data_3PI
# 
_chem_comp.id                                    3PI 
_chem_comp.name                                  "(1S)-2-(1-HYDROXYBUTOXY)-1-{[(HYDROXY{[(2R,3S,5R,6S)-2,4,6-TRIHYDROXY-3,5-BIS(PHOSPHONOOXY)CYCLOHEXYL]OXY}PHOSPHORYL)OXY]METHYL}ETHYL BUTYRATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H35 O19 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-06-15 
_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                        636.370 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3PI 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1ZVR 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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 
3PI C1   C1   C 0 1 N N N 36.159 57.479 75.679 -2.353 -0.762 -1.774 C1   3PI 1  
3PI C2   C2   C 0 1 N N R 37.726 57.067 75.583 -3.164 -1.930 -1.209 C2   3PI 2  
3PI C3   C3   C 0 1 N N R 37.777 55.439 75.268 -3.821 -1.506 0.105  C3   3PI 3  
3PI C4   C4   C 0 1 N N N 37.024 55.072 73.915 -4.749 -0.317 -0.149 C4   3PI 4  
3PI C5   C5   C 0 1 N N S 35.492 55.576 74.036 -3.938 0.851  -0.714 C5   3PI 5  
3PI C6   C6   C 0 1 N N R 35.340 57.134 74.302 -3.281 0.427  -2.029 C6   3PI 6  
3PI O1   O1   O 0 1 N N N 36.049 58.836 75.879 -1.343 -0.386 -0.837 O1   3PI 7  
3PI O2   O2   O 0 1 N N N 38.351 57.854 74.465 -4.174 -2.307 -2.147 O2   3PI 8  
3PI O3   O3   O 0 1 N N N 39.206 54.985 75.257 -4.578 -2.597 0.633  O3   3PI 9  
3PI O4   O4   O 0 1 N N N 37.083 53.723 73.705 -5.363 0.079  1.079  O4   3PI 10 
3PI O5   O5   O 0 1 N N N 34.811 55.358 72.831 -4.805 1.962  -0.951 O5   3PI 11 
3PI O6   O6   O 0 1 N N N 34.064 57.484 74.437 -2.524 1.518  -2.556 O6   3PI 12 
3PI P1   P1   P 0 1 N N S 35.854 59.643 77.262 0.074  -0.573 -1.578 P1   3PI 13 
3PI O11  O11  O 0 1 N N N 35.771 61.148 76.852 0.178  0.463  -2.806 O11  3PI 14 
3PI O12  O12  O 0 1 N N N 37.049 59.435 78.247 0.183  -1.958 -2.091 O12  3PI 15 
3PI O13  O13  O 0 1 N N N 34.419 59.472 77.911 1.268  -0.292 -0.535 O13  3PI 16 
3PI P3   P3   P 0 1 N N N 40.192 54.855 76.522 -3.958 -2.938 2.079  P3   3PI 17 
3PI O31  O31  O 0 1 N N N 40.591 53.343 76.709 -2.506 -3.194 1.945  O31  3PI 18 
3PI O32  O32  O 0 1 N N N 39.483 55.356 77.854 -4.194 -1.693 3.072  O32  3PI 19 
3PI O33  O33  O 0 1 N N N 41.488 55.700 76.201 -4.680 -4.246 2.678  O33  3PI 20 
3PI P5   P5   P 0 1 N N N 34.064 53.992 72.389 -4.262 3.178  -0.046 P5   3PI 21 
3PI O51  O51  O 0 1 N N N 34.742 52.786 72.960 -4.179 2.743  1.366  O51  3PI 22 
3PI O52  O52  O 0 1 N N N 34.102 53.985 70.909 -2.801 3.618  -0.559 O52  3PI 23 
3PI O53  O53  O 0 1 N N N 32.644 53.957 72.839 -5.271 4.427  -0.164 O53  3PI 24 
3PI C7   C7   C 0 1 N N N 33.374 59.073 77.054 2.489  -0.587 -1.216 C7   3PI 25 
3PI C8   C8   C 0 1 N N R 32.193 59.279 77.874 3.670  -0.339 -0.275 C8   3PI 26 
3PI C9   C9   C 0 1 N N N 31.199 59.893 77.007 4.967  -0.773 -0.959 C9   3PI 27 
3PI C10  C10  C 0 1 N N R 29.532 61.575 76.226 7.232  -1.068 -0.735 C10  3PI 28 
3PI C11  C11  C 0 1 N N N 28.188 61.468 76.751 8.389  -1.200 0.256  C11  3PI 29 
3PI C12  C12  C 0 1 N N N 28.053 61.953 78.236 9.615  -1.765 -0.463 C12  3PI 30 
3PI C13  C13  C 0 1 N N N 26.509 61.881 78.443 10.773 -1.897 0.528  C13  3PI 31 
3PI C14  C14  C 0 1 N N N 32.333 56.858 79.044 4.235  1.468  1.233  C14  3PI 32 
3PI C15  C15  C 0 1 N N N 31.582 56.111 80.166 4.310  2.935  1.569  C15  3PI 33 
3PI C16  C16  C 0 1 N N N 30.783 57.012 81.110 4.906  3.109  2.967  C16  3PI 34 
3PI C17  C17  C 0 1 N N N 30.199 56.128 82.157 4.982  4.599  3.308  C17  3PI 35 
3PI O14  O14  O 0 1 N N N 31.664 58.087 78.788 3.742  1.075  0.048  O14  3PI 36 
3PI O15  O15  O 0 1 N N N 30.129 60.713 77.406 6.055  -0.650 -0.040 O15  3PI 37 
3PI O16  O16  O 0 1 N N N 29.664 61.488 75.199 7.566  -0.099 -1.731 O16  3PI 38 
3PI O17  O17  O 0 1 N N N 33.300 56.322 78.457 4.618  0.646  2.031  O17  3PI 39 
3PI H1   H1   H 0 1 N N N 35.732 56.902 76.513 -1.885 -1.065 -2.711 H1   3PI 40 
3PI H2   H2   H 0 1 N N N 38.276 57.283 76.510 -2.502 -2.778 -1.028 H2   3PI 41 
3PI H3   H3   H 0 1 N N N 37.241 54.904 76.066 -3.050 -1.219 0.821  H3   3PI 42 
3PI H4   H4   H 0 1 N N N 37.503 55.567 73.057 -5.520 -0.604 -0.864 H4   3PI 43 
3PI H5   H5   H 0 1 N N N 35.087 55.007 74.886 -3.168 1.138  0.002  H5   3PI 44 
3PI H6   H6   H 0 1 N N N 35.742 57.695 73.446 -4.052 0.140  -2.744 H6   3PI 45 
3PI HO2  HO2  H 0 1 N N N 38.483 58.752 74.745 -4.661 -3.044 -1.753 HO2  3PI 46 
3PI HO4  HO4  H 0 1 N N N 37.097 53.548 72.771 -5.938 0.829  0.875  HO4  3PI 47 
3PI HO6  HO6  H 0 1 N N N 33.854 57.567 75.360 -3.145 2.245  -2.702 HO6  3PI 48 
3PI H11  H11  H 0 1 N N N 35.754 61.689 77.633 0.103  1.351  -2.429 H11  3PI 49 
3PI H32  H32  H 0 1 N N N 40.132 55.456 78.540 -5.150 -1.560 3.131  H32  3PI 50 
3PI H33  H33  H 0 1 N N N 41.533 55.870 75.267 -4.280 -4.415 3.542  H33  3PI 51 
3PI H52  H52  H 0 1 N N N 33.215 53.984 70.569 -2.900 3.894  -1.481 H52  3PI 52 
3PI H53  H53  H 0 1 N N N 32.612 53.950 73.788 -4.910 5.131  0.391  H53  3PI 53 
3PI H71  1H7  H 0 1 N N N 33.478 58.038 76.695 2.581  0.055  -2.092 H71  3PI 54 
3PI H72  2H7  H 0 1 N N N 33.345 59.678 76.136 2.487  -1.631 -1.529 H72  3PI 55 
3PI H8   H8   H 0 1 N N N 32.479 59.942 78.704 3.532  -0.914 0.641  H8   3PI 56 
3PI H91  1H9  H 0 1 N N N 30.646 58.998 76.685 5.151  -0.138 -1.826 H91  3PI 57 
3PI H92  2H9  H 0 1 N N N 31.789 60.531 76.333 4.879  -1.810 -1.281 H92  3PI 58 
3PI H10  H10  H 0 1 N N N 30.093 62.507 76.064 7.050  -2.031 -1.211 H10  3PI 59 
3PI H111 1H11 H 0 0 N N N 27.916 60.402 76.732 8.101  -1.871 1.065  H111 3PI 60 
3PI H112 2H11 H 0 0 N N N 27.527 62.088 76.127 8.630  -0.219 0.667  H112 3PI 61 
3PI H121 1H12 H 0 0 N N N 28.483 62.948 78.422 9.904  -1.094 -1.272 H121 3PI 62 
3PI H122 2H12 H 0 0 N N N 28.598 61.305 78.938 9.375  -2.746 -0.874 H122 3PI 63 
3PI H131 1H13 H 0 0 N N N 26.118 60.967 77.972 11.013 -0.916 0.939  H131 3PI 64 
3PI H132 2H13 H 0 0 N N N 26.036 62.761 77.983 10.484 -2.569 1.337  H132 3PI 65 
3PI H133 3H13 H 0 0 N N N 26.283 61.864 79.519 11.647 -2.300 0.016  H133 3PI 66 
3PI H151 1H15 H 0 0 N N N 32.348 55.614 80.780 4.942  3.443  0.839  H151 3PI 67 
3PI H152 2H15 H 0 0 N N N 30.877 55.413 79.691 3.309  3.366  1.544  H152 3PI 68 
3PI H161 1H16 H 0 0 N N N 29.994 57.551 80.565 4.274  2.602  3.696  H161 3PI 69 
3PI H162 2H16 H 0 0 N N N 31.441 57.765 81.568 5.907  2.679  2.992  H162 3PI 70 
3PI H171 1H17 H 0 0 N N N 29.229 56.534 82.480 5.406  4.723  4.304  H171 3PI 71 
3PI H172 2H17 H 0 0 N N N 30.882 56.080 83.018 5.614  5.106  2.578  H172 3PI 72 
3PI H173 3H17 H 0 0 N N N 30.055 55.118 81.746 3.981  5.029  3.283  H173 3PI 73 
3PI H16  H16  H 0 1 N N N 28.816 61.461 74.771 7.718  0.736  -1.269 H16  3PI 74 
# 
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 
3PI C1  C2   SING N N 1  
3PI C1  C6   SING N N 2  
3PI C1  O1   SING N N 3  
3PI C1  H1   SING N N 4  
3PI C2  C3   SING N N 5  
3PI C2  O2   SING N N 6  
3PI C2  H2   SING N N 7  
3PI C3  C4   SING N N 8  
3PI C3  O3   SING N N 9  
3PI C3  H3   SING N N 10 
3PI C4  C5   SING N N 11 
3PI C4  O4   SING N N 12 
3PI C4  H4   SING N N 13 
3PI C5  C6   SING N N 14 
3PI C5  O5   SING N N 15 
3PI C5  H5   SING N N 16 
3PI C6  O6   SING N N 17 
3PI C6  H6   SING N N 18 
3PI O1  P1   SING N N 19 
3PI O2  HO2  SING N N 20 
3PI O3  P3   SING N N 21 
3PI O4  HO4  SING N N 22 
3PI O5  P5   SING N N 23 
3PI O6  HO6  SING N N 24 
3PI P1  O11  SING N N 25 
3PI P1  O12  DOUB N N 26 
3PI P1  O13  SING N N 27 
3PI O11 H11  SING N N 28 
3PI O13 C7   SING N N 29 
3PI P3  O31  DOUB N N 30 
3PI P3  O32  SING N N 31 
3PI P3  O33  SING N N 32 
3PI O32 H32  SING N N 33 
3PI O33 H33  SING N N 34 
3PI P5  O51  DOUB N N 35 
3PI P5  O52  SING N N 36 
3PI P5  O53  SING N N 37 
3PI O52 H52  SING N N 38 
3PI O53 H53  SING N N 39 
3PI C7  C8   SING N N 40 
3PI C7  H71  SING N N 41 
3PI C7  H72  SING N N 42 
3PI C8  C9   SING N N 43 
3PI C8  O14  SING N N 44 
3PI C8  H8   SING N N 45 
3PI C9  O15  SING N N 46 
3PI C9  H91  SING N N 47 
3PI C9  H92  SING N N 48 
3PI C10 C11  SING N N 49 
3PI C10 O15  SING N N 50 
3PI C10 O16  SING N N 51 
3PI C10 H10  SING N N 52 
3PI C11 C12  SING N N 53 
3PI C11 H111 SING N N 54 
3PI C11 H112 SING N N 55 
3PI C12 C13  SING N N 56 
3PI C12 H121 SING N N 57 
3PI C12 H122 SING N N 58 
3PI C13 H131 SING N N 59 
3PI C13 H132 SING N N 60 
3PI C13 H133 SING N N 61 
3PI C14 C15  SING N N 62 
3PI C14 O14  SING N N 63 
3PI C14 O17  DOUB N N 64 
3PI C15 C16  SING N N 65 
3PI C15 H151 SING N N 66 
3PI C15 H152 SING N N 67 
3PI C16 C17  SING N N 68 
3PI C16 H161 SING N N 69 
3PI C16 H162 SING N N 70 
3PI C17 H171 SING N N 71 
3PI C17 H172 SING N N 72 
3PI C17 H173 SING N N 73 
3PI O16 H16  SING N N 74 
# 
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 
3PI SMILES           ACDLabs              10.04 O=P(OC1C(O)C(OP(=O)(O)O)C(O)C(OP(=O)(O)OCC(OC(=O)CCC)COC(O)CCC)C1O)(O)O 
3PI InChI            InChI                1.02b 
;InChI=1/C17H35O19P3/c1-3-5-10(18)31-7-9(33-11(19)6-4-2)8-32-39(29,30)36-17-13(21)15(34-37(23,24)25)12(20)16(14(17)22)35-38(26,27)28/h9-10,12-18,20-22H,3-8H2,1-2H3,(H,29,30)(H2,23,24,25)(H2,26,27,28)/t9-,10-,12-,13-,14-,15-,16+,17-/m1/s1/f/h23-24,26-27,29H
;
3PI InChIKey         InChI                1.02b SEWBGVDZVBOXHU-JXRVZNDLDU 
3PI SMILES_CANONICAL CACTVS               3.341 CCC[C@H](O)OC[C@H](CO[P@@](O)(=O)O[C@@H]1[C@H](O)[C@H](O[P](O)(O)=O)[C@@H](O)[C@H](O[P](O)(O)=O)[C@H]1O)OC(=O)CCC 
3PI SMILES           CACTVS               3.341 CCC[CH](O)OC[CH](CO[P](O)(=O)O[CH]1[CH](O)[CH](O[P](O)(O)=O)[CH](O)[CH](O[P](O)(O)=O)[CH]1O)OC(=O)CCC 
3PI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC[C@H](O)OC[C@H](CO[P@](=O)(O)OC1[C@@H]([C@@H](C([C@@H]([C@H]1O)OP(=O)(O)O)O)OP(=O)(O)O)O)OC(=O)CCC 
3PI SMILES           "OpenEye OEToolkits" 1.5.0 CCCC(O)OCC(COP(=O)(O)OC1C(C(C(C(C1O)OP(=O)(O)O)O)OP(=O)(O)O)O)OC(=O)CCC 
# 
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 
3PI "SYSTEMATIC NAME" ACDLabs              10.04 "(1R)-2-{[(1R)-1-hydroxybutyl]oxy}-1-({[(S)-hydroxy{[(1S,2R,3R,4S,5S,6R)-2,4,6-trihydroxy-3,5-bis(phosphonooxy)cyclohexyl]oxy}phosphoryl]oxy}methyl)ethyl butanoate" 
3PI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R)-1-[(1R)-1-hydroxybutoxy]-3-[hydroxy-[(2R,3R,5S,6R)-2,4,6-trihydroxy-3,5-diphosphonooxy-cyclohexyl]oxy-phosphoryl]oxy-propan-2-yl] butanoate"                  
# 
