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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (80) Show 80 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-12 02:02:35 UTC

Update Date

2022-11-30 19:03:44 UTC

HMDB ID

HMDB0009952

Secondary Accession Numbers

HMDB09952

Metabolite Identification

Common Name

PIP(18:0/18:3(6Z,9Z,12Z))

Description

PIP(18:0/18:3(6Z,9Z,12Z)) is a phosphatidylinositol phosphate. 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. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(18:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the g-linolenic acid moiety is derived from animal fats. 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. Phosphatidylinositols 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


  Mrv0541 02241200132D          

 64 64  0  0  1  0            999 V2000
   16.9311   -4.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5001   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0690   -4.9687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6379   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2068   -4.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6733   -5.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5667   -5.5900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3622   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3622   -3.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1043   -5.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1043   -6.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7933   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8221   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5649   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3077   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0505   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0793   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3364   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5936   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8508   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1080   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3651   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6224   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796   -4.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3940   -4.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5354   -5.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8616   -5.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1877   -5.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6511   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083   -4.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5139   -5.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8400   -5.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6411   -5.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0552   -5.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6373   -5.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1655   -5.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935   -5.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9079   -5.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6223   -5.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3368   -5.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9228   -5.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4653   -5.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3725   -5.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1837   -5.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1537   -4.5487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.8375   -3.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5376   -3.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5443   -3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8299   -4.6078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.1393   -4.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5529   -4.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2242   -3.7769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4320   -4.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1529   -3.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1128   -3.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1442   -2.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8799   -4.5801    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.2685   -5.2532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4913   -3.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7163   -4.2509    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.0069   -3.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1258   -5.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7287   -4.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  3  6  1  6  0  0  0
  3  7  1  1  0  0  0
  9  8  2  0  0  0  0
  1  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10 11  2  0  0  0  0
 12  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 12 16  1  0  0  0  0
 17 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 10  1  0  0  0  0
 29 28  1  0  0  0  0
 27 28  1  0  0  0  0
 30 26  1  0  0  0  0
 31 30  1  0  0  0  0
 32 29  1  0  0  0  0
 33 32  1  0  0  0  0
 35 34  1  0  0  0  0
 37 36  1  0  0  0  0
 39 38  1  0  0  0  0
 40 39  1  0  0  0  0
 41 40  1  0  0  0  0
 42 41  1  0  0  0  0
 43 42  1  0  0  0  0
 37 43  2  0  0  0  0
 44 36  1  0  0  0  0
 35 44  2  0  0  0  0
 45 34  1  0  0  0  0
 33 45  2  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
 50 51  1  1  0  0  0
 46 51  1  1  0  0  0
 52 46  1  0  0  0  0
 53 47  1  0  0  0  0
 54 50  1  0  0  0  0
 55 49  1  0  0  0  0
 48 56  1  0  0  0  0
 51 57  1  0  0  0  0
  5 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  2  0  0  0  0
 58 52  1  0  0  0  0
 61 54  1  0  0  0  0
 61 62  2  0  0  0  0
 61 63  1  0  0  0  0
 61 64  1  0  0  0  0
M  END

HMDB0009952
     RDKit          3D
PIP(18:0/18:3(6Z,9Z,12Z))
145145  0  0  0  0  0  0  0  0999 V2000
    2.5413    1.0087    9.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.1451    8.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    2.0379    9.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156    0.8189    8.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043    0.5594    9.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.7275    8.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223   -0.9093    8.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.0922    7.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    0.4783    6.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066    0.2246    5.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -0.6105    5.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -1.7755    4.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0113   -2.2353    3.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -1.8420    3.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6802   -1.5101    2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0222   -0.2106    1.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    0.1912    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684   -0.6722   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -1.7049    0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3532   -0.2823   -1.5175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755   -1.0576   -2.0520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0507   -0.0956   -1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    0.1518   -0.3844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    0.9432    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868    1.4922   -0.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229    1.1104    1.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867    2.3742    2.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293    2.7606    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3320    3.3067    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090    4.7685    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7268    5.1469   -1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    4.4908   -1.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    5.1640   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    4.7045   -0.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    4.4841   -2.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    4.1031   -1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314    3.7193   -2.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016    2.4577   -3.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463    1.9748   -4.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9301    1.7579   -4.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9950    0.7996   -2.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6074   -0.6132   -3.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725   -1.3688   -3.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571   -2.1392   -3.8830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -2.5182   -5.5130 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.4326   -1.7559   -6.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021   -4.1747   -5.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332   -2.2079   -6.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854   -3.0801   -5.8405 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8580   -3.8267   -6.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2119   -3.6407   -8.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2741   -3.3398   -7.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570   -4.1997   -8.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936   -3.4340   -5.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8716   -4.5784   -5.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.3333   -4.6119 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8164   -3.0418   -3.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866   -4.2450   -2.2949 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5156   -5.1616   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -5.2024   -2.9137 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857   -3.4050   -0.9412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3245   -4.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149   -1.8288   -3.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1407    0.7246    8.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    1.3951    9.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082    0.1548    9.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398    2.1512    7.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    3.0873    8.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222    2.0070   10.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717    2.9744    9.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116   -0.0665    8.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6349    0.9546    7.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192    1.4232    9.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332    0.3785   10.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104   -1.5641    9.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572   -1.9574    7.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    0.9997    8.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236   -0.3641    8.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4629    1.1736    6.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4489    0.7261    4.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -0.8568    6.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225    0.0474    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855   -2.3283    4.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516   -3.2049    3.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197   -2.7847    3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7879   -1.0874    4.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7680   -1.4599    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2840   -2.3467    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9932   -0.1615    2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670    0.6301    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8961    0.0463   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241200132D          

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M  END
> <DATABASE_ID>
HMDB0009952

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C45H82O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h12,14,18,20,24,26,37,40-45,48-51H,3-11,13,15-17,19,21-23,25,27-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b14-12-,20-18-,26-24-/t37-,40?,41?,42?,43?,44-,45+/m1/s1

> <INCHI_KEY>
KDKGDGWOVUFBBB-QEXOWQMYSA-N

> <FORMULA>
C45H82O16P2

> <MOLECULAR_WEIGHT>
941.0705

> <EXACT_MASS>
940.5078096

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
104.20513466253665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
6.55

> <JCHEM_LOGP>
9.562999548666665

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.9166523982543264

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0756803498311691

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6477611462617663

> <JCHEM_POLAR_SURFACE_AREA>
256.03999999999996

> <JCHEM_REFRACTIVITY>
243.19450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0009952
     RDKit          3D
PIP(18:0/18:3(6Z,9Z,12Z))
145145  0  0  0  0  0  0  0  0999 V2000
    2.5413    1.0087    9.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.1451    8.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    2.0379    9.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156    0.8189    8.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043    0.5594    9.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.7275    8.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223   -0.9093    8.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.0922    7.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    0.4783    6.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066    0.2246    5.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -0.6105    5.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -1.7755    4.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0113   -2.2353    3.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -1.8420    3.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0507   -0.0956   -1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      31.605  -9.275   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      32.667  -8.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.729  -9.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.791  -8.662   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      35.853  -9.275   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      32.990 -10.413   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      34.658 -10.435   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      30.543  -8.662   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      30.543  -7.435   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      31.928 -11.026   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      31.928 -12.252   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      29.481  -9.275   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.935  -9.275   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.321  -8.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.708  -9.275   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.094  -8.474   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.548  -8.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.161  -9.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.775  -8.474   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.388  -9.275   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.002  -8.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.615  -9.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.228  -8.474   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.842  -9.275   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.455  -8.474   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.069  -9.275   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.866 -10.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.608 -11.139   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.350 -10.412   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.682  -8.474   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.295  -9.275   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.093 -11.138   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.835 -10.412   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.597 -10.997   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.503 -10.334   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.856 -10.869   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.976 -10.191   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.561 -10.914   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.895 -10.144   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.228 -10.914   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.562 -10.144   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.656 -10.776   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.669 -10.191   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.229 -10.284   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      24.610 -10.412   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      39.487  -8.491   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      40.763  -6.399   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      43.937  -7.214   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      45.816  -6.381   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      44.482  -8.601   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      41.327  -7.732   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      38.365  -7.824   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      39.619  -7.050   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      45.606  -7.935   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      46.952  -7.032   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      45.011  -5.795   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      41.336  -5.550   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0      37.109  -8.550   0.000  0.00  0.00           P+0
HETATM   59  O   UNK     0      37.835  -9.806   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      36.384  -7.293   0.000  0.00  0.00           O+0
HETATM   61  P   UNK     0      48.004  -7.935   0.000  0.00  0.00           P+0
HETATM   62  O   UNK     0      48.546  -6.430   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      46.901  -9.527   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      49.894  -8.373   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6    7                                             
CONECT    4    3    5                                                       
CONECT    5    4   58                                                       
CONECT    6    3   10                                                       
CONECT    7    3                                                            
CONECT    8    9    1   12                                                  
CONECT    9    8                                                            
CONECT   10    6   11   27                                                  
CONECT   11   10                                                            
CONECT   12    8   16                                                       
CONECT   13   14   17                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   30                                                       
CONECT   27   10   28                                                       
CONECT   28   29   27                                                       
CONECT   29   28   32                                                       
CONECT   30   26   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   45                                                       
CONECT   34   35   45                                                       
CONECT   35   34   44                                                       
CONECT   36   37   44                                                       
CONECT   37   36   43                                                       
CONECT   38   39                                                            
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   37                                                       
CONECT   44   36   35                                                       
CONECT   45   34   33                                                       
CONECT   46   47   51   52                                                  
CONECT   47   46   48   53                                                  
CONECT   48   47   49   56                                                  
CONECT   49   48   50   55                                                  
CONECT   50   49   51   54                                                  
CONECT   51   50   46   57                                                  
CONECT   52   46   58                                                       
CONECT   53   47                                                            
CONECT   54   50   61                                                       
CONECT   55   49                                                            
CONECT   56   48                                                            
CONECT   57   51                                                            
CONECT   58    5   59   60   52                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   54   62   63   64                                             
CONECT   62   61                                                            
CONECT   63   61                                                            
CONECT   64   61                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  128    0
END

COMPND    HMDB0009952
HETATM    1  C1  UNL     1       2.541   1.009   9.067  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.638   2.145   8.684  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.257   2.038   9.315  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.416   0.819   8.828  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.804   0.559   9.450  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.228  -0.728   8.834  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.322  -0.909   8.138  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.331   0.092   7.847  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.561   0.478   6.477  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.007   0.225   5.336  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.868  -0.610   5.099  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.977  -1.776   4.261  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.011  -2.235   3.672  1.00  0.00           C  
HETATM   14  C14 UNL     1      -5.421  -1.842   3.585  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.680  -1.510   2.080  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.022  -0.211   1.779  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.927   0.191   0.343  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.868  -0.672  -0.274  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.422  -1.705   0.293  1.00  0.00           O  
HETATM   20  O2  UNL     1      -3.353  -0.282  -1.517  1.00  0.00           O  
HETATM   21  C19 UNL     1      -2.276  -1.058  -2.052  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.051  -0.096  -1.745  1.00  0.00           C  
HETATM   23  O3  UNL     1      -1.084   0.152  -0.384  1.00  0.00           O  
HETATM   24  C21 UNL     1      -0.243   0.943   0.387  1.00  0.00           C  
HETATM   25  O4  UNL     1       0.687   1.492  -0.283  1.00  0.00           O  
HETATM   26  C22 UNL     1      -0.423   1.110   1.815  1.00  0.00           C  
HETATM   27  C23 UNL     1      -0.987   2.374   2.387  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.329   2.761   1.815  1.00  0.00           C  
HETATM   29  C25 UNL     1      -2.332   3.307   0.438  1.00  0.00           C  
HETATM   30  C26 UNL     1      -1.909   4.768   0.391  1.00  0.00           C  
HETATM   31  C27 UNL     1      -1.727   5.147  -1.058  1.00  0.00           C  
HETATM   32  C28 UNL     1      -0.405   4.491  -1.576  1.00  0.00           C  
HETATM   33  C29 UNL     1       0.721   5.164  -0.891  1.00  0.00           C  
HETATM   34  C30 UNL     1       2.083   4.705  -0.960  1.00  0.00           C  
HETATM   35  C31 UNL     1       2.788   4.484  -2.273  1.00  0.00           C  
HETATM   36  C32 UNL     1       4.212   4.103  -1.846  1.00  0.00           C  
HETATM   37  C33 UNL     1       5.131   3.719  -2.944  1.00  0.00           C  
HETATM   38  C34 UNL     1       4.602   2.458  -3.575  1.00  0.00           C  
HETATM   39  C35 UNL     1       5.546   1.975  -4.651  1.00  0.00           C  
HETATM   40  C36 UNL     1       6.930   1.758  -4.058  1.00  0.00           C  
HETATM   41  C37 UNL     1       6.995   0.800  -2.921  1.00  0.00           C  
HETATM   42  C38 UNL     1       6.607  -0.613  -3.245  1.00  0.00           C  
HETATM   43  C39 UNL     1      -2.373  -1.369  -3.482  1.00  0.00           C  
HETATM   44  O5  UNL     1      -1.257  -2.139  -3.883  1.00  0.00           O  
HETATM   45  P1  UNL     1      -1.342  -2.518  -5.513  1.00  0.00           P  
HETATM   46  O6  UNL     1      -2.433  -1.756  -6.209  1.00  0.00           O  
HETATM   47  O7  UNL     1      -1.702  -4.175  -5.654  1.00  0.00           O  
HETATM   48  O8  UNL     1       0.133  -2.208  -6.320  1.00  0.00           O  
HETATM   49  C40 UNL     1       1.085  -3.080  -5.840  1.00  0.00           C  
HETATM   50  C41 UNL     1       1.858  -3.827  -6.865  1.00  0.00           C  
HETATM   51  O9  UNL     1       1.212  -3.641  -8.113  1.00  0.00           O  
HETATM   52  C42 UNL     1       3.274  -3.340  -7.091  1.00  0.00           C  
HETATM   53  O10 UNL     1       3.857  -4.200  -8.021  1.00  0.00           O  
HETATM   54  C43 UNL     1       4.094  -3.434  -5.823  1.00  0.00           C  
HETATM   55  O11 UNL     1       4.872  -4.578  -5.816  1.00  0.00           O  
HETATM   56  C44 UNL     1       3.183  -3.333  -4.612  1.00  0.00           C  
HETATM   57  O12 UNL     1       3.816  -3.042  -3.438  1.00  0.00           O  
HETATM   58  P2  UNL     1       3.387  -4.245  -2.295  1.00  0.00           P  
HETATM   59  O13 UNL     1       4.516  -5.162  -1.959  1.00  0.00           O  
HETATM   60  O14 UNL     1       2.128  -5.202  -2.914  1.00  0.00           O  
HETATM   61  O15 UNL     1       2.786  -3.405  -0.941  1.00  0.00           O  
HETATM   62  C45 UNL     1       2.091  -2.324  -4.959  1.00  0.00           C  
HETATM   63  O16 UNL     1       1.515  -1.829  -3.817  1.00  0.00           O  
HETATM   64  H1  UNL     1       3.141   0.725   8.174  1.00  0.00           H  
HETATM   65  H2  UNL     1       3.314   1.395   9.788  1.00  0.00           H  
HETATM   66  H3  UNL     1       2.008   0.155   9.490  1.00  0.00           H  
HETATM   67  H4  UNL     1       1.540   2.151   7.559  1.00  0.00           H  
HETATM   68  H5  UNL     1       2.160   3.087   8.930  1.00  0.00           H  
HETATM   69  H6  UNL     1       0.422   2.007  10.430  1.00  0.00           H  
HETATM   70  H7  UNL     1      -0.272   2.974   9.068  1.00  0.00           H  
HETATM   71  H8  UNL     1       0.212  -0.067   8.906  1.00  0.00           H  
HETATM   72  H9  UNL     1      -0.635   0.955   7.732  1.00  0.00           H  
HETATM   73  H10 UNL     1      -2.419   1.423   9.203  1.00  0.00           H  
HETATM   74  H11 UNL     1      -1.633   0.379  10.521  1.00  0.00           H  
HETATM   75  H12 UNL     1      -1.510  -1.564   9.004  1.00  0.00           H  
HETATM   76  H13 UNL     1      -3.457  -1.957   7.769  1.00  0.00           H  
HETATM   77  H14 UNL     1      -4.210   1.000   8.523  1.00  0.00           H  
HETATM   78  H15 UNL     1      -5.324  -0.364   8.222  1.00  0.00           H  
HETATM   79  H16 UNL     1      -5.463   1.174   6.366  1.00  0.00           H  
HETATM   80  H17 UNL     1      -4.449   0.726   4.430  1.00  0.00           H  
HETATM   81  H18 UNL     1      -2.351  -0.857   6.062  1.00  0.00           H  
HETATM   82  H19 UNL     1      -2.022   0.047   4.599  1.00  0.00           H  
HETATM   83  H20 UNL     1      -1.986  -2.328   4.126  1.00  0.00           H  
HETATM   84  H21 UNL     1      -3.752  -3.205   3.069  1.00  0.00           H  
HETATM   85  H22 UNL     1      -6.020  -2.785   3.767  1.00  0.00           H  
HETATM   86  H23 UNL     1      -5.788  -1.087   4.246  1.00  0.00           H  
HETATM   87  H24 UNL     1      -6.768  -1.460   1.955  1.00  0.00           H  
HETATM   88  H25 UNL     1      -5.284  -2.347   1.503  1.00  0.00           H  
HETATM   89  H26 UNL     1      -3.993  -0.161   2.231  1.00  0.00           H  
HETATM   90  H27 UNL     1      -5.567   0.630   2.309  1.00  0.00           H  
HETATM   91  H28 UNL     1      -5.896   0.046  -0.199  1.00  0.00           H  
HETATM   92  H29 UNL     1      -4.627   1.240   0.186  1.00  0.00           H  
HETATM   93  H30 UNL     1      -2.061  -1.904  -1.395  1.00  0.00           H  
HETATM   94  H31 UNL     1      -0.168  -0.692  -2.001  1.00  0.00           H  
HETATM   95  H32 UNL     1      -1.134   0.764  -2.399  1.00  0.00           H  
HETATM   96  H33 UNL     1       0.621   1.026   2.273  1.00  0.00           H  
HETATM   97  H34 UNL     1      -0.939   0.212   2.286  1.00  0.00           H  
HETATM   98  H35 UNL     1      -0.228   3.140   2.378  1.00  0.00           H  
HETATM   99  H36 UNL     1      -1.208   2.122   3.476  1.00  0.00           H  
HETATM  100  H37 UNL     1      -2.823   3.525   2.508  1.00  0.00           H  
HETATM  101  H38 UNL     1      -2.995   1.894   1.880  1.00  0.00           H  
HETATM  102  H39 UNL     1      -3.414   3.264   0.091  1.00  0.00           H  
HETATM  103  H40 UNL     1      -1.756   2.719  -0.265  1.00  0.00           H  
HETATM  104  H41 UNL     1      -1.165   5.060   1.092  1.00  0.00           H  
HETATM  105  H42 UNL     1      -2.851   5.341   0.702  1.00  0.00           H  
HETATM  106  H43 UNL     1      -1.651   6.219  -1.246  1.00  0.00           H  
HETATM  107  H44 UNL     1      -2.514   4.717  -1.690  1.00  0.00           H  
HETATM  108  H45 UNL     1      -0.398   4.852  -2.653  1.00  0.00           H  
HETATM  109  H46 UNL     1      -0.456   3.443  -1.622  1.00  0.00           H  
HETATM  110  H47 UNL     1       0.748   6.276  -1.275  1.00  0.00           H  
HETATM  111  H48 UNL     1       0.459   5.353   0.200  1.00  0.00           H  
HETATM  112  H49 UNL     1       2.776   5.400  -0.345  1.00  0.00           H  
HETATM  113  H50 UNL     1       2.165   3.708  -0.421  1.00  0.00           H  
HETATM  114  H51 UNL     1       2.873   5.466  -2.793  1.00  0.00           H  
HETATM  115  H52 UNL     1       2.308   3.717  -2.883  1.00  0.00           H  
HETATM  116  H53 UNL     1       4.052   3.243  -1.129  1.00  0.00           H  
HETATM  117  H54 UNL     1       4.583   4.931  -1.205  1.00  0.00           H  
HETATM  118  H55 UNL     1       6.117   3.478  -2.475  1.00  0.00           H  
HETATM  119  H56 UNL     1       5.331   4.515  -3.671  1.00  0.00           H  
HETATM  120  H57 UNL     1       4.476   1.667  -2.818  1.00  0.00           H  
HETATM  121  H58 UNL     1       3.591   2.676  -4.000  1.00  0.00           H  
HETATM  122  H59 UNL     1       5.635   2.757  -5.438  1.00  0.00           H  
HETATM  123  H60 UNL     1       5.158   1.075  -5.160  1.00  0.00           H  
HETATM  124  H61 UNL     1       7.551   1.309  -4.902  1.00  0.00           H  
HETATM  125  H62 UNL     1       7.417   2.722  -3.867  1.00  0.00           H  
HETATM  126  H63 UNL     1       8.036   0.809  -2.464  1.00  0.00           H  
HETATM  127  H64 UNL     1       6.358   1.145  -2.055  1.00  0.00           H  
HETATM  128  H65 UNL     1       7.398  -1.118  -3.870  1.00  0.00           H  
HETATM  129  H66 UNL     1       6.647  -1.170  -2.262  1.00  0.00           H  
HETATM  130  H67 UNL     1       5.620  -0.758  -3.677  1.00  0.00           H  
HETATM  131  H68 UNL     1      -2.432  -0.472  -4.139  1.00  0.00           H  
HETATM  132  H69 UNL     1      -3.269  -1.996  -3.649  1.00  0.00           H  
HETATM  133  H70 UNL     1      -1.362  -4.696  -4.866  1.00  0.00           H  
HETATM  134  H71 UNL     1       0.599  -3.811  -5.127  1.00  0.00           H  
HETATM  135  H72 UNL     1       1.825  -4.918  -6.694  1.00  0.00           H  
HETATM  136  H73 UNL     1       1.601  -2.848  -8.579  1.00  0.00           H  
HETATM  137  H74 UNL     1       3.341  -2.319  -7.495  1.00  0.00           H  
HETATM  138  H75 UNL     1       4.697  -3.809  -8.419  1.00  0.00           H  
HETATM  139  H76 UNL     1       4.777  -2.569  -5.800  1.00  0.00           H  
HETATM  140  H77 UNL     1       5.400  -4.641  -6.658  1.00  0.00           H  
HETATM  141  H78 UNL     1       2.679  -4.311  -4.523  1.00  0.00           H  
HETATM  142  H79 UNL     1       1.934  -5.968  -2.321  1.00  0.00           H  
HETATM  143  H80 UNL     1       3.349  -3.546  -0.141  1.00  0.00           H  
HETATM  144  H81 UNL     1       2.512  -1.521  -5.616  1.00  0.00           H  
HETATM  145  H82 UNL     1       2.245  -1.711  -3.132  1.00  0.00           H  
CONECT    1    2   64   65   66
CONECT    2    3   67   68
CONECT    3    4   69   70
CONECT    4    5   71   72
CONECT    5    6   73   74
CONECT    6    7    7   75
CONECT    7    8   76
CONECT    8    9   77   78
CONECT    9   10   10   79
CONECT   10   11   80
CONECT   11   12   81   82
CONECT   12   13   13   83
CONECT   13   14   84
CONECT   14   15   85   86
CONECT   15   16   87   88
CONECT   16   17   89   90
CONECT   17   18   91   92
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   43   93
CONECT   22   23   94   95
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   96   97
CONECT   27   28   98   99
CONECT   28   29  100  101
CONECT   29   30  102  103
CONECT   30   31  104  105
CONECT   31   32  106  107
CONECT   32   33  108  109
CONECT   33   34  110  111
CONECT   34   35  112  113
CONECT   35   36  114  115
CONECT   36   37  116  117
CONECT   37   38  118  119
CONECT   38   39  120  121
CONECT   39   40  122  123
CONECT   40   41  124  125
CONECT   41   42  126  127
CONECT   42  128  129  130
CONECT   43   44  131  132
CONECT   44   45
CONECT   45   46   46   47   48
CONECT   47  133
CONECT   48   49
CONECT   49   50   62  134
CONECT   50   51   52  135
CONECT   51  136
CONECT   52   53   54  137
CONECT   53  138
CONECT   54   55   56  139
CONECT   55  140
CONECT   56   57   62  141
CONECT   57   58
CONECT   58   59   59   60   61
CONECT   60  142
CONECT   61  143
CONECT   62   63  144
CONECT   63  145
END

HMDB0009952
     RDKit          3D
PIP(18:0/18:3(6Z,9Z,12Z))
145145  0  0  0  0  0  0  0  0999 V2000
    2.5413    1.0087    9.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.1451    8.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    2.0379    9.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156    0.8189    8.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043    0.5594    9.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.7275    8.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223   -0.9093    8.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.0922    7.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    0.4783    6.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0829    4.7045   -0.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    4.4841   -2.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    4.1031   -1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314    3.7193   -2.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016    2.4577   -3.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463    1.9748   -4.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9301    1.7579   -4.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9950    0.7996   -2.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6074   -0.6132   -3.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725   -1.3688   -3.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571   -2.1392   -3.8830 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0854   -3.0801   -5.8405 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.2119   -3.6407   -8.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2741   -3.3398   -7.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonate	Generator
PIP(18:0/18:3)	Lipid Annotator, HMDB
1-stearoyl-2-g-linolenoyl-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
PIP[3'](18:0/18:3(6Z,9Z,12Z))	Lipid Annotator, HMDB
1-octadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)	Lipid Annotator, HMDB
PIP(18:0/18:3(6Z,9Z,12Z))	Lipid Annotator
Phosphatidylinositol Phosphate(18:0/18:3)	Lipid Annotator, HMDB
PIP(36:3)	Lipid Annotator, HMDB
1-octadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
Phosphatidylinositol Phosphate(36:3)	Lipid Annotator, HMDB

Chemical Formula

C₄₅H₈₂O₁₆P₂

Average Molecular Weight

941.0705

Monoisotopic Molecular Weight

940.5078096

IUPAC Name

{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid

Traditional Name

[(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C45H82O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h12,14,18,20,24,26,37,40-45,48-51H,3-11,13,15-17,19,21-23,25,27-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b14-12-,20-18-,26-24-/t37-,40?,41?,42?,43?,44-,45+/m1/s1

InChI Key

KDKGDGWOVUFBBB-QEXOWQMYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositol phosphates

Direct Parent

Glycerophosphoinositol phosphates

Alternative Parents

Substituents

Glycerophosphoinositol phosphate
Diacylglycerophosphoinositol
Glycerophosphoinositol
Inositol phosphate
Cyclohexanol
Fatty acid ester
Dialkyl phosphate
Monoalkyl phosphate
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Organelle

endoplasmic reticulum (PMID: 20519312)

golgi apparatus membrane (PMID: 20519312)
cell membrane (PMID: 20519312)
Membrane (HMDB: HMDB0009952)
Extracellular (HMDB: HMDB0009952)

Cell

All cells and tissues (HMDB: HMDB0009952)

Tissue

All Tissues (HMDB: HMDB0009952)

Organ

Brain (HMDB: HMDB0009952)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Apoptosis (PMID: 11042212)

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.0065 g/L	ALOGPS
logP	6.55	ALOGPS
logP	9.56	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	243.19 m³·mol⁻¹	ChemAxon
Polarizability	104.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	283.863	30932474
DeepCCS	[M-H]-	282.21	30932474
DeepCCS	[M-2H]-	316.244	30932474
DeepCCS	[M+Na]+	290.02	30932474
AllCCS	[M+H]+	305.2	32859911
AllCCS	[M+H-H2O]+	305.6	32859911
AllCCS	[M+NH4]+	304.8	32859911
AllCCS	[M+Na]+	304.6	32859911
AllCCS	[M-H]-	302.8	32859911
AllCCS	[M+Na-2H]-	309.3	32859911
AllCCS	[M+HCOO]-	316.4	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF	splash10-0006-6211003059-e320e9f5f5511696861d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF	splash10-0rr3-9225004285-26eb2ca72bda9c3a347f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF	splash10-022c-0977500000-6481962b5426896f5dad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF	splash10-000i-0000001009-6cac759fd94e30ee7f77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF	splash10-06ui-5092006104-19b5615331c50cbba562	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PIP(18:0/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF	splash10-004i-9041000110-4179a9bba2a79c8fd634	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

All Tissues
Brain

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

24767833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750488

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

Only showing the first 10 proteins. There are 80 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB1
Uniprot ID:: Q9NQ66
Molecular weight:: 138565.805

Enzyme Details

2. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:: PLCB4
Uniprot ID:: Q15147
Molecular weight:: 136105.065

Enzyme Details

3. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB2
Uniprot ID:: Q00722
Molecular weight:: 134023.21

Enzyme Details

4. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB3
Uniprot ID:: Q01970
Molecular weight:: 138797.725

Enzyme Details

5. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2

General function:: Involved in phosphoinositide phospholipase C activity
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:: PLCG2
Uniprot ID:: P16885
Molecular weight:: 147868.67

Enzyme Details

6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1

General function:: Involved in calcium ion binding
Specific function:: Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:: PLCG1
Uniprot ID:: P19174
Molecular weight:: 148658.92

Enzyme Details

7. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Essential for trophoblast and placental development.
Gene Name:: PLCD1
Uniprot ID:: P51178
Molecular weight:: 88134.23

Enzyme Details

8. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase

General function:: Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:: Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:: PIGL
Uniprot ID:: Q9Y2B2
Molecular weight:: 28530.965

Enzyme Details

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q

General function:: Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:: Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:: PIGQ
Uniprot ID:: Q9BRB3
Molecular weight:: 65343.25

Enzyme Details

10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A

General function:: Involved in biosynthetic process
Specific function:: Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:: PIGA
Uniprot ID:: P37287
Molecular weight:: 54126.065

Only showing the first 10 proteins. There are 80 proteins in total.

Show all enzymes and transporters

Showing metabocard for PIP(18:0/18:3(6Z,9Z,12Z)) (HMDB0009952)

MOL for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

3D MOL for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

3D SDF for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

3D-SDF for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

PDB for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

3D PDB for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

SMILES for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

INCHI for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

Structure for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

3D Structure for HMDB0009952 (PIP(18:0/18:3(6Z,9Z,12Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

Enzymes