data_PIO
# 
_chem_comp.id                                    PIO 
_chem_comp.name                                  "L-ALPHA-D-MYOPHOSPHATIDYLINOSITOL 4,5-BISPHOSPHATE, D(+)SN1,2DI-O-OCTANOYLGLYCERYL" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H49 O19 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
"L-ALPHA-PHOSPHATIDYL-D-MYO-INOSITOL 4,5-DIPHOSPHATE, DIOCTANOYL; L-ALPHA-PHOSPHATIDYLINOSITOL 4,5-DIPHOSPHATE SODIUM SALT; PIP2; 1,2-DIACYL-SN-GLYCERO-3-PHOSPHO-(1-D-MYO-INOSITOL4,5-BISPHOSPHATE); TRIPHOSPHOINOSITIDE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-12-01 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        746.566 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PIO 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1HFA 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
PIO C1   C1   C 0 1 N N R 41.577 69.368 39.865 -5.683  -0.490 2.304  C1   PIO 1  
PIO C2   C2   C 0 1 N N R 41.964 69.258 38.378 -5.310  0.991  2.379  C2   PIO 2  
PIO C3   C3   C 0 1 N N S 42.595 67.897 38.027 -6.529  1.859  2.061  C3   PIO 3  
PIO C4   C4   C 0 1 N N R 41.858 66.631 38.552 -7.695  1.571  3.012  C4   PIO 4  
PIO C5   C5   C 0 1 N N R 41.708 66.724 40.072 -8.059  0.083  3.027  C5   PIO 5  
PIO C6   C6   C 0 1 N N S 40.972 68.045 40.434 -6.843  -0.817 3.252  C6   PIO 6  
PIO O1   O1   O 0 1 N N N 40.755 70.542 40.068 -4.579  -1.308 2.691  O1   PIO 7  
PIO O2   O2   O 0 1 N N N 40.859 69.574 37.494 -4.841  1.282  3.698  O2   PIO 8  
PIO O3   O3   O 0 1 N N N 42.696 67.909 36.604 -6.149  3.229  2.169  O3   PIO 9  
PIO O4   O4   O 0 1 N N N 42.579 65.444 38.289 -8.833  2.298  2.542  O4   PIO 10 
PIO O5   O5   O 0 1 N N N 41.032 65.610 40.664 -8.963  -0.133 4.116  O5   PIO 11 
PIO O6   O6   O 0 1 N N N 40.938 68.123 41.871 -7.246  -2.172 3.033  O6   PIO 12 
PIO P1   P1   P 0 1 N N R 41.252 72.008 40.679 -4.211  -2.661 1.886  P1   PIO 13 
PIO O11  O11  O 0 1 N N N 41.787 71.811 42.206 -4.944  -2.861 0.591  O11  PIO 14 
PIO O12  O12  O 0 1 N N N 40.130 73.147 40.361 -4.409  -3.855 2.961  O12  PIO 15 
PIO O13  O13  O 0 1 N N N 42.542 72.321 39.730 -2.602  -2.573 1.710  O13  PIO 16 
PIO P4   P4   P 0 1 N N N 42.336 64.437 37.023 -9.349  2.082  1.044  P4   PIO 17 
PIO O41  O41  O 0 1 N N N 40.741 64.228 37.037 -9.202  3.430  0.191  O41  PIO 18 
PIO O42  O42  O 0 1 N N N 42.886 65.226 35.710 -10.865 1.575  0.983  O42  PIO 19 
PIO O43  O43  O 0 1 N N N 43.309 63.206 37.357 -8.519  1.082  0.406  O43  PIO 20 
PIO P5   P5   P 0 1 N N N 41.518 64.899 42.035 -8.468  0.114  5.637  P5   PIO 21 
PIO O53  O53  O 0 1 N N N 43.073 64.495 41.909 -8.677  -1.337 6.320  O53  PIO 22 
PIO O52  O52  O 0 1 N N N 41.185 65.970 43.192 -9.651  1.003  6.288  O52  PIO 23 
PIO O51  O51  O 0 1 N N N 40.513 63.684 42.037 -7.087  0.684  5.774  O51  PIO 24 
PIO C1C  C1C  C 0 1 N N N ?      ?      ?      -2.020  -2.603 0.409  C1C  PIO 25 
PIO C2C  C2C  C 0 1 N N N ?      ?      ?      -2.083  -1.207 -0.203 C2C  PIO 26 
PIO C3C  C3C  C 0 1 N N N ?      ?      ?      -3.028  -1.183 -1.404 C3C  PIO 27 
PIO O2C  O2C  O 0 1 N N N ?      ?      ?      -0.763  -0.880 -0.700 O2C  PIO 28 
PIO O3C  O3C  O 0 1 N N N ?      ?      ?      -4.144  -0.309 -1.140 O3C  PIO 29 
PIO C1A  C1A  C 0 1 N N N ?      ?      ?      -0.482  0.413  -1.008 C1A  PIO 30 
PIO O1A  O1A  O 0 1 N N N ?      ?      ?      -1.249  1.361  -0.892 O1A  PIO 31 
PIO C2A  C2A  C 0 1 N N N ?      ?      ?      0.952   0.583  -1.464 C2A  PIO 32 
PIO C3A  C3A  C 0 1 N N N ?      ?      ?      1.429   -0.376 -2.556 C3A  PIO 33 
PIO C4A  C4A  C 0 1 N N N ?      ?      ?      2.412   -1.429 -2.038 C4A  PIO 34 
PIO C5A  C5A  C 0 1 N N N ?      ?      ?      2.009   -2.858 -2.423 C5A  PIO 35 
PIO C6A  C6A  C 0 1 N N N ?      ?      ?      1.841   -3.787 -1.217 C6A  PIO 36 
PIO C7A  C7A  C 0 1 N N N ?      ?      ?      0.478   -4.481 -1.177 C7A  PIO 37 
PIO C8A  C8A  C 0 1 N N N ?      ?      ?      0.561   -5.986 -1.380 C8A  PIO 38 
PIO C1B  C1B  C 0 1 N N N ?      ?      ?      -5.134  -0.265 -2.076 C1B  PIO 39 
PIO O1B  O1B  O 0 1 N N N ?      ?      ?      -5.183  -0.914 -3.113 O1B  PIO 40 
PIO C2B  C2B  C 0 1 N N N ?      ?      ?      -6.194  0.724  -1.660 C2B  PIO 41 
PIO C3B  C3B  C 0 1 N N N ?      ?      ?      -6.182  1.994  -2.506 C3B  PIO 42 
PIO C4B  C4B  C 0 1 N N N ?      ?      ?      -6.092  3.263  -1.657 C4B  PIO 43 
PIO C5B  C5B  C 0 1 N N N ?      ?      ?      -5.034  4.266  -2.136 C5B  PIO 44 
PIO C6B  C6B  C 0 1 N N N ?      ?      ?      -4.010  4.683  -1.075 C6B  PIO 45 
PIO C7B  C7B  C 0 1 N N N ?      ?      ?      -2.644  5.121  -1.610 C7B  PIO 46 
PIO C8B  C8B  C 0 1 N N N ?      ?      ?      -2.199  6.482  -1.093 C8B  PIO 47 
PIO H1   H1   H 0 1 N N N 42.490 69.507 40.463 -5.969  -0.759 1.280  H1   PIO 48 
PIO H2   H2   H 0 1 N N N 42.739 70.021 38.214 -4.485  1.225  1.698  H2   PIO 49 
PIO H3   H3   H 0 1 N N N 43.563 67.804 38.542 -6.841  1.697  1.021  H3   PIO 50 
PIO H4   H4   H 0 1 N N N 40.887 66.593 38.037 -7.458  1.920  4.025  H4   PIO 51 
PIO H5   H5   H 0 1 N N N 42.726 66.711 40.489 -8.568  -0.195 2.094  H5   PIO 52 
PIO H6   H6   H 0 1 N N N 39.982 67.984 39.959 -6.521  -0.758 4.298  H6   PIO 53 
PIO HO2  HO2  H 0 1 N N N 40.058 69.643 38.000 -4.654  2.236  3.735  HO2  PIO 54 
PIO HO3  HO3  H 0 1 N N N 41.825 67.912 36.224 -6.935  3.765  1.968  HO3  PIO 55 
PIO HO6  HO6  H 0 1 N N N 40.931 67.246 42.236 -6.464  -2.733 3.173  HO6  PIO 56 
PIO HP12 2HP1 H 0 0 N N N 39.912 73.609 41.162 -5.311  -4.203 3.124  HP12 PIO 57 
PIO HP42 2HP4 H 0 0 N N N 42.993 66.147 35.915 -11.579 2.142  1.346  HP42 PIO 58 
PIO HP53 3HP5 H 0 0 N N N 43.307 64.416 40.992 -8.361  -1.479 7.238  HP53 PIO 59 
PIO HP52 2HP5 H 0 0 N N N 41.119 65.524 44.028 -9.545  1.336  7.204  HP52 PIO 60 
PIO HC11 1HC1 H 0 0 N N N ?      ?      ?      -2.595  -3.317 -0.189 HC11 PIO 61 
PIO HC12 2HC1 H 0 0 N N N ?      ?      ?      -0.984  -2.952 0.468  HC12 PIO 62 
PIO HC2  HC2  H 0 1 N N N ?      ?      ?      -2.398  -0.469 0.544  HC2  PIO 63 
PIO HC31 1HC3 H 0 0 N N N ?      ?      ?      -2.521  -0.774 -2.286 HC31 PIO 64 
PIO HC32 2HC3 H 0 0 N N N ?      ?      ?      -3.389  -2.186 -1.661 HC32 PIO 65 
PIO H2A1 1H2A H 0 0 N N N ?      ?      ?      1.077   1.616  -1.808 H2A1 PIO 66 
PIO H2A2 2H2A H 0 0 N N N ?      ?      ?      1.578   0.442  -0.575 H2A2 PIO 67 
PIO H3A1 1H3A H 0 0 N N N ?      ?      ?      0.546   -0.880 -2.966 H3A1 PIO 68 
PIO H3A2 2H3A H 0 0 N N N ?      ?      ?      1.886   0.180  -3.381 H3A2 PIO 69 
PIO H4A1 1H4A H 0 0 N N N ?      ?      ?      2.496   -1.350 -0.948 H4A1 PIO 70 
PIO H4A2 2H4A H 0 0 N N N ?      ?      ?      3.410   -1.239 -2.447 H4A2 PIO 71 
PIO H5A1 1H5A H 0 0 N N N ?      ?      ?      1.080   -2.819 -3.002 H5A1 PIO 72 
PIO H5A2 2H5A H 0 0 N N N ?      ?      ?      2.781   -3.265 -3.088 H5A2 PIO 73 
PIO H6A1 1H6A H 0 0 N N N ?      ?      ?      2.621   -4.558 -1.250 H6A1 PIO 74 
PIO H6A2 2H6A H 0 0 N N N ?      ?      ?      1.983   -3.230 -0.284 H6A2 PIO 75 
PIO H7A1 1H7A H 0 0 N N N ?      ?      ?      -0.150  -4.058 -1.970 H7A1 PIO 76 
PIO H7A2 2H7A H 0 0 N N N ?      ?      ?      -0.024  -4.266 -0.226 H7A2 PIO 77 
PIO H8A1 1H8A H 0 0 N N N ?      ?      ?      -0.445  -6.413 -1.439 H8A1 PIO 78 
PIO H8A2 2H8A H 0 0 N N N ?      ?      ?      1.080   -6.475 -0.551 H8A2 PIO 79 
PIO H8A3 3H8A H 0 0 N N N ?      ?      ?      1.087   -6.229 -2.309 H8A3 PIO 80 
PIO H2B1 1H2B H 0 0 N N N ?      ?      ?      -7.169  0.227  -1.732 H2B1 PIO 81 
PIO H2B2 2H2B H 0 0 N N N ?      ?      ?      -6.048  0.963  -0.600 H2B2 PIO 82 
PIO H3B1 1H3B H 0 0 N N N ?      ?      ?      -7.102  2.020  -3.102 H3B1 PIO 83 
PIO H3B2 2H3B H 0 0 N N N ?      ?      ?      -5.339  1.959  -3.204 H3B2 PIO 84 
PIO H4B1 1H4B H 0 0 N N N ?      ?      ?      -7.063  3.773  -1.668 H4B1 PIO 85 
PIO H4B2 2H4B H 0 0 N N N ?      ?      ?      -5.892  2.996  -0.612 H4B2 PIO 86 
PIO H5B1 1H5B H 0 0 N N N ?      ?      ?      -5.576  5.170  -2.444 H5B1 PIO 87 
PIO H5B2 2H5B H 0 0 N N N ?      ?      ?      -4.546  3.886  -3.039 H5B2 PIO 88 
PIO H6B1 1H6B H 0 0 N N N ?      ?      ?      -3.869  3.866  -0.359 H6B1 PIO 89 
PIO H6B2 2H6B H 0 0 N N N ?      ?      ?      -4.431  5.519  -0.501 H6B2 PIO 90 
PIO H7B1 1H7B H 0 0 N N N ?      ?      ?      -1.901  4.378  -1.295 H7B1 PIO 91 
PIO H7B2 2H7B H 0 0 N N N ?      ?      ?      -2.632  5.129  -2.703 H7B2 PIO 92 
PIO H8B1 1H8B H 0 0 N N N ?      ?      ?      -1.177  6.691  -1.425 H8B1 PIO 93 
PIO H8B2 2H8B H 0 0 N N N ?      ?      ?      -2.211  6.510  0.001  H8B2 PIO 94 
PIO H8B3 3H8B H 0 0 N N N ?      ?      ?      -2.838  7.286  -1.468 H8B3 PIO 95 
PIO HO1  HO1  H 0 1 N N N 40.434 64.187 37.935 -9.703  4.228  0.461  HO1  PIO 96 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
PIO C1  C2   SING N N 1  
PIO C1  C6   SING N N 2  
PIO C1  O1   SING N N 3  
PIO C1  H1   SING N N 4  
PIO C2  C3   SING N N 5  
PIO C2  O2   SING N N 6  
PIO C2  H2   SING N N 7  
PIO C3  C4   SING N N 8  
PIO C3  O3   SING N N 9  
PIO C3  H3   SING N N 10 
PIO C4  C5   SING N N 11 
PIO C4  O4   SING N N 12 
PIO C4  H4   SING N N 13 
PIO C5  C6   SING N N 14 
PIO C5  O5   SING N N 15 
PIO C5  H5   SING N N 16 
PIO C6  O6   SING N N 17 
PIO C6  H6   SING N N 18 
PIO O1  P1   SING N N 19 
PIO O2  HO2  SING N N 20 
PIO O3  HO3  SING N N 21 
PIO O4  P4   SING N N 22 
PIO O5  P5   SING N N 23 
PIO O6  HO6  SING N N 24 
PIO P1  O11  DOUB N N 25 
PIO P1  O12  SING N N 26 
PIO P1  O13  SING N N 27 
PIO O12 HP12 SING N N 28 
PIO O13 C1C  SING N N 29 
PIO P4  O41  SING N N 30 
PIO P4  O42  SING N N 31 
PIO P4  O43  DOUB N N 32 
PIO O42 HP42 SING N N 33 
PIO P5  O53  SING N N 34 
PIO P5  O52  SING N N 35 
PIO P5  O51  DOUB N N 36 
PIO O53 HP53 SING N N 37 
PIO O52 HP52 SING N N 38 
PIO C1C C2C  SING N N 39 
PIO C1C HC11 SING N N 40 
PIO C1C HC12 SING N N 41 
PIO C2C C3C  SING N N 42 
PIO C2C O2C  SING N N 43 
PIO C2C HC2  SING N N 44 
PIO C3C O3C  SING N N 45 
PIO C3C HC31 SING N N 46 
PIO C3C HC32 SING N N 47 
PIO O2C C1A  SING N N 48 
PIO O3C C1B  SING N N 49 
PIO C1A O1A  DOUB N N 50 
PIO C1A C2A  SING N N 51 
PIO C2A C3A  SING N N 52 
PIO C2A H2A1 SING N N 53 
PIO C2A H2A2 SING N N 54 
PIO C3A C4A  SING N N 55 
PIO C3A H3A1 SING N N 56 
PIO C3A H3A2 SING N N 57 
PIO C4A C5A  SING N N 58 
PIO C4A H4A1 SING N N 59 
PIO C4A H4A2 SING N N 60 
PIO C5A C6A  SING N N 61 
PIO C5A H5A1 SING N N 62 
PIO C5A H5A2 SING N N 63 
PIO C6A C7A  SING N N 64 
PIO C6A H6A1 SING N N 65 
PIO C6A H6A2 SING N N 66 
PIO C7A C8A  SING N N 67 
PIO C7A H7A1 SING N N 68 
PIO C7A H7A2 SING N N 69 
PIO C8A H8A1 SING N N 70 
PIO C8A H8A2 SING N N 71 
PIO C8A H8A3 SING N N 72 
PIO C1B O1B  DOUB N N 73 
PIO C1B C2B  SING N N 74 
PIO C2B C3B  SING N N 75 
PIO C2B H2B1 SING N N 76 
PIO C2B H2B2 SING N N 77 
PIO C3B C4B  SING N N 78 
PIO C3B H3B1 SING N N 79 
PIO C3B H3B2 SING N N 80 
PIO C4B C5B  SING N N 81 
PIO C4B H4B1 SING N N 82 
PIO C4B H4B2 SING N N 83 
PIO C5B C6B  SING N N 84 
PIO C5B H5B1 SING N N 85 
PIO C5B H5B2 SING N N 86 
PIO C6B C7B  SING N N 87 
PIO C6B H6B1 SING N N 88 
PIO C6B H6B2 SING N N 89 
PIO C7B C8B  SING N N 90 
PIO C7B H7B1 SING N N 91 
PIO C7B H7B2 SING N N 92 
PIO C8B H8B1 SING N N 93 
PIO C8B H8B2 SING N N 94 
PIO C8B H8B3 SING N N 95 
PIO HO1 O41  SING N N 96 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
PIO SMILES           ACDLabs              10.04 O=P(OC1C(O)C(O)C(OP(=O)(O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC)C(O)C1OP(=O)(O)O)(O)O 
PIO InChI            InChI                1.02b 
;InChI=1/C25H49O19P3/c1-3-5-7-9-11-13-18(26)39-15-17(41-19(27)14-12-10-8-6-4-2)16-40-47(37,38)44-23-20(28)21(29)24(42-45(31,32)33)25(22(23)30)43-46(34,35)36/h17,20-25,28-30H,3-16H2,1-2H3,(H,37,38)(H2,31,32,33)(H2,34,35,36)/t17?,20-,21+,22+,23-,24-,25-/m1/s1/f/h31-32,34-35,37H
;
PIO InChIKey         InChI                1.02b XLNCEHRXXWQMPK-QAYYHLCJDB 
PIO SMILES_CANONICAL CACTVS               3.341 CCCCCCCC(=O)OCC(CO[P@](O)(=O)O[C@@H]1[C@H](O)[C@H](O)[C@@H](O[P](O)(O)=O)[C@H](O[P](O)(O)=O)[C@H]1O)OC(=O)CCCCCCC 
PIO SMILES           CACTVS               3.341 CCCCCCCC(=O)OCC(CO[P](O)(=O)O[CH]1[CH](O)[CH](O)[CH](O[P](O)(O)=O)[CH](O[P](O)(O)=O)[CH]1O)OC(=O)CCCCCCC 
PIO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)OP(=O)(O)O)OP(=O)(O)O)O)O)OC(=O)CCCCCCC 
PIO SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCCCC(=O)OCC(COP(=O)(O)OC1C(C(C(C(C1O)OP(=O)(O)O)OP(=O)(O)O)O)O)OC(=O)CCCCCCC 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
PIO "SYSTEMATIC NAME" ACDLabs              10.04 "3-{[(R)-hydroxy{[(1R,2R,3S,4R,5R,6S)-2,3,6-trihydroxy-4,5-bis(phosphonooxy)cyclohexyl]oxy}phosphoryl]oxy}propane-1,2-diyl dioctanoate"   
PIO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S)-3-[hydroxy-[(1R,2R,3S,4R,5R,6S)-2,3,6-trihydroxy-4,5-diphosphonooxy-cyclohexyl]oxy-phosphoryl]oxy-2-octanoyloxy-propyl] octanoate" 
# 
