32-57-61(51,52)53)34-56-43(49)27-23-20-19-22-26-39-40(42(48)31-41(39)47)30-29-36(45)25-21-6-4-2/h9-10,12-13,15-16,29-30,36-42,45-48H,3-8,11,14,17-28,31-35H2,1-2H3,(H,54,55)(H2,51,52,53)/b10-9-,13-12-,16-15-,30-29+/t36-,37-,38+,39+,40+,41-,42+/m0/s1

InChI Key

VAEMPLKORPVGBN-RWEXVHEPSA-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
Diacylglycerophosphoglycerophosphate
Glycerophospholipid
Sn-glycerol-3-phosphate
Dialkyl phosphate
Monoalkyl phosphate
Fatty acid ester
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclopentanol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0273116)

Process

Not Available

Role

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	4.75	ALOGPS
logP	7.33	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	241 m³·mol⁻¹	ChemAxon
Polarizability	99.59 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]+	302.157	32859911
AllCCS	[M+H-H2O]+	302.5	32859911
AllCCS	[M+Na]+	301.693	32859911
AllCCS	[M+NH4]+	301.802	32859911
AllCCS	[M-H]-	296.612	32859911
AllCCS	[M+Na-2H]-	303.445	32859911
AllCCS	[M+HCOO]-	310.916	32859911
DeepCCS	[M+H]+	305.644	30932474
DeepCCS	[M-H]-	303.749	30932474
DeepCCS	[M-2H]-	337.138	30932474
DeepCCS	[M+Na]+	311.422	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.16 minutes	32390414
Predicted by Siyang on May 30, 2022	20.3218 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4318.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	155.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	276.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	500.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1095.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	836.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	694.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1953.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	973.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1834.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	684.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	570.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	323.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	86.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.1 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF	splash10-0a4i-0000005093-67745a01daa2ebefe1a2	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF	splash10-0a4i-2120002391-16824eb9308cae848217	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF	splash10-067j-6401902700-2ed55da6e7d9b1d3faa5	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF	splash10-00di-0000000019-3ca1a6e428e4b0a217ec	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF	splash10-004i-9022016124-3347f377a2bc82a93357	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(PGF1alpha/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF	splash10-004i-9033011000-433d000fa6974e396b35	2021-10-19	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156976468

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for PGP(PGF1alpha/18:3(6Z,9Z,12Z)) (HMDB0273116)

MOL for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

3D MOL for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

3D SDF for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

3D-SDF for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

PDB for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

3D PDB for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

SMILES for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

INCHI for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

Structure for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

3D Structure for HMDB0273116 (PGP(PGF1alpha/18:3(6Z,9Z,12Z)))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra