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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 19:13:47 UTC

Update Date

2022-11-30 19:58:23 UTC

HMDB ID

HMDB0271210

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PG(18:1(12Z)-O(9S,10R)/i-13:0)

Description

PG(18:1(12Z)-O(9S,10R)/i-13:0) is an oxidized phosphatidylglycerol (PG). Oxidized phosphatidylglycerols are glycerophospholipids in which a phosphoglycerol moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylglycerols belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PG(18:1(12Z)-O(9S,10R)/i-13:0), in particular, consists of one chain of one 9,10-epoxy-octadecenoyl at the C-1 position and one chain of 11-methyldodecanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PGs can be synthesized via three different routes. In one route, the oxidized PG is synthetized de novo following the same mechanisms as for PGs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PG backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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

PG(18:1(12Z)-O(9S,10R)/i-13:0)
  Mrv1652309122121142D          

 51 51  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    1.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6134    0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    1.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.8990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3673    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6518   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 15  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8 12  1  0  0  0  0
  8 11  1  6  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 13  1  1  0  0  0  0
 14 13  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 15 14  1  0  0  0  0
 17 38  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
M  END

HMDB0271210
     RDKit          3D
PG(18:1(12Z)-O(9S,10R)/i-13:0)
118118  0  0  0  0  0  0  0  0999 V2000
   13.4628   -5.3825   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8485   -3.9690   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0654   -3.0294    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5661   -3.1522   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9033   -2.1415    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4496   -2.2028    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6869   -1.2180    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1516    0.1249    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7563    0.4366   -1.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4692    0.4560   -1.8462 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1919    1.7774   -1.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4637    2.5930   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1756    1.9691   -0.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911    1.9383   -1.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396    1.4006   -1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494    2.1807   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3073    2.5587    1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    3.3113    1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    2.5713    1.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    1.9620    3.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    2.4394    0.9204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2550    1.7116    1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    1.6412    0.0057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4743    3.0072   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907    3.7990    0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361    5.3143   -0.3540 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.4068    5.2890   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0547    5.8809    0.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    6.4156    0.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780    6.5736    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587    7.5555    2.1618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3739    7.0166    1.9758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    8.8318    1.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    9.7560    1.7640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    1.0337    0.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792   -0.0868   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -0.6717   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2142   -0.5645    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1913   -0.3348   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5853   -0.7201   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6577   -2.1599   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2745   -3.1239   -1.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3668   -4.5254   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7613   -4.8284   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7349   -4.6666   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1639   -4.8831   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6069   -6.1895   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0492   -6.6135    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1396   -6.1068   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3618   -6.0485   -0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7521   -5.7097   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9668   -5.5126    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6298   -3.6915   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9296   -3.7695   -0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3192   -1.9823   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3288   -3.1035    1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466   -2.8365   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2508   -4.1769    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3001   -1.1384    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1626   -2.4166    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9690   -3.1720    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -1.4246    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2444    0.2863    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805    0.9209    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834    0.0923   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3523    2.2389   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1678    3.5954   -1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1096    2.8593    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720    2.3568    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4248    0.8541    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.4426   -2.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1093    3.0257   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938    0.3287   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.2721   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    3.1304   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6450   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    1.6899    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    3.3228    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5186    3.5147    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    4.3067    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.6704    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.1919    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.0740   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    3.5355   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    2.8575   -1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876    5.1698    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071    6.9006    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5259    5.5969    2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167    7.7105    3.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    7.5186    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436    9.1822    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814    8.5586    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052   10.5798    1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5246   -0.0402    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1281   -1.6716    0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.9291   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248    0.7691   -1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8361   -0.1156    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2673   -0.4594   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0564   -2.4089    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7275   -2.3912    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651   -2.9164   -1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PG(18:1(12Z)-O(9S,10R)/i-13:0)
  Mrv1652309122121142D          

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M  END
> <DATABASE_ID>
HMDB0271210

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1OC1C\C=C/CCCCC)OC(=O)CCCCCCCCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H69O11P/c1-4-5-6-7-13-18-23-34-35(48-34)24-19-14-11-16-20-25-36(40)44-29-33(30-46-49(42,43)45-28-32(39)27-38)47-37(41)26-21-15-10-8-9-12-17-22-31(2)3/h13,18,31-35,38-39H,4-12,14-17,19-30H2,1-3H3,(H,42,43)/b18-13-/t32-,33+,34?,35?/m0/s1

> <INCHI_KEY>
PSZRKAMFEVLCHE-MYJPDKKXSA-N

> <FORMULA>
C37H69O11P

> <MOLECULAR_WEIGHT>
720.922

> <EXACT_MASS>
720.45775004

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
85.02140985546693

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(11-methyldodecanoyl)oxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
6.59

> <JCHEM_LOGP>
8.673093067333333

> <ALOGPS_LOGS>
-6.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.641245576372423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907741256762458

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9689647678483633

> <JCHEM_POLAR_SURFACE_AREA>
161.35000000000002

> <JCHEM_REFRACTIVITY>
191.29300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.35e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy((2R)-2-[(11-methyldodecanoyl)oxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0271210
     RDKit          3D
PG(18:1(12Z)-O(9S,10R)/i-13:0)
118118  0  0  0  0  0  0  0  0999 V2000
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   11.3466   -2.8365   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2508   -4.1769    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3001   -1.1384    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1626   -2.4166    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9690   -3.1720    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -1.4246    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2444    0.2863    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805    0.9209    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834    0.0923   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3523    2.2389   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1678    3.5954   -1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1096    2.8593    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720    2.3568    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4248    0.8541    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.4426   -2.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1093    3.0257   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938    0.3287   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.2721   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    3.1304   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6450   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    1.6899    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    3.3228    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5186    3.5147    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    4.3067    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.6704    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.1919    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.0740   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    3.5355   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    2.8575   -1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876    5.1698    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071    6.9006    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5259    5.5969    2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167    7.7105    3.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    7.5186    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436    9.1822    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814    8.5586    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052   10.5798    1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5246   -0.0402    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1281   -1.6716    0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.9291   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248    0.7691   -1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8361   -0.1156    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2673   -0.4594   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0564   -2.4089    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7275   -2.3912    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651   -2.9164   -1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8666   -2.9261   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295   -4.6679    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0786   -5.2610   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9638   -4.2268    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7685   -5.9022    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6198   -3.5979   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4243   -5.2621   -2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7234   -4.7336   -2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4678   -4.0573   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3629   -6.9977   -1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3516   -7.4765    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9183   -7.0311    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6979   -5.7712    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5006   -5.5313   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3310   -5.6576    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4938   -7.1577   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG(18:1(12Z)-O(9S,10R)/i-13:0)                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.545   2.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.878   1.441   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.138   2.284   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       4.315   3.545   0.000  0.00  0.00           H+0
HETATM   12  O   UNK     0       2.775   3.545   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -19.087   2.876   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -23.086   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -21.214  -2.202   0.000  0.00  0.00           C+0
CONECT    1   18   13                                                       
CONECT    2   15    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12   11    9                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    1   14                                                       
CONECT   14   13   16   17   15                                             
CONECT   15    2   14                                                       
CONECT   16   14                                                            
CONECT   17   14   38                                                       
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   27   28   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   17   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  102    0
END

COMPND    HMDB0271210
HETATM    1  C1  UNL     1      13.463  -5.382  -0.384  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.848  -3.969  -0.688  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.065  -3.029   0.177  1.00  0.00           C  
HETATM    4  C4  UNL     1      11.566  -3.152  -0.036  1.00  0.00           C  
HETATM    5  C5  UNL     1      10.903  -2.141   0.896  1.00  0.00           C  
HETATM    6  C6  UNL     1       9.450  -2.203   0.746  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.687  -1.218   0.362  1.00  0.00           C  
HETATM    8  C8  UNL     1       9.152   0.125   0.009  1.00  0.00           C  
HETATM    9  C9  UNL     1       8.756   0.437  -1.425  1.00  0.00           C  
HETATM   10  O1  UNL     1       7.469   0.456  -1.846  1.00  0.00           O  
HETATM   11  C10 UNL     1       8.192   1.777  -1.676  1.00  0.00           C  
HETATM   12  C11 UNL     1       7.464   2.593  -0.675  1.00  0.00           C  
HETATM   13  C12 UNL     1       6.176   1.969  -0.206  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.191   1.938  -1.332  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.840   1.401  -1.061  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.949   2.181  -0.222  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.307   2.559   1.153  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.142   3.311   1.812  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.903   2.571   1.927  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.600   1.962   3.017  1.00  0.00           O  
HETATM   21  O3  UNL     1      -0.068   2.439   0.920  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.255   1.712   1.175  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.171   1.641   0.006  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.474   3.007  -0.599  1.00  0.00           C  
HETATM   25  O4  UNL     1      -3.191   3.799   0.305  1.00  0.00           O  
HETATM   26  P1  UNL     1      -3.536   5.314  -0.354  1.00  0.00           P  
HETATM   27  O5  UNL     1      -3.407   5.289  -1.871  1.00  0.00           O  
HETATM   28  O6  UNL     1      -5.055   5.881   0.091  1.00  0.00           O  
HETATM   29  O7  UNL     1      -2.384   6.416   0.247  1.00  0.00           O  
HETATM   30  C22 UNL     1      -2.678   6.574   1.615  1.00  0.00           C  
HETATM   31  C23 UNL     1      -1.659   7.555   2.162  1.00  0.00           C  
HETATM   32  O8  UNL     1      -0.374   7.017   1.976  1.00  0.00           O  
HETATM   33  C24 UNL     1      -1.810   8.832   1.347  1.00  0.00           C  
HETATM   34  O9  UNL     1      -0.859   9.756   1.764  1.00  0.00           O  
HETATM   35  O10 UNL     1      -3.370   1.034   0.303  1.00  0.00           O  
HETATM   36  C25 UNL     1      -3.879  -0.087  -0.290  1.00  0.00           C  
HETATM   37  O11 UNL     1      -3.271  -0.672  -1.176  1.00  0.00           O  
HETATM   38  C26 UNL     1      -5.214  -0.565   0.189  1.00  0.00           C  
HETATM   39  C27 UNL     1      -6.191  -0.335  -0.964  1.00  0.00           C  
HETATM   40  C28 UNL     1      -7.585  -0.720  -0.573  1.00  0.00           C  
HETATM   41  C29 UNL     1      -7.658  -2.160  -0.185  1.00  0.00           C  
HETATM   42  C30 UNL     1      -7.274  -3.124  -1.282  1.00  0.00           C  
HETATM   43  C31 UNL     1      -7.367  -4.525  -0.760  1.00  0.00           C  
HETATM   44  C32 UNL     1      -8.761  -4.828  -0.267  1.00  0.00           C  
HETATM   45  C33 UNL     1      -9.735  -4.667  -1.377  1.00  0.00           C  
HETATM   46  C34 UNL     1     -11.164  -4.883  -1.068  1.00  0.00           C  
HETATM   47  C35 UNL     1     -11.607  -6.189  -0.535  1.00  0.00           C  
HETATM   48  C36 UNL     1     -11.049  -6.613   0.774  1.00  0.00           C  
HETATM   49  C37 UNL     1     -13.140  -6.107  -0.396  1.00  0.00           C  
HETATM   50  H1  UNL     1      14.362  -6.049  -0.470  1.00  0.00           H  
HETATM   51  H2  UNL     1      12.752  -5.710  -1.176  1.00  0.00           H  
HETATM   52  H3  UNL     1      12.967  -5.513   0.599  1.00  0.00           H  
HETATM   53  H4  UNL     1      13.630  -3.692  -1.754  1.00  0.00           H  
HETATM   54  H5  UNL     1      14.930  -3.769  -0.516  1.00  0.00           H  
HETATM   55  H6  UNL     1      13.319  -1.982  -0.133  1.00  0.00           H  
HETATM   56  H7  UNL     1      13.329  -3.104   1.252  1.00  0.00           H  
HETATM   57  H8  UNL     1      11.347  -2.836  -1.074  1.00  0.00           H  
HETATM   58  H9  UNL     1      11.251  -4.177   0.190  1.00  0.00           H  
HETATM   59  H10 UNL     1      11.300  -1.138   0.756  1.00  0.00           H  
HETATM   60  H11 UNL     1      11.163  -2.417   1.974  1.00  0.00           H  
HETATM   61  H12 UNL     1       8.969  -3.172   0.981  1.00  0.00           H  
HETATM   62  H13 UNL     1       7.601  -1.425   0.301  1.00  0.00           H  
HETATM   63  H14 UNL     1      10.244   0.286   0.055  1.00  0.00           H  
HETATM   64  H15 UNL     1       8.680   0.921   0.653  1.00  0.00           H  
HETATM   65  H16 UNL     1       9.483   0.092  -2.215  1.00  0.00           H  
HETATM   66  H17 UNL     1       8.352   2.239  -2.686  1.00  0.00           H  
HETATM   67  H18 UNL     1       7.168   3.595  -1.099  1.00  0.00           H  
HETATM   68  H19 UNL     1       8.110   2.859   0.210  1.00  0.00           H  
HETATM   69  H20 UNL     1       5.872   2.357   0.746  1.00  0.00           H  
HETATM   70  H21 UNL     1       6.425   0.854   0.047  1.00  0.00           H  
HETATM   71  H22 UNL     1       5.651   1.443  -2.211  1.00  0.00           H  
HETATM   72  H23 UNL     1       5.109   3.026  -1.693  1.00  0.00           H  
HETATM   73  H24 UNL     1       3.894   0.329  -0.684  1.00  0.00           H  
HETATM   74  H25 UNL     1       3.317   1.272  -2.078  1.00  0.00           H  
HETATM   75  H26 UNL     1       2.654   3.130  -0.819  1.00  0.00           H  
HETATM   76  H27 UNL     1       1.922   1.645  -0.233  1.00  0.00           H  
HETATM   77  H28 UNL     1       3.525   1.690   1.771  1.00  0.00           H  
HETATM   78  H29 UNL     1       4.129   3.323   1.209  1.00  0.00           H  
HETATM   79  H30 UNL     1       2.519   3.515   2.858  1.00  0.00           H  
HETATM   80  H31 UNL     1       2.063   4.307   1.331  1.00  0.00           H  
HETATM   81  H32 UNL     1      -0.922   0.670   1.396  1.00  0.00           H  
HETATM   82  H33 UNL     1      -1.731   2.192   2.052  1.00  0.00           H  
HETATM   83  H34 UNL     1      -1.637   1.074  -0.811  1.00  0.00           H  
HETATM   84  H35 UNL     1      -1.563   3.536  -0.930  1.00  0.00           H  
HETATM   85  H36 UNL     1      -3.163   2.857  -1.477  1.00  0.00           H  
HETATM   86  H37 UNL     1      -5.688   5.170   0.311  1.00  0.00           H  
HETATM   87  H38 UNL     1      -3.707   6.901   1.786  1.00  0.00           H  
HETATM   88  H39 UNL     1      -2.526   5.597   2.147  1.00  0.00           H  
HETATM   89  H40 UNL     1      -1.817   7.711   3.234  1.00  0.00           H  
HETATM   90  H41 UNL     1       0.125   7.519   1.281  1.00  0.00           H  
HETATM   91  H42 UNL     1      -2.844   9.182   1.490  1.00  0.00           H  
HETATM   92  H43 UNL     1      -1.581   8.559   0.286  1.00  0.00           H  
HETATM   93  H44 UNL     1      -1.005  10.580   1.231  1.00  0.00           H  
HETATM   94  H45 UNL     1      -5.525  -0.040   1.092  1.00  0.00           H  
HETATM   95  H46 UNL     1      -5.128  -1.672   0.395  1.00  0.00           H  
HETATM   96  H47 UNL     1      -5.887  -0.929  -1.844  1.00  0.00           H  
HETATM   97  H48 UNL     1      -6.125   0.769  -1.188  1.00  0.00           H  
HETATM   98  H49 UNL     1      -7.836  -0.116   0.348  1.00  0.00           H  
HETATM   99  H50 UNL     1      -8.267  -0.459  -1.406  1.00  0.00           H  
HETATM  100  H51 UNL     1      -7.056  -2.409   0.702  1.00  0.00           H  
HETATM  101  H52 UNL     1      -8.727  -2.391   0.125  1.00  0.00           H  
HETATM  102  H53 UNL     1      -6.165  -2.916  -1.521  1.00  0.00           H  
HETATM  103  H54 UNL     1      -7.867  -2.926  -2.195  1.00  0.00           H  
HETATM  104  H55 UNL     1      -6.629  -4.668   0.088  1.00  0.00           H  
HETATM  105  H56 UNL     1      -7.079  -5.261  -1.552  1.00  0.00           H  
HETATM  106  H57 UNL     1      -8.964  -4.227   0.632  1.00  0.00           H  
HETATM  107  H58 UNL     1      -8.768  -5.902   0.124  1.00  0.00           H  
HETATM  108  H59 UNL     1      -9.620  -3.598  -1.753  1.00  0.00           H  
HETATM  109  H60 UNL     1      -9.424  -5.262  -2.293  1.00  0.00           H  
HETATM  110  H61 UNL     1     -11.723  -4.734  -2.049  1.00  0.00           H  
HETATM  111  H62 UNL     1     -11.468  -4.057  -0.362  1.00  0.00           H  
HETATM  112  H63 UNL     1     -11.363  -6.998  -1.276  1.00  0.00           H  
HETATM  113  H64 UNL     1     -10.352  -7.476   0.737  1.00  0.00           H  
HETATM  114  H65 UNL     1     -11.918  -7.031   1.392  1.00  0.00           H  
HETATM  115  H66 UNL     1     -10.698  -5.771   1.413  1.00  0.00           H  
HETATM  116  H67 UNL     1     -13.501  -5.531  -1.256  1.00  0.00           H  
HETATM  117  H68 UNL     1     -13.331  -5.658   0.588  1.00  0.00           H  
HETATM  118  H69 UNL     1     -13.494  -7.158  -0.381  1.00  0.00           H  
CONECT    1    2   50   51   52
CONECT    2    3   53   54
CONECT    3    4   55   56
CONECT    4    5   57   58
CONECT    5    6   59   60
CONECT    6    7    7   61
CONECT    7    8   62
CONECT    8    9   63   64
CONECT    9   10   11   65
CONECT   10   11
CONECT   11   12   66
CONECT   12   13   67   68
CONECT   13   14   69   70
CONECT   14   15   71   72
CONECT   15   16   73   74
CONECT   16   17   75   76
CONECT   17   18   77   78
CONECT   18   19   79   80
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   81   82
CONECT   23   24   35   83
CONECT   24   25   84   85
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   86
CONECT   29   30
CONECT   30   31   87   88
CONECT   31   32   33   89
CONECT   32   90
CONECT   33   34   91   92
CONECT   34   93
CONECT   35   36
CONECT   36   37   37   38
CONECT   38   39   94   95
CONECT   39   40   96   97
CONECT   40   41   98   99
CONECT   41   42  100  101
CONECT   42   43  102  103
CONECT   43   44  104  105
CONECT   44   45  106  107
CONECT   45   46  108  109
CONECT   46   47  110  111
CONECT   47   48   49  112
CONECT   48  113  114  115
CONECT   49  116  117  118
END

HMDB0271210
     RDKit          3D
PG(18:1(12Z)-O(9S,10R)/i-13:0)
118118  0  0  0  0  0  0  0  0999 V2000
   13.4628   -5.3825   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8485   -3.9690   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0654   -3.0294    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5661   -3.1522   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9033   -2.1415    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4496   -2.2028    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6869   -1.2180    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1516    0.1249    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7563    0.4366   -1.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4692    0.4560   -1.8462 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1919    1.7774   -1.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4637    2.5930   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1756    1.9691   -0.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911    1.9383   -1.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396    1.4006   -1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494    2.1807   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3073    2.5587    1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    3.3113    1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    2.5713    1.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    1.9620    3.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    2.4394    0.9204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2550    1.7116    1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    1.6412    0.0057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4743    3.0072   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907    3.7990    0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361    5.3143   -0.3540 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.4068    5.2890   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0547    5.8809    0.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    6.4156    0.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780    6.5736    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587    7.5555    2.1618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3739    7.0166    1.9758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    8.8318    1.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    9.7560    1.7640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    1.0337    0.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792   -0.0868   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -0.6717   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2142   -0.5645    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1913   -0.3348   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5853   -0.7201   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6577   -2.1599   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2745   -3.1239   -1.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3668   -4.5254   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7613   -4.8284   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7349   -4.6666   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1639   -4.8831   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6069   -6.1895   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0492   -6.6135    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1396   -6.1068   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3618   -6.0485   -0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7521   -5.7097   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9668   -5.5126    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6298   -3.6915   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9296   -3.7695   -0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3192   -1.9823   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3288   -3.1035    1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466   -2.8365   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2508   -4.1769    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3001   -1.1384    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1626   -2.4166    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9690   -3.1720    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -1.4246    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2444    0.2863    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805    0.9209    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834    0.0923   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3523    2.2389   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1678    3.5954   -1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1096    2.8593    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720    2.3568    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4248    0.8541    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.4426   -2.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1093    3.0257   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938    0.3287   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.2721   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    3.1304   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6450   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    1.6899    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    3.3228    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5186    3.5147    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    4.3067    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.6704    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.1919    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.0740   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    3.5355   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    2.8575   -1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876    5.1698    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071    6.9006    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5259    5.5969    2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167    7.7105    3.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    7.5186    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436    9.1822    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814    8.5586    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052   10.5798    1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5246   -0.0402    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1281   -1.6716    0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.9291   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248    0.7691   -1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8361   -0.1156    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2673   -0.4594   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0564   -2.4089    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7275   -2.3912    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651   -2.9164   -1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8666   -2.9261   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295   -4.6679    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0786   -5.2610   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.4243   -5.2621   -2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7234   -4.7336   -2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4678   -4.0573   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3629   -6.9977   -1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3516   -7.4765    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9183   -7.0311    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6979   -5.7712    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5006   -5.5313   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3310   -5.6576    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4938   -7.1577   -0.3814 H   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)-2,3-Dihydroxypropoxy][(2R)-2-[(11-methyldodecanoyl)oxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphinate	Generator

Chemical Formula

C₃₇H₆₉O₁₁P

Average Molecular Weight

720.922

Monoisotopic Molecular Weight

720.45775004

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(11-methyldodecanoyl)oxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-2-[(11-methyldodecanoyl)oxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1OC1C\C=C/CCCCC)OC(=O)CCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C37H69O11P/c1-4-5-6-7-13-18-23-34-35(48-34)24-19-14-11-16-20-25-36(40)44-29-33(30-46-49(42,43)45-28-32(39)27-38)47-37(41)26-21-15-10-8-9-12-17-22-31(2)3/h13,18,31-35,38-39H,4-12,14-17,19-30H2,1-3H3,(H,42,43)/b18-13-/t32-,33+,34?,35?/m0/s1

InChI Key

PSZRKAMFEVLCHE-MYJPDKKXSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.59	ALOGPS
logP	8.67	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	161.35 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	191.29 m³·mol⁻¹	ChemAxon
Polarizability	85.02 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]+	271.812	32859911
AllCCS	[M+H-H2O]+	271.597	32859911
AllCCS	[M+Na]+	272.015	32859911
AllCCS	[M+NH4]+	271.975	32859911
AllCCS	[M-H]-	259.593	32859911
AllCCS	[M+Na-2H]-	265.659	32859911
AllCCS	[M+HCOO]-	272.386	32859911
DeepCCS	[M+H]+	263.246	30932474
DeepCCS	[M-H]-	260.851	30932474
DeepCCS	[M-2H]-	294.07	30932474
DeepCCS	[M+Na]+	269.043	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PG(18:1(12Z)-O(9S,10R)/i-13:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1OC1C\C=C/CCCCC)OC(=O)CCCCCCCCCC(C)C	4537.4	Standard polar	33892256
PG(18:1(12Z)-O(9S,10R)/i-13:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1OC1C\C=C/CCCCC)OC(=O)CCCCCCCCCC(C)C	4271.3	Standard non polar	33892256
PG(18:1(12Z)-O(9S,10R)/i-13:0)	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1OC1C\C=C/CCCCC)OC(=O)CCCCCCCCCC(C)C	4863.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) 10V, Negative-QTOF	splash10-014i-0000000900-149f1caec871ef3d4557	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) 20V, Negative-QTOF	splash10-0292-0090210400-7048d71613aa2a2b3bf6	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PG(18:1(12Z)-O(9S,10R)/i-13:0) 40V, Negative-QTOF	splash10-0292-0190210400-8b5d59c2aedcf687342b	2021-09-28	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for PG(18:1(12Z)-O(9S,10R)/i-13:0) (HMDB0271210)

MOL for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

3D MOL for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

3D SDF for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

3D-SDF for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

PDB for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

3D PDB for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

SMILES for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

INCHI for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

Structure for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

3D Structure for HMDB0271210 (PG(18:1(12Z)-O(9S,10R)/i-13:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra