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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-13 06:23:46 UTC

Update Date

2022-11-30 20:00:54 UTC

HMDB ID

HMDB0276779

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PI(18:3(6Z,9Z,12Z)/PGE2)

Description

PI(18:3(6Z,9Z,12Z)/PGE2) is an oxidized phosphatidylinositol (PI). Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PI(18:3(6Z,9Z,12Z)/PGE2), in particular, consists of one chain of 6Z,9Z,12Z-octadecatrienoyl at the C-1 position and one chain of Prostaglandin E2 at the C-2 position. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.

Structure

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


  Mrv1652309132108242D          

 64 65  0  0  1  0            999 V2000
    0.2520   -1.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199   -0.9456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0154   -0.1950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9036   -0.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2572    0.6300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1673    0.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    1.4662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2377    2.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.9583    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350    3.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5157    3.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    3.1008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9164    2.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    2.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2053    3.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313    3.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    3.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169    4.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837    3.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788    4.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8676    3.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1951    3.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0166    2.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6247    3.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4279    4.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0234    4.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267    5.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345    5.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8377    6.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455    6.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500    6.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578    6.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623    6.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    6.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746    5.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    1.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909    1.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7382    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884   -0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526   -1.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -2.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549   -2.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3174   -1.7979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1647   -1.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -2.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036   -0.3068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6727    0.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4248    0.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2283    0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130   -1.5273    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8390   -2.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972   -1.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285   -1.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238   -1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1114   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8801   -1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468    1.3864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3135    2.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710    0.9628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2457    0.9430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 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  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 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
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  2 45  1  0  0  0  0
 45 46  1  1  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  0  0  0  0
 51 52  1  1  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  6  0  0  0
 54 56  1  0  0  0  0
 56 57  1  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
  7 61  1  0  0  0  0
 61 62  1  6  0  0  0
 61 63  1  0  0  0  0
 51 63  1  0  0  0  0
 63 64  1  6  0  0  0
M  END

HMDB0276779
     RDKit          3D
PI(18:3(6Z,9Z,12Z)/PGE2)
141142  0  0  0  0  0  0  0  0999 V2000
   16.8881   -0.6621    2.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3528    0.6052    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1256    1.0890    2.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9989    0.0887    2.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5577   -0.2600    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1020    0.9195    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9168    1.1026   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8215    0.1117   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6783    0.7319    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4935    0.9204   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2332    0.4910   -1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    1.6783   -2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442    1.8503   -2.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446    0.8340   -2.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    0.3857   -4.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794   -0.6077   -4.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9298   -0.2205   -4.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.0069   -2.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.6309   -1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.9232   -2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035    1.2942   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    0.2528   -0.1456 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3399    0.9096    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    0.4591    1.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8365    1.6846    2.2505 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.4098    2.5685    1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    2.7379    3.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126    1.0857    3.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292    0.3219    2.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4863   -1.0194    2.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4480   -1.1621    3.2260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.7075    1.0422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5251   -3.0816    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -1.2072   -0.3143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4492    0.1534   -0.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -1.8398   -1.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0746   -3.0953   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -2.6847   -2.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9174   -2.9427   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -4.1460   -2.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899   -3.8364   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -2.6366   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.1798   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -3.0023    0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.8673    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6708   -2.0155   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9945   -3.1137    0.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -0.8676    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.0944    1.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8998   -2.1656    2.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6357    0.1551    2.1511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7234    0.8654    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7220    2.1175    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9148    2.7203    0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0211    2.2048   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1074    2.5946    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3674    3.1287    0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9484    2.5036   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4427    1.1171   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5342    0.0137   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680    1.0125    2.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0021    2.1156    3.1919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3374    0.4001    3.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6183   -0.8038    3.8278 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3456   -1.5610    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9597   -0.7589    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7875   -0.5766    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1368    0.4301    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1457    1.3974    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3923    1.2562    3.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7759    2.0746    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1581    0.5286    2.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3537   -0.8322    2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4828   -0.7108    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8509   -1.0798    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8276    1.7429   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7002    2.0498   -0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1506   -0.7183    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6295   -0.3857   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8569    1.0533    1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6825    1.3827    0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4160   -0.2480   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762   -0.0395   -2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6178    2.4788   -2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309132108242D          

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M  END
> <DATABASE_ID>
HMDB0276779

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@@H]1COP(O)(=O)O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C\C=C/CCCC(=O)O1)C(=O)C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@H](O)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C47H77O16P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-23-27-40(51)60-32-35-33-61-64(58,59)63-47-45(56)43(54)37(30-29-34(48)25-21-6-4-2)39(50)31-38(49)36(42(53)44(55)46(47)57)26-22-19-20-24-28-41(52)62-35/h9-10,12-13,15-16,19,22,29-30,34-37,39,42-48,50,53-57H,3-8,11,14,17-18,20-21,23-28,31-33H2,1-2H3,(H,58,59)/b10-9-,13-12-,16-15-,22-19-,30-29+/t34-,35+,36-,37-,39+,42+,43+,44-,45+,46+,47+/m0/s1

> <INCHI_KEY>
XBVMAPFCARIVAP-HGWYJPIFSA-N

> <FORMULA>
C47H77O16P

> <MOLECULAR_WEIGHT>
929.091

> <EXACT_MASS>
928.494923397

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
100.01346295624901

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,6R,12Z,15R,18R,19S,20R,21R,22R,23S,24R)-3,18,20,21,22,23,24-heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,16-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
5.651764876333334

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.55299119086769

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8334189273207464

> <JCHEM_PKA_STRONGEST_BASIC>
-1.626486710885005

> <JCHEM_POLAR_SURFACE_AREA>
267.03999999999996

> <JCHEM_REFRACTIVITY>
245.5263000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,6R,12Z,15R,18R,19S,20R,21R,22R,23S,24R)-3,18,20,21,22,23,24-heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,16-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0276779
     RDKit          3D
PI(18:3(6Z,9Z,12Z)/PGE2)
141142  0  0  0  0  0  0  0  0999 V2000
   16.8881   -0.6621    2.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3528    0.6052    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1256    1.0890    2.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9989    0.0887    2.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5577   -0.2600    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1020    0.9195    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9168    1.1026   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8215    0.1117   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6783    0.7319    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4935    0.9204   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2332    0.4910   -1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    1.6783   -2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442    1.8503   -2.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446    0.8340   -2.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    0.3857   -4.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794   -0.6077   -4.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9298   -0.2205   -4.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.0069   -2.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.6309   -1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.9232   -2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035    1.2942   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    0.2528   -0.1456 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3399    0.9096    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    0.4591    1.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8365    1.6846    2.2505 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.4098    2.5685    1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    2.7379    3.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126    1.0857    3.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292    0.3219    2.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4863   -1.0194    2.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4480   -1.1621    3.2260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.7075    1.0422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5251   -3.0816    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -1.2072   -0.3143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4492    0.1534   -0.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -1.8398   -1.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0746   -3.0953   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -2.6847   -2.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9174   -2.9427   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -4.1460   -2.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899   -3.8364   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -2.6366   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.1798   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -3.0023    0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.8673    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6708   -2.0155   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9945   -3.1137    0.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -0.8676    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.0944    1.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8998   -2.1656    2.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6357    0.1551    2.1511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7234    0.8654    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7220    2.1175    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9148    2.7203    0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0211    2.2048   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1074    2.5946    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3674    3.1287    0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9484    2.5036   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4427    1.1171   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5342    0.0137   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680    1.0125    2.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0021    2.1156    3.1919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3374    0.4001    3.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6183   -0.8038    3.8278 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3456   -1.5610    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9597   -0.7589    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7875   -0.5766    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1368    0.4301    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1457    1.3974    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3923    1.2562    3.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7759    2.0746    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1581    0.5286    2.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3537   -0.8322    2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4828   -0.7108    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8509   -1.0798    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8276    1.7429   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7002    2.0498   -0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1506   -0.7183    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6295   -0.3857   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8569    1.0533    1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6825    1.3827    0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4160   -0.2480   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762   -0.0395   -2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6178    2.4788   -2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734    2.7771   -3.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8084    0.0284   -2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311    1.4123   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001   -0.0944   -4.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1423    1.2821   -5.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -1.5658   -3.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1699   -0.9552   -5.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.7190   -4.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -0.9747   -4.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    1.6231   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.2351   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465   -0.0221   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1166    0.6713    1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465    2.0031    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    2.4415    4.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1883    0.9511    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837   -1.6936    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -2.0880    3.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -1.9365    1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841   -3.4722    1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -1.4483   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607    0.3077   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7807   -1.1256   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -3.8063   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107   -3.4924   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -2.1655   -3.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -2.2910   -3.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -4.9028   -2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400   -4.6573   -2.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -3.7321   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -4.6990   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -1.7570   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -2.9275   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9037    0.0137    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047   -0.7082   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3922   -1.4285    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4789   -2.9517    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0531   -0.1919    3.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6324    0.2813    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8595    2.7224    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7155    3.8145    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9377   -0.9487    4.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 13-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-21         0                                  
HETATM    1  O   UNK     0       0.470  -2.574   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.784  -1.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.895  -0.364   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.553  -0.574   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.347   1.176   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.046   1.172   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.030   2.737   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.310   4.291   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0      -1.345   5.522   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0      -1.372   7.167   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.829   6.238   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.207   5.788   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.711   5.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.138   4.631   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.117   5.961   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.658   6.398   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.853   7.442   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.192   8.873   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.370   6.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.481   8.063   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.953   7.457   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.564   5.961   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.098   5.538   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.233   6.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.865   8.122   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.977   9.187   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.610  10.683   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.131  11.113   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.764  12.608   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.285  13.038   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.173  11.972   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.695  12.402   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.583  11.336   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.104  11.766   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.993  10.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.072   3.344   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.761   1.917   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.330   2.341   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.111   0.376   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.392  -1.163   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.765  -2.795   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.678  -3.751   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.256  -4.443   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.662  -4.371   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.593  -3.356   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.174  -3.239   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -3.201  -4.542   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.948  -1.666   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -0.567  -0.573   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.256   1.000   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       0.793   0.247   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.293   0.003   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.641  -1.507   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.384  -2.851   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       3.433  -4.761   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       4.848  -1.938   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.587  -2.399   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.258  -2.246   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.541  -3.274   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.976  -2.715   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -0.461   2.588   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -0.585   4.074   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       0.879   1.797   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       2.325   1.760   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   45                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   61                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   14   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    2   46                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   63                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59                                                            
CONECT   61    7   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   51   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  130    0
END

COMPND    HMDB0276779
HETATM    1  C1  UNL     1      16.888  -0.662   2.164  1.00  0.00           C  
HETATM    2  C2  UNL     1      16.353   0.605   1.525  1.00  0.00           C  
HETATM    3  C3  UNL     1      15.126   1.089   2.230  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.999   0.089   2.212  1.00  0.00           C  
HETATM    5  C5  UNL     1      13.558  -0.260   0.785  1.00  0.00           C  
HETATM    6  C6  UNL     1      13.102   0.920   0.063  1.00  0.00           C  
HETATM    7  C7  UNL     1      11.917   1.103  -0.434  1.00  0.00           C  
HETATM    8  C8  UNL     1      10.821   0.112  -0.334  1.00  0.00           C  
HETATM    9  C9  UNL     1       9.678   0.732   0.371  1.00  0.00           C  
HETATM   10  C10 UNL     1       8.493   0.920  -0.145  1.00  0.00           C  
HETATM   11  C11 UNL     1       8.233   0.491  -1.558  1.00  0.00           C  
HETATM   12  C12 UNL     1       7.855   1.678  -2.369  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.744   1.850  -2.999  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.645   0.834  -2.993  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.364   0.386  -4.382  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.279  -0.608  -4.515  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.930  -0.220  -4.061  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.719  -0.007  -2.626  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.347  -0.631  -1.756  1.00  0.00           O  
HETATM   20  O2  UNL     1       1.789   0.923  -2.235  1.00  0.00           O  
HETATM   21  C19 UNL     1       1.403   1.294  -0.964  1.00  0.00           C  
HETATM   22  C20 UNL     1       0.712   0.253  -0.146  1.00  0.00           C  
HETATM   23  C21 UNL     1       0.340   0.910   1.186  1.00  0.00           C  
HETATM   24  O3  UNL     1      -0.875   0.459   1.656  1.00  0.00           O  
HETATM   25  P1  UNL     1      -1.836   1.685   2.250  1.00  0.00           P  
HETATM   26  O4  UNL     1      -2.410   2.568   1.142  1.00  0.00           O  
HETATM   27  O5  UNL     1      -0.967   2.738   3.261  1.00  0.00           O  
HETATM   28  O6  UNL     1      -3.113   1.086   3.164  1.00  0.00           O  
HETATM   29  C22 UNL     1      -4.029   0.322   2.384  1.00  0.00           C  
HETATM   30  C23 UNL     1      -3.486  -1.019   2.256  1.00  0.00           C  
HETATM   31  O7  UNL     1      -2.448  -1.162   3.226  1.00  0.00           O  
HETATM   32  C24 UNL     1      -3.111  -1.707   1.042  1.00  0.00           C  
HETATM   33  O8  UNL     1      -3.525  -3.082   1.039  1.00  0.00           O  
HETATM   34  C25 UNL     1      -3.308  -1.207  -0.314  1.00  0.00           C  
HETATM   35  O9  UNL     1      -3.449   0.153  -0.490  1.00  0.00           O  
HETATM   36  C26 UNL     1      -4.467  -1.840  -1.061  1.00  0.00           C  
HETATM   37  C27 UNL     1      -4.075  -3.095  -1.802  1.00  0.00           C  
HETATM   38  C28 UNL     1      -3.209  -2.685  -2.934  1.00  0.00           C  
HETATM   39  C29 UNL     1      -1.917  -2.943  -2.925  1.00  0.00           C  
HETATM   40  C30 UNL     1      -1.412  -4.146  -2.241  1.00  0.00           C  
HETATM   41  C31 UNL     1      -0.490  -3.836  -1.081  1.00  0.00           C  
HETATM   42  C32 UNL     1       0.360  -2.637  -1.327  1.00  0.00           C  
HETATM   43  C33 UNL     1       1.079  -2.180  -0.122  1.00  0.00           C  
HETATM   44  O10 UNL     1       1.311  -3.002   0.795  1.00  0.00           O  
HETATM   45  O11 UNL     1       1.512  -0.867   0.039  1.00  0.00           O  
HETATM   46  C34 UNL     1      -5.671  -2.015  -0.245  1.00  0.00           C  
HETATM   47  O12 UNL     1      -5.994  -3.114   0.163  1.00  0.00           O  
HETATM   48  C35 UNL     1      -6.559  -0.868   0.127  1.00  0.00           C  
HETATM   49  C36 UNL     1      -7.368  -1.094   1.349  1.00  0.00           C  
HETATM   50  O13 UNL     1      -6.900  -2.166   2.064  1.00  0.00           O  
HETATM   51  C37 UNL     1      -7.636   0.155   2.151  1.00  0.00           C  
HETATM   52  C38 UNL     1      -8.723   0.865   1.458  1.00  0.00           C  
HETATM   53  C39 UNL     1      -8.722   2.117   1.071  1.00  0.00           C  
HETATM   54  C40 UNL     1      -9.915   2.720   0.370  1.00  0.00           C  
HETATM   55  O14 UNL     1     -10.021   2.205  -0.878  1.00  0.00           O  
HETATM   56  C41 UNL     1     -11.107   2.595   1.275  1.00  0.00           C  
HETATM   57  C42 UNL     1     -12.367   3.129   0.716  1.00  0.00           C  
HETATM   58  C43 UNL     1     -12.948   2.504  -0.487  1.00  0.00           C  
HETATM   59  C44 UNL     1     -13.443   1.117  -0.409  1.00  0.00           C  
HETATM   60  C45 UNL     1     -12.534   0.014  -0.051  1.00  0.00           C  
HETATM   61  C46 UNL     1      -6.468   1.012   2.445  1.00  0.00           C  
HETATM   62  O15 UNL     1      -7.002   2.116   3.192  1.00  0.00           O  
HETATM   63  C47 UNL     1      -5.337   0.400   3.203  1.00  0.00           C  
HETATM   64  O16 UNL     1      -5.618  -0.804   3.828  1.00  0.00           O  
HETATM   65  H1  UNL     1      16.346  -1.561   1.830  1.00  0.00           H  
HETATM   66  H2  UNL     1      17.960  -0.759   1.896  1.00  0.00           H  
HETATM   67  H3  UNL     1      16.788  -0.577   3.283  1.00  0.00           H  
HETATM   68  H4  UNL     1      16.137   0.430   0.457  1.00  0.00           H  
HETATM   69  H5  UNL     1      17.146   1.397   1.551  1.00  0.00           H  
HETATM   70  H6  UNL     1      15.392   1.256   3.297  1.00  0.00           H  
HETATM   71  H7  UNL     1      14.776   2.075   1.834  1.00  0.00           H  
HETATM   72  H8  UNL     1      13.158   0.529   2.782  1.00  0.00           H  
HETATM   73  H9  UNL     1      14.354  -0.832   2.715  1.00  0.00           H  
HETATM   74  H10 UNL     1      14.483  -0.711   0.309  1.00  0.00           H  
HETATM   75  H11 UNL     1      12.851  -1.080   0.836  1.00  0.00           H  
HETATM   76  H12 UNL     1      13.828   1.743  -0.080  1.00  0.00           H  
HETATM   77  H13 UNL     1      11.700   2.050  -0.965  1.00  0.00           H  
HETATM   78  H14 UNL     1      11.151  -0.718   0.378  1.00  0.00           H  
HETATM   79  H15 UNL     1      10.630  -0.386  -1.268  1.00  0.00           H  
HETATM   80  H16 UNL     1       9.857   1.053   1.414  1.00  0.00           H  
HETATM   81  H17 UNL     1       7.682   1.383   0.421  1.00  0.00           H  
HETATM   82  H18 UNL     1       7.416  -0.248  -1.505  1.00  0.00           H  
HETATM   83  H19 UNL     1       9.076  -0.039  -2.026  1.00  0.00           H  
HETATM   84  H20 UNL     1       8.618   2.479  -2.425  1.00  0.00           H  
HETATM   85  H21 UNL     1       6.573   2.777  -3.572  1.00  0.00           H  
HETATM   86  H22 UNL     1       5.808   0.028  -2.288  1.00  0.00           H  
HETATM   87  H23 UNL     1       4.731   1.412  -2.656  1.00  0.00           H  
HETATM   88  H24 UNL     1       6.300  -0.094  -4.814  1.00  0.00           H  
HETATM   89  H25 UNL     1       5.142   1.282  -5.028  1.00  0.00           H  
HETATM   90  H26 UNL     1       4.580  -1.566  -3.986  1.00  0.00           H  
HETATM   91  H27 UNL     1       4.170  -0.955  -5.585  1.00  0.00           H  
HETATM   92  H28 UNL     1       2.655   0.719  -4.631  1.00  0.00           H  
HETATM   93  H29 UNL     1       2.162  -0.975  -4.401  1.00  0.00           H  
HETATM   94  H30 UNL     1       2.327   1.623  -0.383  1.00  0.00           H  
HETATM   95  H31 UNL     1       0.792   2.235  -1.017  1.00  0.00           H  
HETATM   96  H32 UNL     1      -0.247  -0.022  -0.679  1.00  0.00           H  
HETATM   97  H33 UNL     1       1.117   0.671   1.954  1.00  0.00           H  
HETATM   98  H34 UNL     1       0.347   2.003   1.056  1.00  0.00           H  
HETATM   99  H35 UNL     1      -1.060   2.441   4.182  1.00  0.00           H  
HETATM  100  H36 UNL     1      -4.188   0.951   1.518  1.00  0.00           H  
HETATM  101  H37 UNL     1      -4.284  -1.694   2.744  1.00  0.00           H  
HETATM  102  H38 UNL     1      -2.116  -2.088   3.206  1.00  0.00           H  
HETATM  103  H39 UNL     1      -1.987  -1.936   1.115  1.00  0.00           H  
HETATM  104  H40 UNL     1      -3.484  -3.472   1.917  1.00  0.00           H  
HETATM  105  H41 UNL     1      -2.423  -1.448  -0.994  1.00  0.00           H  
HETATM  106  H42 UNL     1      -3.761   0.308  -1.411  1.00  0.00           H  
HETATM  107  H43 UNL     1      -4.781  -1.126  -1.891  1.00  0.00           H  
HETATM  108  H44 UNL     1      -3.608  -3.806  -1.120  1.00  0.00           H  
HETATM  109  H45 UNL     1      -5.011  -3.492  -2.260  1.00  0.00           H  
HETATM  110  H46 UNL     1      -3.626  -2.166  -3.784  1.00  0.00           H  
HETATM  111  H47 UNL     1      -1.183  -2.291  -3.416  1.00  0.00           H  
HETATM  112  H48 UNL     1      -2.169  -4.903  -2.002  1.00  0.00           H  
HETATM  113  H49 UNL     1      -0.740  -4.657  -3.000  1.00  0.00           H  
HETATM  114  H50 UNL     1      -1.105  -3.732  -0.179  1.00  0.00           H  
HETATM  115  H51 UNL     1       0.198  -4.699  -0.909  1.00  0.00           H  
HETATM  116  H52 UNL     1      -0.180  -1.757  -1.734  1.00  0.00           H  
HETATM  117  H53 UNL     1       1.107  -2.927  -2.127  1.00  0.00           H  
HETATM  118  H54 UNL     1      -5.904   0.014   0.148  1.00  0.00           H  
HETATM  119  H55 UNL     1      -7.205  -0.708  -0.789  1.00  0.00           H  
HETATM  120  H56 UNL     1      -8.392  -1.428   0.980  1.00  0.00           H  
HETATM  121  H57 UNL     1      -7.479  -2.952   2.086  1.00  0.00           H  
HETATM  122  H58 UNL     1      -8.053  -0.192   3.137  1.00  0.00           H  
HETATM  123  H59 UNL     1      -9.632   0.281   1.245  1.00  0.00           H  
HETATM  124  H60 UNL     1      -7.859   2.722   1.241  1.00  0.00           H  
HETATM  125  H61 UNL     1      -9.716   3.814   0.272  1.00  0.00           H  
HETATM  126  H62 UNL     1      -9.235   1.701  -1.182  1.00  0.00           H  
HETATM  127  H63 UNL     1     -11.120   1.601   1.710  1.00  0.00           H  
HETATM  128  H64 UNL     1     -10.857   3.277   2.161  1.00  0.00           H  
HETATM  129  H65 UNL     1     -13.141   3.102   1.529  1.00  0.00           H  
HETATM  130  H66 UNL     1     -12.229   4.236   0.523  1.00  0.00           H  
HETATM  131  H67 UNL     1     -12.296   2.599  -1.396  1.00  0.00           H  
HETATM  132  H68 UNL     1     -13.847   3.144  -0.773  1.00  0.00           H  
HETATM  133  H69 UNL     1     -13.854   0.870  -1.444  1.00  0.00           H  
HETATM  134  H70 UNL     1     -14.300   1.110   0.320  1.00  0.00           H  
HETATM  135  H71 UNL     1     -12.980  -0.947  -0.454  1.00  0.00           H  
HETATM  136  H72 UNL     1     -11.580   0.099  -0.596  1.00  0.00           H  
HETATM  137  H73 UNL     1     -12.424  -0.194   1.038  1.00  0.00           H  
HETATM  138  H74 UNL     1      -6.056   1.487   1.534  1.00  0.00           H  
HETATM  139  H75 UNL     1      -6.228   2.760   3.212  1.00  0.00           H  
HETATM  140  H76 UNL     1      -5.174   1.084   4.097  1.00  0.00           H  
HETATM  141  H77 UNL     1      -4.938  -0.949   4.522  1.00  0.00           H  
CONECT    1    2   65   66   67
CONECT    2    3   68   69
CONECT    3    4   70   71
CONECT    4    5   72   73
CONECT    5    6   74   75
CONECT    6    7    7   76
CONECT    7    8   77
CONECT    8    9   78   79
CONECT    9   10   10   80
CONECT   10   11   81
CONECT   11   12   82   83
CONECT   12   13   13   84
CONECT   13   14   85
CONECT   14   15   86   87
CONECT   15   16   88   89
CONECT   16   17   90   91
CONECT   17   18   92   93
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   94   95
CONECT   22   23   45   96
CONECT   23   24   97   98
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   99
CONECT   28   29
CONECT   29   30   63  100
CONECT   30   31   32  101
CONECT   31  102
CONECT   32   33   34  103
CONECT   33  104
CONECT   34   35   36  105
CONECT   35  106
CONECT   36   37   46  107
CONECT   37   38  108  109
CONECT   38   39   39  110
CONECT   39   40  111
CONECT   40   41  112  113
CONECT   41   42  114  115
CONECT   42   43  116  117
CONECT   43   44   44   45
CONECT   46   47   47   48
CONECT   48   49  118  119
CONECT   49   50   51  120
CONECT   50  121
CONECT   51   52   61  122
CONECT   52   53   53  123
CONECT   53   54  124
CONECT   54   55   56  125
CONECT   55  126
CONECT   56   57  127  128
CONECT   57   58  129  130
CONECT   58   59  131  132
CONECT   59   60  133  134
CONECT   60  135  136  137
CONECT   61   62   63  138
CONECT   62  139
CONECT   63   64  140
CONECT   64  141
END

HMDB0276779
     RDKit          3D
PI(18:3(6Z,9Z,12Z)/PGE2)
141142  0  0  0  0  0  0  0  0999 V2000
   16.8881   -0.6621    2.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3528    0.6052    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1256    1.0890    2.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9989    0.0887    2.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5577   -0.2600    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1020    0.9195    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9168    1.1026   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8215    0.1117   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6783    0.7319    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4935    0.9204   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2332    0.4910   -1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    1.6783   -2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442    1.8503   -2.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446    0.8340   -2.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    0.3857   -4.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794   -0.6077   -4.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9298   -0.2205   -4.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.0069   -2.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.6309   -1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.9232   -2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035    1.2942   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    0.2528   -0.1456 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3399    0.9096    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    0.4591    1.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8365    1.6846    2.2505 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.4098    2.5685    1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    2.7379    3.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126    1.0857    3.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292    0.3219    2.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4863   -1.0194    2.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4480   -1.1621    3.2260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.7075    1.0422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5251   -3.0816    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -1.2072   -0.3143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4492    0.1534   -0.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -1.8398   -1.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0746   -3.0953   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -2.6847   -2.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9174   -2.9427   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -4.1460   -2.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899   -3.8364   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -2.6366   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.1798   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -3.0023    0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.8673    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6708   -2.0155   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9945   -3.1137    0.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -0.8676    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.0944    1.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8998   -2.1656    2.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6357    0.1551    2.1511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7234    0.8654    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7220    2.1175    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9148    2.7203    0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0211    2.2048   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1074    2.5946    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3674    3.1287    0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9484    2.5036   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4427    1.1171   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5342    0.0137   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680    1.0125    2.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0021    2.1156    3.1919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3374    0.4001    3.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6183   -0.8038    3.8278 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3456   -1.5610    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9597   -0.7589    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7875   -0.5766    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1368    0.4301    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1457    1.3974    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3923    1.2562    3.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7759    2.0746    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1581    0.5286    2.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3537   -0.8322    2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4828   -0.7108    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8509   -1.0798    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8276    1.7429   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7002    2.0498   -0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1506   -0.7183    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6295   -0.3857   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8569    1.0533    1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6825    1.3827    0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4160   -0.2480   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762   -0.0395   -2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6178    2.4788   -2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734    2.7771   -3.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8084    0.0284   -2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311    1.4123   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001   -0.0944   -4.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1423    1.2821   -5.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -1.5658   -3.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1699   -0.9552   -5.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.7190   -4.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -0.9747   -4.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    1.6231   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.2351   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465   -0.0221   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1166    0.6713    1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465    2.0031    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    2.4415    4.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1883    0.9511    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837   -1.6936    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -2.0880    3.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -1.9365    1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841   -3.4722    1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -1.4483   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607    0.3077   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7807   -1.1256   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -3.8063   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107   -3.4924   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -2.1655   -3.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -2.2910   -3.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -4.9028   -2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400   -4.6573   -2.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -3.7321   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -4.6990   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -1.7570   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -2.9275   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9037    0.0137    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047   -0.7082   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3922   -1.4285    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4789   -2.9517    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0531   -0.1919    3.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6324    0.2813    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8595    2.7224    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7155    3.8145    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2354    1.7009   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1200    1.6009    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8569    3.2767    2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1411    3.1022    1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2294    4.2357    0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2961    2.5988   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8470    3.1445   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8535    0.8695   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3000    1.1096    0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9799   -0.9468   -0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5800    0.0990   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4239   -0.1940    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561    1.4873    1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2280    2.7600    3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1740    1.0835    4.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.9487    4.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(1R,6R,12Z,15R,18R,19S,20R,21R,22R,23S,24R)-3,18,20,21,22,23,24-Heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,16-trioxo-2,4,7-trioxa-3-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid	HMDB

Chemical Formula

C₄₇H₇₇O₁₆P

Average Molecular Weight

929.091

Monoisotopic Molecular Weight

928.494923397

IUPAC Name

[(1R,6R,12Z,15R,18R,19S,20R,21R,22R,23S,24R)-3,18,20,21,22,23,24-heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,16-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@@H]1COP(O)(=O)O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C\C=C/CCCC(=O)O1)C(=O)C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@H](O)[C@H]2O

InChI Identifier

InChI=1S/C47H77O16P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-23-27-40(51)60-32-35-33-61-64(58,59)63-47-45(56)43(54)37(30-29-34(48)25-21-6-4-2)39(50)31-38(49)36(42(53)44(55)46(47)57)26-22-19-20-24-28-41(52)62-35/h9-10,12-13,15-16,19,22,29-30,34-37,39,42-48,50,53-57H,3-8,11,14,17-18,20-21,23-28,31-33H2,1-2H3,(H,58,59)/b10-9-,13-12-,16-15-,22-19-,30-29+/t34-,35+,36-,37-,39+,42+,43+,44-,45+,46+,47+/m0/s1

InChI Key

XBVMAPFCARIVAP-HGWYJPIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Glycerophospholipid
Fatty acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

All cells and tissues (HMDB: HMDB0276779)

Cellular substructure

Organelle

Endoplasmic reticulum (PMID: 20519312)

Golgi apparatus membrane (PMID: 20519312)
Cell membrane (PMID: 20519312)

Source

Endogenous

Endogenous (HMDB: HMDB0276779)

Process

Naturally occurring process

Biological process

Cellular process

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	4.23	ALOGPS
logP	5.65	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	267.04 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	245.53 m³·mol⁻¹	ChemAxon
Polarizability	100.01 Å³	ChemAxon
Number of Rings	2	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]+	297.274	32859911
AllCCS	[M+H-H2O]+	297.612	32859911
AllCCS	[M+Na]+	296.814	32859911
AllCCS	[M+NH4]+	296.922	32859911
AllCCS	[M-H]-	290.528	32859911
AllCCS	[M+Na-2H]-	297.523	32859911
AllCCS	[M+HCOO]-	305.17	32859911
DeepCCS	[M+H]+	292.852	30932474
DeepCCS	[M-H]-	291.129	30932474
DeepCCS	[M-2H]-	325.16	30932474
DeepCCS	[M+Na]+	299.181	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 10V, Positive-QTOF	splash10-01t9-0000000009-80be1bf18e8707ca4d93	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 20V, Positive-QTOF	splash10-03di-2000000294-2f49b7e636f400dd5f99	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 40V, Positive-QTOF	splash10-0udi-2300009000-ec2ead28c1e7bbf12e3a	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 10V, Negative-QTOF	splash10-004i-0000000009-199581a34fe6f3e9f0b6	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 20V, Negative-QTOF	splash10-004i-0010002009-3995f3299cc244239f4f	2021-10-19	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PI(18:3(6Z,9Z,12Z)/PGE2) 40V, Negative-QTOF	splash10-014j-0000009040-da250e0e2cc50b3c30eb	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

156980131

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

Not Available

Showing metabocard for PI(18:3(6Z,9Z,12Z)/PGE2) (HMDB0276779)

MOL for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

3D MOL for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

3D SDF for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

3D-SDF for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

PDB for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

3D PDB for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

SMILES for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

INCHI for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

Structure for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

3D Structure for HMDB0276779 (PI(18:3(6Z,9Z,12Z)/PGE2))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra