NP-MRD: Showing NP-Card for (2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid (NP0247258)

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Record Information

Version

2.0

Created at

2022-09-07 09:02:40 UTC

Updated at

2022-09-07 09:02:41 UTC

NP-MRD ID

NP0247258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

Description

PI(16:0/20:4(5Z,8Z,11Z,14Z)), also known as phosphatidylinositol(16:0/20:4) Or pi(16:0/20:4), Belongs to the class of organic compounds known as 1-phosphatidyl-1d-myo-inositols. These are lipids containing a myo-inositol attached to the phosphate group of a glycerol-3-phosphate moiety, and two acyl chains linked to the glycerol at the O1- and O2- positions, through ester linkages. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Fatty acids containing 18 and 20 carbons are the most common. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. PI(16:0/20:4(5Z,8Z,11Z,14Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. (2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid is found in Trypanosoma brucei. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) Are termed polyphosphoinositides.

Structure

MOL 3D MOL SDF PDB SMILES InChI

PI(16:0/20:4(5Z,8Z,11Z,14Z))
  Mrv1652303062020222D          

 59 59  0  0  0  0            999 V2000
10020.820210011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.104210012.3368    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10019.390510011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10018.676610012.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.962910011.9268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10017.249110012.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.535310011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.962910011.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.517410013.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.693310013.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.245710011.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.675310011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.820210013.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.245710014.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.675310013.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.247010011.9249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10022.961310012.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10022.961310013.1622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10022.247010013.5745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.532710013.1622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.532710012.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10015.821810012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.821810013.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.107610011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.393510012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.679410011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.965310012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10011.537010012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10008.680610012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10007.252310012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10005.824110012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.110010011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.248410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10012.138710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.313710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.599610011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.885410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.060410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.346310011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.632210010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.807210010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.093110011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.379010010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.664810011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.236610011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  6  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  1  1  6  0  0  0
 16 11  1  1  0  0  0
 17 12  1  6  0  0  0
 18 15  1  1  0  0  0
 19 14  1  6  0  0  0
 20 13  1  6  0  0  0
  8 39  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
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 30 31  1  0  0  0  0
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 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
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 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
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 58 59  1  0  0  0  0
M  END

     RDKit          3D

138138  0  0  0  0  0  0  0  0999 V2000
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    3.8648   -4.5904    3.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851   -5.2651    3.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0082   -6.6982   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682   -6.4207   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -3.9752   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698   -4.3464   -1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -5.4873   -3.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -5.7674   -3.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349   -3.9793   -4.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9654   -3.4292   -3.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -2.9796   -3.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8797   -2.4096   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812   -1.1046   -3.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -1.6296   -5.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659    0.6022   -4.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133   -0.0483   -2.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764   -1.4812   -3.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -0.6941   -5.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438    0.3856   -4.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5324    2.2142   -4.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    1.8546   -6.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880    1.2173   -6.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322    4.1061   -5.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303    3.5074   -5.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208    2.8270   -8.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    4.6014   -8.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    2.3677   -8.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2324    4.1650   -7.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763    2.8483  -10.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392    3.5369  -10.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    4.6512  -10.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -3.1221    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806   -2.5461    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6909   -1.0400    1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0297    2.3832   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792    2.3248   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348    3.9914    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0495    5.4330   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    4.8080   -0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306    5.9231    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488    4.4407    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    4.0137    0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8579    2.8863    2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808    1.9666    2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 41  1  0
 41 40  1  0
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 58 49  1  0
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 40118  1  0
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 39116  1  0
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  1 61  1  0
  1 62  1  0
M  END

PI(16:0/20:4(5Z,8Z,11Z,14Z))
  Mrv1652303062020222D          

 59 59  0  0  0  0            999 V2000
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10017.962910011.9268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10017.249110012.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.535310011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.962910011.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.517410013.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.693310013.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.245710011.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.675310011.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10022.961310012.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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10021.532710013.1622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.532710012.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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10015.821810013.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10011.537010012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.822910011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.108810012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.394710011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.680610012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.966410011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.252310012.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.538210011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10005.110010011.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.248410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.248410009.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10015.820210010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.106010011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.391910010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.566910010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.852810011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.138710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.313710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.599610011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.885410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.060410010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.346310011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.632210010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.807210010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.093110011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.379010010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.664810011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950710010.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.236610011.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  6  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  1  1  6  0  0  0
 16 11  1  1  0  0  0
 17 12  1  6  0  0  0
 18 15  1  1  0  0  0
 19 14  1  6  0  0  0
 20 13  1  6  0  0  0
  8 39  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247258

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C45H79O13P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(47)57-37(36-56-59(53,54)58-45-43(51)41(49)40(48)42(50)44(45)52)35-55-38(46)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,26,28,37,40-45,48-52H,3-10,12,14-16,19,21,23-25,27,29-36H2,1-2H3,(H,53,54)/b13-11-,18-17-,22-20-,28-26-/t37-,40-,41-,42+,43-,44-,45-/m1/s1

> <INCHI_KEY>
KIQYUSYSJTUGFZ-LSLODQAYSA-N

> <FORMULA>
C45H79O13P

> <MOLECULAR_WEIGHT>
859.088

> <EXACT_MASS>
858.525829602

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
99.25243401735761

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
7.03

> <JCHEM_LOGP>
9.324643923333337

> <ALOGPS_LOGS>
-6.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.360530531715522

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8332552462030662

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6458130204247565

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
233.43820000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PI(16:0/20:4(5Z,8Z,11Z,14Z))                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  O   UNK     0    8705.5318688.930   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0    8704.1958689.695   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0    8702.8628688.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8701.5308689.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8700.1978688.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8698.8658689.695   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8697.5338688.930   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8700.1978687.389   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8704.9668691.029   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8703.4278691.029   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8708.1928687.389   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8710.8618688.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8705.5318692.006   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8708.1928693.545   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8710.8618692.006   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8708.1948688.926   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8709.5288689.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8709.5288691.236   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8708.1948692.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8706.8618691.236   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8706.8618689.696   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8696.2018689.703   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8696.2018691.143   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0    8694.8688688.932   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8693.5358689.703   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8692.2028688.932   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8690.8698689.703   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8689.5368688.932   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8688.2028689.703   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8686.8698688.932   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8685.5368689.703   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8684.2038688.932   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8682.8708689.703   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8681.5378688.932   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8680.2048689.703   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8678.8718688.932   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8677.5388689.703   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8676.2058688.932   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8698.8648686.619   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0    8698.8648685.179   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0    8697.5318687.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8696.1988686.619   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0    8694.8658687.390   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0    8693.5328686.619   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0    8691.9928686.619   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0    8690.6598687.390   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0    8689.3268686.619   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0    8687.7868686.619   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0    8686.4538687.390   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0    8685.1198686.619   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0    8683.5798686.619   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0    8682.2468687.390   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0    8680.9138686.619   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0    8679.3738686.619   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0    8678.0408687.390   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0    8676.7078686.619   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0    8675.3748687.390   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0    8674.0418686.619   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0    8672.7088687.390   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3    9   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   22                                                       
CONECT    8    5   39                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11   16                                                            
CONECT   12   17                                                            
CONECT   13   20                                                            
CONECT   14   19                                                            
CONECT   15   18                                                            
CONECT   16   17   21   11                                                  
CONECT   17   16   18   12                                                  
CONECT   18   17   19   15                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   13                                                  
CONECT   21   16   20    1                                                  
CONECT   22    7   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    8   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

View in JSmol

Synonyms

Value	Source
1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-D-myo-inositol	HMDB
1-Hexadecanoyl-2-arachidonoyl-sn-glycero-3-phospho-D-myo-inositol	HMDB
1-Palmitoyl-2-arachidonoyl-sn-glycero-3-phosphoinositol	HMDB
2-Arachidonoyl-1-hexadecanoyl-sn-glycero-3-phospho-D-myo-inositol	HMDB
Phosphatidylinositol(16:0/20:4)	HMDB
Phosphatidylinositol(16:0/20:4omega6)	HMDB
Phosphatidylinositol(36:4)	HMDB
PI(16:0/20:4)	HMDB
PI(16:0/20:4omega6)	HMDB
PI(36:4)	HMDB
PIno(16:0/20:4)	HMDB
PIno(16:0/20:4omega6)	HMDB
PIno(36:4)	HMDB
1-Palmitoyl-2-arachidonoyl-gpi	HMDB
1-Palmitoyl-2-arachidonoyl-glycero-3-phospho-(1'-myo-inositol)	HMDB
1-Palmitoyl-2-arachidonoyl-glycero-3-phospho-(1’-myo-inositol)	HMDB
1-Palmitoyl-2-arachidonoyl-sn-glycero-3-phospho-D-myo-inositol	HMDB
GPI(16:0/20:4(5Z,8Z,11Z,14Z))	HMDB
GPI(16:0/20:4)	HMDB
GPI(16:0/20:4n6)	HMDB
GPI(16:0/20:4W6)	HMDB
GPI(36:4)	HMDB
PI(16:0/20:4n6)	HMDB
PI(16:0/20:4W6)	HMDB
Phosphatidylinositol(16:0/20:4(5Z,8Z,11Z,14Z))	HMDB
Phosphatidylinositol(16:0/20:4n6)	HMDB
Phosphatidylinositol(16:0/20:4W6)	HMDB
PI(16:0/20:4(5Z,8Z,11Z,14Z))	ChEBI

Chemical Formula

C₄₅H₇₉O₁₃P

Average Mass

859.0880 Da

Monoisotopic Mass

858.52583 Da

IUPAC Name

[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Traditional Name

(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C45H79O13P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(47)57-37(36-56-59(53,54)58-45-43(51)41(49)40(48)42(50)44(45)52)35-55-38(46)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,26,28,37,40-45,48-52H,3-10,12,14-16,19,21,23-25,27,29-36H2,1-2H3,(H,53,54)/b13-11-,18-17-,22-20-,28-26-/t37-,40-,41-,42+,43-,44-,45-/m1/s1

InChI Key

KIQYUSYSJTUGFZ-LSLODQAYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-phosphatidyl-1d-myo-inositols. These are lipids containing a myo-inositol attached to the phosphate group of a glycerol-3-phosphate moiety, and two acyl chains linked to the glycerol at the O1- and O2- positions, through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

1-phosphatidyl-1D-myo-inositols

Alternative Parents

Substituents

1-phosphatidyl-1d-myo-inositol
Inositol phosphate
Cyclohexanol
Fatty acid ester
Dialkyl phosphate
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

1-hexadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:73209 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	7.03	ALOGPS
logP	9.32	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	233.44 m³·mol⁻¹	ChemAxon
Polarizability	99.25 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

External Links

HMDB ID

HMDB0009789

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28639234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

73209

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid (NP0247258)

MOL for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

3D MOL for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

3D SDF for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

3D-SDF for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

PDB for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

3D PDB for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

SMILES for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

INCHI for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

Structure for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)

3D Structure for NP0247258 ((2r)-3-(hexadecanoyloxy)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid)