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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-13 10:30:10 UTC

Update Date

2022-11-30 20:01:50 UTC

HMDB ID

HMDB0278652

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PIP(6 keto-PGF1alpha/16:2(9Z,12Z))

Description

PIP(6 keto-PGF1alpha/16:2(9Z,12Z)) is an oxidized phosphatidylinositol phosphate (PIP). As other PIPs, oxidized phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are 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. Phosphatidylinositol phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PIP(6 keto-PGF1alpha/16:2(9Z,12Z)), in particular, consists of one chain of 6-Keto-prostaglandin F1alpha at the C-1 position and one chain of 9Z,12Z-hexadecenoyl at the C-2 position. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositol phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.

Structure

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


  Mrv1652309132112302D          

 67 68  0  0  1  0            999 V2000
    2.1414    5.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266    5.3636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6410    6.1263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0792    6.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635    6.0630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4080    6.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    5.2612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1595    4.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    3.9742    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9935    4.5459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446    4.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    3.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337    2.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6144    2.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5511    1.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8071    0.9629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650    2.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274    3.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    3.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467    4.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    4.9385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5879    4.0733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2030    3.5814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    3.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916    4.0063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3400    4.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5723    3.5402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3327    2.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581    0.6926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6786    0.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5148   -0.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -0.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147   -0.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378   -0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.9969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492    0.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0475    2.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8120    1.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4769    2.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1400    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8744    2.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5448    1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3390    1.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0095    1.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8208    1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0245    2.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8187    2.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0224    3.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4319    4.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6357    4.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4299    5.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5006    4.6766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2644    5.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    6.2223    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    6.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6067    7.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438    7.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4373    3.8540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3482    3.3693    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  1  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  0  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
 23 25  1  0  0  0  0
 26 25  1  6  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 14 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 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
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  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
  7 60  1  0  0  0  0
 60 61  1  6  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 62 65  2  0  0  0  0
 60 66  1  0  0  0  0
 32 66  1  0  0  0  0
 66 67  1  6  0  0  0
M  END

HMDB0278652
     RDKit          3D
PIP(6 keto-PGF1alpha/16:2(9Z,12Z))
145146  0  0  0  0  0  0  0  0999 V2000
   12.2988    1.1629    3.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0510    0.6349    2.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014    1.7896    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1201    1.2320    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8175    1.2499   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740    1.8366   -1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6764    2.5999   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4206    2.2502   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112    1.0475   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2470    0.2479   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5957   -1.0195   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576   -0.7881   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3563    0.0400   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2822    0.1906   -1.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211    0.9981   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449    0.3145   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.5693    0.9153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5298   -0.6029   -0.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -1.3112    0.6429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0763   -2.8106    0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562   -3.1350   -0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -3.8006   -1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704   -4.6614   -2.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084   -3.5585   -2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -4.5604   -2.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -3.7943   -1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -4.5894   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502   -3.8187   -2.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -3.3720   -3.8943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183   -3.6148   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649   -2.1633   -2.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2048   -1.8321   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2768   -2.7230   -1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6617   -2.1011    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2133   -1.4762    1.2372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7777   -2.2758    2.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2332   -0.0942    1.6186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4165    0.5544    0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965    0.7236    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6926    1.3791    0.6551 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.8333    1.5343    1.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2248    2.6619    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7487    3.6822    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7640    4.1290    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9768    4.7643    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6236    5.9936    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1641    0.8641    1.6695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3822    1.7777    2.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149    0.5175    1.6310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4172   -0.7778    1.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -0.9460    3.5008 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9875    0.3689    3.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -2.1500    3.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -1.2517    4.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    1.0585    0.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8862    1.8239    0.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    1.4198    0.7385 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.3868    1.3436   -0.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    2.6709    1.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    0.0162    1.5849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -1.0124    0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127    0.1113   -0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8616    0.5344   -1.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.0306   -1.5595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1027    1.1632   -2.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304   -1.2169   -2.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7963   -0.7793   -3.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6664    0.7269    4.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3778    2.2590    3.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2086    0.9236    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9899    0.1548    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4454   -0.1360    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1562    2.4081    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5554    2.4282    1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0829    0.7085    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5412    0.7334   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1087    2.5597   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1442    1.1048   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9435    3.5870   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7502    2.9236   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8954    1.3637   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3855    0.4318   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5634    0.8990    0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1043   -0.0121    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3425   -1.6553   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2271   -1.5492    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -1.7818   -1.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010   -0.2742   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -0.4577    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309132112302D          

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M  END
> <DATABASE_ID>
HMDB0278652

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]2CC(=O)CCCCC(=O)OC[C@H](COP(O)(=O)O[C@@H]([C@H](O)[C@@H](O)[C@@H]2O)[C@H](OP(O)(O)=O)[C@@H]1O)OC(=O)CCCCCCC\C=C/C\C=C/CCC

> <INCHI_IDENTIFIER>
InChI=1S/C45H78O20P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-24-39(51)63-33-29-61-38(50)23-20-19-22-32(47)27-35-37(49)28-36(48)34(26-25-31(46)21-17-6-4-2)41(53)44(64-66(56,57)58)45(43(55)42(54)40(35)52)65-67(59,60)62-30-33/h7-8,10-11,25-26,31,33-37,40-46,48-49,52-55H,3-6,9,12-24,27-30H2,1-2H3,(H,59,60)(H2,56,57,58)/b8-7-,11-10-,26-25+/t31-,33+,34-,35-,36+,37-,40+,41+,42-,43+,44+,45-/m0/s1

> <INCHI_KEY>
RRGFGXPNSQMVHB-QFDAYXBPSA-N

> <FORMULA>
C45H78O20P2

> <MOLECULAR_WEIGHT>
1001.047

> <EXACT_MASS>
1000.456168908

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
145

> <JCHEM_AVERAGE_POLARIZABILITY>
102.71487677045806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1S,6R,16S,17S,19R,20S,21R,22R,23R,24S,25R)-6-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3,17,19,21,23,24,25-heptahydroxy-20-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,9,14-trioxo-2,4,8-trioxa-3lambda5-phosphabicyclo[14.6.3]pentacosan-22-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
3.4551206503333334

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.8950501542898976

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.956217472950188

> <JCHEM_PKA_STRONGEST_BASIC>
-2.919011464900932

> <JCHEM_POLAR_SURFACE_AREA>
333.8

> <JCHEM_REFRACTIVITY>
246.6962000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,6R,16S,17S,19R,20S,21R,22R,23R,24S,25R)-6-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3,17,19,21,23,24,25-heptahydroxy-20-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,9,14-trioxo-2,4,8-trioxa-3lambda5-phosphabicyclo[14.6.3]pentacosan-22-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0278652
     RDKit          3D
PIP(6 keto-PGF1alpha/16:2(9Z,12Z))
145146  0  0  0  0  0  0  0  0999 V2000
   12.2988    1.1629    3.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0510    0.6349    2.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014    1.7896    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1201    1.2320    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8175    1.2499   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740    1.8366   -1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6764    2.5999   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4206    2.2502   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112    1.0475   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5957   -1.0195   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3704   -4.6614   -2.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2346   -4.5604   -2.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -3.7943   -1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -4.5894   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7183   -3.6148   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649   -2.1633   -2.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2048   -1.8321   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2768   -2.7230   -1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
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 62140  1  1
 63141  1  0
 64142  1  1
 65143  1  0
 66144  1  1
 67145  1  0
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       3.997  10.512   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.476  10.012   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.063  11.436   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.015  12.681   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.599  11.318   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.495  12.970   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.961   9.821   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.898   8.954   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       5.780   7.418   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       7.455   8.486   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.550   7.506   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.050   6.548   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.343   4.868   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.614   3.998   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.495   2.463   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.107   1.797   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.836   2.667   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.332   3.484   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.858   1.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.176   2.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.295   4.408   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.024   5.278   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.731   6.958   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.363   6.509   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.461   7.828   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.990   9.219   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.097   7.604   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.379   6.685   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.368   6.733   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.531   7.478   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.501   8.840   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.802   6.608   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.354   4.785   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.349   2.954   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.655   1.293   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.000   0.066   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.144   0.431   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.961  -0.714   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.652  -0.405   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.521  -1.701   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.057  -1.598   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.315   3.728   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      11.853   3.103   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      12.225   1.569   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      13.155   4.125   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.582   3.339   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.823   4.328   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      17.061   3.340   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      18.432   4.128   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      19.684   3.157   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      21.166   3.728   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      22.418   2.742   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.932   3.167   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      24.312   4.660   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      25.795   5.077   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      26.175   6.569   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      25.073   7.644   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      25.453   9.137   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.936   9.553   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.535   8.730   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       7.960  10.105   0.000  0.00  0.00           O+0
HETATM   62  P   UNK     0       8.922  11.615   0.000  0.00  0.00           P+0
HETATM   63  O   UNK     0      10.558  11.619   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       8.599  13.216   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       9.415  13.221   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       6.416   7.194   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       8.117   6.289   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   60                                                  
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   42                                                  
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   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   66                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   14   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58                                                            
CONECT   60    7   61   66                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   64   65                                             
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65   62                                                            
CONECT   66   60   32   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  136    0
END

COMPND    HMDB0278652
HETATM    1  C1  UNL     1      12.299   1.163   3.660  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.051   0.635   2.476  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.401   1.790   1.489  1.00  0.00           C  
HETATM    4  C4  UNL     1      14.120   1.232   0.373  1.00  0.00           C  
HETATM    5  C5  UNL     1      13.818   1.250  -0.875  1.00  0.00           C  
HETATM    6  C6  UNL     1      12.674   1.837  -1.527  1.00  0.00           C  
HETATM    7  C7  UNL     1      11.676   2.600  -0.826  1.00  0.00           C  
HETATM    8  C8  UNL     1      10.421   2.250  -0.717  1.00  0.00           C  
HETATM    9  C9  UNL     1       9.811   1.048  -1.273  1.00  0.00           C  
HETATM   10  C10 UNL     1       9.247   0.248  -0.104  1.00  0.00           C  
HETATM   11  C11 UNL     1       8.596  -1.019  -0.566  1.00  0.00           C  
HETATM   12  C12 UNL     1       7.458  -0.788  -1.504  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.356   0.040  -0.870  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.282   0.191  -1.924  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.121   0.998  -1.404  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.545   0.315  -0.231  1.00  0.00           C  
HETATM   17  O1  UNL     1       3.977   0.569   0.915  1.00  0.00           O  
HETATM   18  O2  UNL     1       2.530  -0.603  -0.421  1.00  0.00           O  
HETATM   19  C17 UNL     1       1.910  -1.311   0.643  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.076  -2.811   0.462  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.956  -3.135  -0.579  1.00  0.00           O  
HETATM   22  C19 UNL     1       2.591  -3.801  -1.740  1.00  0.00           C  
HETATM   23  O4  UNL     1       3.370  -4.661  -2.266  1.00  0.00           O  
HETATM   24  C20 UNL     1       1.308  -3.558  -2.421  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.235  -4.560  -2.017  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.044  -3.794  -1.848  1.00  0.00           C  
HETATM   27  C23 UNL     1      -2.288  -4.589  -2.064  1.00  0.00           C  
HETATM   28  C24 UNL     1      -3.350  -3.819  -2.811  1.00  0.00           C  
HETATM   29  O5  UNL     1      -3.015  -3.372  -3.894  1.00  0.00           O  
HETATM   30  C25 UNL     1      -4.718  -3.615  -2.266  1.00  0.00           C  
HETATM   31  C26 UNL     1      -5.165  -2.163  -2.375  1.00  0.00           C  
HETATM   32  C27 UNL     1      -6.205  -1.832  -1.294  1.00  0.00           C  
HETATM   33  O6  UNL     1      -7.277  -2.723  -1.582  1.00  0.00           O  
HETATM   34  C28 UNL     1      -5.662  -2.101   0.057  1.00  0.00           C  
HETATM   35  C29 UNL     1      -6.213  -1.476   1.237  1.00  0.00           C  
HETATM   36  O7  UNL     1      -5.778  -2.276   2.350  1.00  0.00           O  
HETATM   37  C30 UNL     1      -6.233  -0.094   1.619  1.00  0.00           C  
HETATM   38  C31 UNL     1      -7.417   0.554   0.919  1.00  0.00           C  
HETATM   39  C32 UNL     1      -8.596   0.724   1.442  1.00  0.00           C  
HETATM   40  C33 UNL     1      -9.693   1.379   0.655  1.00  0.00           C  
HETATM   41  O8  UNL     1     -10.833   1.534   1.397  1.00  0.00           O  
HETATM   42  C34 UNL     1      -9.225   2.662   0.025  1.00  0.00           C  
HETATM   43  C35 UNL     1      -8.749   3.682   1.004  1.00  0.00           C  
HETATM   44  C36 UNL     1      -9.764   4.129   2.000  1.00  0.00           C  
HETATM   45  C37 UNL     1     -10.977   4.764   1.380  1.00  0.00           C  
HETATM   46  C38 UNL     1     -10.624   5.994   0.569  1.00  0.00           C  
HETATM   47  C39 UNL     1      -5.164   0.864   1.670  1.00  0.00           C  
HETATM   48  O9  UNL     1      -5.382   1.778   2.750  1.00  0.00           O  
HETATM   49  C40 UNL     1      -3.715   0.517   1.631  1.00  0.00           C  
HETATM   50  O10 UNL     1      -3.417  -0.778   1.985  1.00  0.00           O  
HETATM   51  P1  UNL     1      -2.686  -0.946   3.501  1.00  0.00           P  
HETATM   52  O11 UNL     1      -1.988   0.369   3.829  1.00  0.00           O  
HETATM   53  O12 UNL     1      -1.506  -2.150   3.480  1.00  0.00           O  
HETATM   54  O13 UNL     1      -3.832  -1.252   4.706  1.00  0.00           O  
HETATM   55  C41 UNL     1      -2.967   1.058   0.428  1.00  0.00           C  
HETATM   56  O14 UNL     1      -1.886   1.824   0.718  1.00  0.00           O  
HETATM   57  P2  UNL     1      -0.363   1.420   0.739  1.00  0.00           P  
HETATM   58  O15 UNL     1       0.387   1.344  -0.585  1.00  0.00           O  
HETATM   59  O16 UNL     1       0.491   2.671   1.580  1.00  0.00           O  
HETATM   60  O17 UNL     1       0.105   0.016   1.585  1.00  0.00           O  
HETATM   61  C42 UNL     1       0.431  -1.012   0.722  1.00  0.00           C  
HETATM   62  C43 UNL     1      -2.813   0.111  -0.713  1.00  0.00           C  
HETATM   63  O18 UNL     1      -1.862   0.534  -1.639  1.00  0.00           O  
HETATM   64  C44 UNL     1      -4.069  -0.031  -1.560  1.00  0.00           C  
HETATM   65  O19 UNL     1      -4.103   1.163  -2.331  1.00  0.00           O  
HETATM   66  C45 UNL     1      -4.030  -1.217  -2.455  1.00  0.00           C  
HETATM   67  O20 UNL     1      -3.796  -0.779  -3.761  1.00  0.00           O  
HETATM   68  H1  UNL     1      12.666   0.727   4.616  1.00  0.00           H  
HETATM   69  H2  UNL     1      12.378   2.259   3.661  1.00  0.00           H  
HETATM   70  H3  UNL     1      11.209   0.924   3.525  1.00  0.00           H  
HETATM   71  H4  UNL     1      13.990   0.155   2.814  1.00  0.00           H  
HETATM   72  H5  UNL     1      12.445  -0.136   1.957  1.00  0.00           H  
HETATM   73  H6  UNL     1      14.156   2.408   2.090  1.00  0.00           H  
HETATM   74  H7  UNL     1      12.555   2.428   1.364  1.00  0.00           H  
HETATM   75  H8  UNL     1      15.083   0.708   0.645  1.00  0.00           H  
HETATM   76  H9  UNL     1      14.541   0.733  -1.611  1.00  0.00           H  
HETATM   77  H10 UNL     1      13.109   2.560  -2.336  1.00  0.00           H  
HETATM   78  H11 UNL     1      12.144   1.105  -2.211  1.00  0.00           H  
HETATM   79  H12 UNL     1      11.944   3.587  -0.371  1.00  0.00           H  
HETATM   80  H13 UNL     1       9.750   2.924  -0.152  1.00  0.00           H  
HETATM   81  H14 UNL     1       8.895   1.364  -1.859  1.00  0.00           H  
HETATM   82  H15 UNL     1      10.386   0.432  -1.947  1.00  0.00           H  
HETATM   83  H16 UNL     1       8.563   0.899   0.448  1.00  0.00           H  
HETATM   84  H17 UNL     1      10.104  -0.012   0.551  1.00  0.00           H  
HETATM   85  H18 UNL     1       9.342  -1.655  -1.064  1.00  0.00           H  
HETATM   86  H19 UNL     1       8.227  -1.549   0.340  1.00  0.00           H  
HETATM   87  H20 UNL     1       6.994  -1.782  -1.733  1.00  0.00           H  
HETATM   88  H21 UNL     1       7.801  -0.274  -2.426  1.00  0.00           H  
HETATM   89  H22 UNL     1       5.951  -0.458   0.016  1.00  0.00           H  
HETATM   90  H23 UNL     1       6.731   1.036  -0.561  1.00  0.00           H  
HETATM   91  H24 UNL     1       5.689   0.678  -2.833  1.00  0.00           H  
HETATM   92  H25 UNL     1       4.893  -0.832  -2.155  1.00  0.00           H  
HETATM   93  H26 UNL     1       3.335   1.108  -2.169  1.00  0.00           H  
HETATM   94  H27 UNL     1       4.533   1.998  -1.132  1.00  0.00           H  
HETATM   95  H28 UNL     1       2.376  -0.966   1.585  1.00  0.00           H  
HETATM   96  H29 UNL     1       2.499  -3.208   1.407  1.00  0.00           H  
HETATM   97  H30 UNL     1       1.077  -3.312   0.341  1.00  0.00           H  
HETATM   98  H31 UNL     1       1.393  -3.567  -3.521  1.00  0.00           H  
HETATM   99  H32 UNL     1       0.996  -2.516  -2.149  1.00  0.00           H  
HETATM  100  H33 UNL     1       0.524  -5.137  -1.128  1.00  0.00           H  
HETATM  101  H34 UNL     1       0.096  -5.302  -2.849  1.00  0.00           H  
HETATM  102  H35 UNL     1      -1.019  -3.247  -0.884  1.00  0.00           H  
HETATM  103  H36 UNL     1      -1.033  -2.984  -2.635  1.00  0.00           H  
HETATM  104  H37 UNL     1      -2.703  -4.864  -1.053  1.00  0.00           H  
HETATM  105  H38 UNL     1      -2.086  -5.524  -2.589  1.00  0.00           H  
HETATM  106  H39 UNL     1      -4.723  -4.009  -1.253  1.00  0.00           H  
HETATM  107  H40 UNL     1      -5.396  -4.285  -2.871  1.00  0.00           H  
HETATM  108  H41 UNL     1      -5.735  -2.101  -3.329  1.00  0.00           H  
HETATM  109  H42 UNL     1      -6.620  -0.860  -1.510  1.00  0.00           H  
HETATM  110  H43 UNL     1      -7.786  -2.421  -2.372  1.00  0.00           H  
HETATM  111  H44 UNL     1      -5.876  -3.221   0.217  1.00  0.00           H  
HETATM  112  H45 UNL     1      -4.560  -2.156  -0.047  1.00  0.00           H  
HETATM  113  H46 UNL     1      -7.314  -1.802   1.222  1.00  0.00           H  
HETATM  114  H47 UNL     1      -6.427  -2.108   3.096  1.00  0.00           H  
HETATM  115  H48 UNL     1      -6.650  -0.149   2.695  1.00  0.00           H  
HETATM  116  H49 UNL     1      -7.275   0.916  -0.100  1.00  0.00           H  
HETATM  117  H50 UNL     1      -8.754   0.371   2.469  1.00  0.00           H  
HETATM  118  H51 UNL     1      -9.904   0.672  -0.190  1.00  0.00           H  
HETATM  119  H52 UNL     1     -11.054   0.719   1.875  1.00  0.00           H  
HETATM  120  H53 UNL     1     -10.123   3.101  -0.494  1.00  0.00           H  
HETATM  121  H54 UNL     1      -8.480   2.498  -0.776  1.00  0.00           H  
HETATM  122  H55 UNL     1      -7.861   3.306   1.553  1.00  0.00           H  
HETATM  123  H56 UNL     1      -8.437   4.582   0.416  1.00  0.00           H  
HETATM  124  H57 UNL     1     -10.094   3.336   2.683  1.00  0.00           H  
HETATM  125  H58 UNL     1      -9.278   4.916   2.629  1.00  0.00           H  
HETATM  126  H59 UNL     1     -11.586   4.093   0.765  1.00  0.00           H  
HETATM  127  H60 UNL     1     -11.625   5.122   2.222  1.00  0.00           H  
HETATM  128  H61 UNL     1     -11.456   6.749   0.641  1.00  0.00           H  
HETATM  129  H62 UNL     1      -9.721   6.499   0.914  1.00  0.00           H  
HETATM  130  H63 UNL     1     -10.571   5.699  -0.498  1.00  0.00           H  
HETATM  131  H64 UNL     1      -5.276   1.602   0.816  1.00  0.00           H  
HETATM  132  H65 UNL     1      -6.070   1.389   3.348  1.00  0.00           H  
HETATM  133  H66 UNL     1      -3.230   1.104   2.483  1.00  0.00           H  
HETATM  134  H67 UNL     1      -1.971  -3.028   3.513  1.00  0.00           H  
HETATM  135  H68 UNL     1      -4.077  -0.370   5.135  1.00  0.00           H  
HETATM  136  H69 UNL     1      -3.691   1.846   0.021  1.00  0.00           H  
HETATM  137  H70 UNL     1       0.367   3.532   1.068  1.00  0.00           H  
HETATM  138  H71 UNL     1      -0.052  -1.934   1.167  1.00  0.00           H  
HETATM  139  H72 UNL     1       0.053  -0.866  -0.316  1.00  0.00           H  
HETATM  140  H73 UNL     1      -2.560  -0.899  -0.344  1.00  0.00           H  
HETATM  141  H74 UNL     1      -1.502  -0.270  -2.096  1.00  0.00           H  
HETATM  142  H75 UNL     1      -4.920   0.048  -0.907  1.00  0.00           H  
HETATM  143  H76 UNL     1      -3.392   1.048  -3.002  1.00  0.00           H  
HETATM  144  H77 UNL     1      -3.096  -1.787  -2.180  1.00  0.00           H  
HETATM  145  H78 UNL     1      -4.653  -0.576  -4.206  1.00  0.00           H  
CONECT    1    2   68   69   70
CONECT    2    3   71   72
CONECT    3    4   73   74
CONECT    4    5    5   75
CONECT    5    6   76
CONECT    6    7   77   78
CONECT    7    8    8   79
CONECT    8    9   80
CONECT    9   10   81   82
CONECT   10   11   83   84
CONECT   11   12   85   86
CONECT   12   13   87   88
CONECT   13   14   89   90
CONECT   14   15   91   92
CONECT   15   16   93   94
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   61   95
CONECT   20   21   96   97
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   98   99
CONECT   25   26  100  101
CONECT   26   27  102  103
CONECT   27   28  104  105
CONECT   28   29   29   30
CONECT   30   31  106  107
CONECT   31   32   66  108
CONECT   32   33   34  109
CONECT   33  110
CONECT   34   35  111  112
CONECT   35   36   37  113
CONECT   36  114
CONECT   37   38   47  115
CONECT   38   39   39  116
CONECT   39   40  117
CONECT   40   41   42  118
CONECT   41  119
CONECT   42   43  120  121
CONECT   43   44  122  123
CONECT   44   45  124  125
CONECT   45   46  126  127
CONECT   46  128  129  130
CONECT   47   48   49  131
CONECT   48  132
CONECT   49   50   55  133
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53  134
CONECT   54  135
CONECT   55   56   62  136
CONECT   56   57
CONECT   57   58   58   59   60
CONECT   59  137
CONECT   60   61
CONECT   61  138  139
CONECT   62   63   64  140
CONECT   63  141
CONECT   64   65   66  142
CONECT   65  143
CONECT   66   67  144
CONECT   67  145
END

HMDB0278652
     RDKit          3D
PIP(6 keto-PGF1alpha/16:2(9Z,12Z))
145146  0  0  0  0  0  0  0  0999 V2000
   12.2988    1.1629    3.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0510    0.6349    2.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014    1.7896    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1201    1.2320    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8175    1.2499   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740    1.8366   -1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6764    2.5999   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4206    2.2502   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112    1.0475   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2470    0.2479   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5957   -1.0195   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576   -0.7881   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3563    0.0400   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2822    0.1906   -1.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211    0.9981   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449    0.3145   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.5693    0.9153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5298   -0.6029   -0.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -1.3112    0.6429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0763   -2.8106    0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562   -3.1350   -0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -3.8006   -1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704   -4.6614   -2.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084   -3.5585   -2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -4.5604   -2.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -3.7943   -1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -4.5894   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502   -3.8187   -2.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -3.3720   -3.8943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183   -3.6148   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649   -2.1633   -2.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2048   -1.8321   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2768   -2.7230   -1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6617   -2.1011    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2133   -1.4762    1.2372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7777   -2.2758    2.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2332   -0.0942    1.6186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4165    0.5544    0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965    0.7236    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6926    1.3791    0.6551 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.8333    1.5343    1.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2248    2.6619    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7487    3.6822    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7640    4.1290    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9768    4.7643    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6236    5.9936    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1641    0.8641    1.6695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3822    1.7777    2.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149    0.5175    1.6310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4172   -0.7778    1.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -0.9460    3.5008 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9875    0.3689    3.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -2.1500    3.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -1.2517    4.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    1.0585    0.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8862    1.8239    0.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    1.4198    0.7385 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.3868    1.3436   -0.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    2.6709    1.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    0.0162    1.5849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -1.0124    0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127    0.1113   -0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8616    0.5344   -1.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.0306   -1.5595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1027    1.1632   -2.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304   -1.2169   -2.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7963   -0.7793   -3.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6664    0.7269    4.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3778    2.2590    3.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2086    0.9236    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9899    0.1548    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4454   -0.1360    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1562    2.4081    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5554    2.4282    1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0829    0.7085    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5412    0.7334   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1087    2.5597   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1442    1.1048   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9435    3.5870   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7502    2.9236   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8954    1.3637   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3855    0.4318   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5634    0.8990    0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1043   -0.0121    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3425   -1.6553   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2271   -1.5492    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -1.7818   -1.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010   -0.2742   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4990   -3.2078    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3931   -3.5670   -3.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0857   -5.5236   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225   -4.0088   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963   -4.2849   -2.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7352   -2.1009   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6196   -0.8596   -1.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7856   -2.4210   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8760   -3.2214    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4800    2.4981   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8613    3.3064    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2778    4.9162    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6246    5.1221    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4559    6.7494    0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7209    6.4990    0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5709    5.6990   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2755    1.6022    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0700    1.3886    3.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2299    1.1039    2.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -3.0276    3.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773   -0.3703    5.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6910    1.8456    0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3673    3.5321    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0519   -1.9344    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -0.8659   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598   -0.8993   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -0.2700   -2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9200    0.0478   -0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    1.0484   -3.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0965   -1.7868   -2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6530   -0.5759   -4.2056 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
{[(1S,6R,16S,17S,19R,20S,21R,22R,23R,24S,25R)-6-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3,17,19,21,23,24,25-heptahydroxy-20-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,9,14-trioxo-2,4,8-trioxa-3-phosphabicyclo[14.6.3]pentacosan-22-yl]oxy}phosphonate	HMDB

Chemical Formula

C₄₅H₇₈O₂₀P₂

Average Molecular Weight

1001.047

Monoisotopic Molecular Weight

1000.456168908

IUPAC Name

{[(1S,6R,16S,17S,19R,20S,21R,22R,23R,24S,25R)-6-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3,17,19,21,23,24,25-heptahydroxy-20-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,9,14-trioxo-2,4,8-trioxa-3lambda5-phosphabicyclo[14.6.3]pentacosan-22-yl]oxy}phosphonic acid

Traditional Name

[(1S,6R,16S,17S,19R,20S,21R,22R,23R,24S,25R)-6-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3,17,19,21,23,24,25-heptahydroxy-20-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,9,14-trioxo-2,4,8-trioxa-3lambda5-phosphabicyclo[14.6.3]pentacosan-22-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]2CC(=O)CCCCC(=O)OC[C@H](COP(O)(=O)O[C@@H]([C@H](O)[C@@H](O)[C@@H]2O)[C@H](OP(O)(O)=O)[C@@H]1O)OC(=O)CCCCCCC\C=C/C\C=C/CCC

InChI Identifier

InChI=1S/C45H78O20P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-24-39(51)63-33-29-61-38(50)23-20-19-22-32(47)27-35-37(49)28-36(48)34(26-25-31(46)21-17-6-4-2)41(53)44(64-66(56,57)58)45(43(55)42(54)40(35)52)65-67(59,60)62-30-33/h7-8,10-11,25-26,31,33-37,40-46,48-49,52-55H,3-6,9,12-24,27-30H2,1-2H3,(H,59,60)(H2,56,57,58)/b8-7-,11-10-,26-25+/t31-,33+,34-,35-,36+,37-,40+,41+,42-,43+,44+,45-/m0/s1

InChI Key

RRGFGXPNSQMVHB-QFDAYXBPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophospholipids. These are derivatives of glycerophosphoric acid that contains at least one O-acyl, or O-alkyl, or O-(1-alkenyl) group attached to the glycerol residue.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Not Available

Direct Parent

Glycerophospholipids

Alternative Parents

Substituents

Glycerophospholipid
Monoalkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Cyclic ketone
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: HMDB0278652)

Cellular substructure

Organelle

Endoplasmic reticulum (PMID: 20519312)

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

Source

Endogenous

Endogenous (HMDB: HMDB0278652)

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	2.15	ALOGPS
logP	3.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	0.96	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	333.8 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	246.7 m³·mol⁻¹	ChemAxon
Polarizability	102.71 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]+	303.012	32859911
AllCCS	[M+H-H2O]+	303.465	32859911
AllCCS	[M+Na]+	302.417	32859911
AllCCS	[M+NH4]+	302.555	32859911
AllCCS	[M-H]-	312.004	32859911
AllCCS	[M+Na-2H]-	318.6	32859911
AllCCS	[M+HCOO]-	325.807	32859911
DeepCCS	[M+H]+	244.669	30932474
DeepCCS	[M-H]-	243.008	30932474
DeepCCS	[M-2H]-	277.039	30932474
DeepCCS	[M+Na]+	250.817	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

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

156982004

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 PIP(6 keto-PGF1alpha/16:2(9Z,12Z)) (HMDB0278652)

MOL for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

3D MOL for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

3D SDF for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

3D-SDF for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

PDB for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

3D PDB for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

SMILES for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

INCHI for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

Structure for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

3D Structure for HMDB0278652 (PIP(6 keto-PGF1alpha/16:2(9Z,12Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices