data_PNF
# 
_chem_comp.id                                    PNF 
_chem_comp.name                                  "6-{4-[HYDROXY-(4-NITRO-PHENOXY)-PHOSPHORYL]-BUTYRYLAMINO}-HEXANOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H23 N2 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-09-14 
_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                        402.336 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PNF 
_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        1YEJ 
_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 
PNF C1   C1   C 0  1 Y N N 11.724 37.652 61.592 0.997  -0.011 -5.138 C1   PNF 1  
PNF C2   C2   C 0  1 Y N N 11.595 38.944 61.099 0.646  1.199  -5.733 C2   PNF 2  
PNF C3   C3   C 0  1 Y N N 10.383 39.581 61.241 -0.052 1.210  -6.904 C3   PNF 3  
PNF C4   C4   C 0  1 Y N N 9.323  38.924 61.867 -0.420 -0.005 -7.512 C4   PNF 4  
PNF C5   C5   C 0  1 Y N N 9.494  37.601 62.356 -0.062 -1.224 -6.904 C5   PNF 5  
PNF C6   C6   C 0  1 Y N N 10.722 36.936 62.221 0.641  -1.218 -5.736 C6   PNF 6  
PNF P1   P1   P 0  1 N N R 14.213 37.527 62.361 0.608  -0.009 -2.785 P1   PNF 7  
PNF O1   O1   O 0  1 N N N 12.946 37.045 61.446 1.692  -0.013 -3.975 O1   PNF 8  
PNF O2   O2   O 0  1 N N N 14.446 38.926 62.111 -0.308 1.309  -2.899 O2   PNF 9  
PNF O3   O3   O 0  1 N N N 13.965 37.092 63.747 -0.244 -1.214 -2.890 O3   PNF 10 
PNF C8   C8   C 0  1 N N N 15.510 36.579 61.756 1.469  -0.012 -1.178 C8   PNF 11 
PNF C9   C9   C 0  1 N N N 16.065 37.044 60.476 0.439  -0.008 -0.047 C9   PNF 12 
PNF C10  C10  C 0  1 N N N 17.270 36.154 60.214 1.162  -0.011 1.300  C10  PNF 13 
PNF C11  C11  C 0  1 N N N 17.624 36.077 58.752 0.148  -0.007 2.414  C11  PNF 14 
PNF N2   N2   N 0  1 N N N 17.329 34.903 58.052 0.557  -0.009 3.698  N2   PNF 15 
PNF O6   O6   O 0  1 N N N 18.167 37.095 58.246 -1.036 -0.002 2.155  O6   PNF 16 
PNF C12  C12  C 0  1 N N N 17.590 34.690 56.712 -0.429 -0.004 4.782  C12  PNF 17 
PNF C13  C13  C 0  1 N N N 16.589 33.739 56.035 0.293  -0.007 6.130  C13  PNF 18 
PNF C14  C14  C 0  1 N N N 17.231 32.921 54.867 -0.736 -0.003 7.261  C14  PNF 19 
PNF C15  C15  C 0  1 N N N 17.047 31.385 54.981 -0.013 -0.006 8.609  C15  PNF 20 
PNF C16  C16  C 0  1 N N N 16.760 30.638 53.667 -1.043 -0.002 9.741  C16  PNF 21 
PNF C17  C17  C 0  1 N N N 15.774 29.452 53.768 -0.331 -0.005 11.069 C17  PNF 22 
PNF O7   O7   O 0  1 N N N 15.646 28.879 54.789 0.876  -0.010 11.107 O7   PNF 23 
PNF O8   O8   O 0  1 N N N 15.099 29.045 52.837 -1.038 -0.002 12.210 O8   PNF 24 
PNF N1   N1   N 1  1 N N N 8.013  39.606 62.026 -1.108 -0.002 -8.662 N1   PNF 25 
PNF O4   O4   O 0  1 N N N 7.850  40.794 61.711 -1.425 -1.055 -9.185 O4   PNF 26 
PNF O5   O5   O -1 1 N N N 7.062  38.983 62.494 -1.417 1.053  -9.185 O5   PNF 27 
PNF H21  1H2  H 0  1 N N N 12.438 39.454 60.604 0.929  2.131  -5.266 H21  PNF 28 
PNF H31  1H3  H 0  1 N N N 10.262 40.607 60.856 -0.324 2.149  -7.364 H31  PNF 29 
PNF H51  1H5  H 0  1 N N N 8.656  37.079 62.850 -0.341 -2.160 -7.364 H51  PNF 30 
PNF H61  1H6  H 0  1 N N N 10.890 35.909 62.588 0.916  -2.152 -5.269 H61  PNF 31 
PNF HO21 1HO2 H 0  0 N N N 15.182 39.206 62.642 0.284  2.069  -2.826 HO21 PNF 32 
PNF H81  1H8  H 0  1 N N N 16.317 36.494 62.520 2.098  0.874  -1.101 H81  PNF 33 
PNF H82  2H8  H 0  1 N N N 15.204 35.509 61.679 2.090  -0.905 -1.101 H82  PNF 34 
PNF H91  1H9  H 0  1 N N N 15.324 37.055 59.642 -0.188 -0.896 -0.125 H91  PNF 35 
PNF H92  2H9  H 0  1 N N N 16.298 38.134 60.456 -0.181 0.884  -0.125 H92  PNF 36 
PNF H101 1H10 H 0  0 N N N 18.146 36.476 60.822 1.791  0.875  1.377  H101 PNF 37 
PNF H102 2H10 H 0  0 N N N 17.118 35.136 60.644 1.783  -0.904 1.378  H102 PNF 38 
PNF HN21 1HN2 H 0  0 N N N 16.886 34.138 58.561 1.504  -0.013 3.906  HN21 PNF 39 
PNF H121 1H12 H 0  0 N N N 17.647 35.658 56.162 -1.057 -0.892 4.704  H121 PNF 40 
PNF H122 2H12 H 0  0 N N N 18.635 34.331 56.565 -1.050 0.887  4.704  H122 PNF 41 
PNF H131 1H13 H 0  0 N N N 16.111 33.062 56.781 0.922  0.879  6.207  H131 PNF 42 
PNF H132 2H13 H 0  0 N N N 15.684 34.291 55.687 0.914  -0.900 6.207  H132 PNF 43 
PNF H141 1H14 H 0  0 N N N 16.852 33.285 53.883 -1.364 -0.890 7.184  H141 PNF 44 
PNF H142 2H14 H 0  0 N N N 18.311 33.176 54.762 -1.357 0.889  7.184  H142 PNF 45 
PNF H151 1H15 H 0  0 N N N 17.933 30.934 55.485 0.615  0.880  8.687  H151 PNF 46 
PNF H152 2H15 H 0  0 N N N 16.252 31.154 55.728 0.607  -0.899 8.687  H152 PNF 47 
PNF H161 1H16 H 0  0 N N N 16.410 31.357 52.890 -1.671 -0.889 9.663  H161 PNF 48 
PNF H162 2H16 H 0  0 N N N 17.717 30.297 53.207 -1.664 0.890  9.663  H162 PNF 49 
PNF HO81 1HO8 H 0  0 N N N 14.493 28.316 52.899 -0.581 -0.004 13.062 HO81 PNF 50 
# 
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 
PNF C1  C2   DOUB Y N 1  
PNF C1  C6   SING Y N 2  
PNF C1  O1   SING N N 3  
PNF C2  C3   SING Y N 4  
PNF C2  H21  SING N N 5  
PNF C3  C4   DOUB Y N 6  
PNF C3  H31  SING N N 7  
PNF C4  C5   SING Y N 8  
PNF C4  N1   SING N N 9  
PNF C5  C6   DOUB Y N 10 
PNF C5  H51  SING N N 11 
PNF C6  H61  SING N N 12 
PNF P1  O1   SING N N 13 
PNF P1  O2   SING N N 14 
PNF P1  O3   DOUB N N 15 
PNF P1  C8   SING N N 16 
PNF O2  HO21 SING N N 17 
PNF C8  C9   SING N N 18 
PNF C8  H81  SING N N 19 
PNF C8  H82  SING N N 20 
PNF C9  C10  SING N N 21 
PNF C9  H91  SING N N 22 
PNF C9  H92  SING N N 23 
PNF C10 C11  SING N N 24 
PNF C10 H101 SING N N 25 
PNF C10 H102 SING N N 26 
PNF C11 N2   SING N N 27 
PNF C11 O6   DOUB N N 28 
PNF N2  C12  SING N N 29 
PNF N2  HN21 SING N N 30 
PNF C12 C13  SING N N 31 
PNF C12 H121 SING N N 32 
PNF C12 H122 SING N N 33 
PNF C13 C14  SING N N 34 
PNF C13 H131 SING N N 35 
PNF C13 H132 SING N N 36 
PNF C14 C15  SING N N 37 
PNF C14 H141 SING N N 38 
PNF C14 H142 SING N N 39 
PNF C15 C16  SING N N 40 
PNF C15 H151 SING N N 41 
PNF C15 H152 SING N N 42 
PNF C16 C17  SING N N 43 
PNF C16 H161 SING N N 44 
PNF C16 H162 SING N N 45 
PNF C17 O7   DOUB N N 46 
PNF C17 O8   SING N N 47 
PNF O8  HO81 SING N N 48 
PNF N1  O4   DOUB N N 49 
PNF N1  O5   SING N N 50 
# 
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 
PNF SMILES           ACDLabs              10.04 O=P(Oc1ccc(cc1)[N+]([O-])=O)(O)CCCC(=O)NCCCCCC(=O)O                                                                                                         
PNF InChI            InChI                1.02b InChI=1/C16H23N2O8P/c19-15(17-11-3-1-2-6-16(20)21)5-4-12-27(24,25)26-14-9-7-13(8-10-14)18(22)23/h7-10H,1-6,11-12H2,(H,17,19)(H,20,21)(H,24,25)/f/h17,20,24H 
PNF InChIKey         InChI                1.02b WYHHVZLGTMCKOR-GDFCHNMGCK                                                                                                                                   
PNF SMILES_CANONICAL CACTVS               3.341 OC(=O)CCCCCNC(=O)CCC[P@](O)(=O)Oc1ccc(cc1)[N+]([O-])=O                                                                                                      
PNF SMILES           CACTVS               3.341 OC(=O)CCCCCNC(=O)CCC[P](O)(=O)Oc1ccc(cc1)[N+]([O-])=O                                                                                                       
PNF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[N+](=O)[O-])O[P@@](=O)(CCCC(=O)NCCCCCC(=O)O)O                                                                                                     
PNF SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[N+](=O)[O-])OP(=O)(CCCC(=O)NCCCCCC(=O)O)O                                                                                                         
# 
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 
PNF "SYSTEMATIC NAME" ACDLabs              10.04 "6-({4-[(R)-hydroxy(4-nitrophenoxy)phosphoryl]butanoyl}amino)hexanoic acid" 
PNF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "6-[4-[hydroxy-(4-nitrophenoxy)phosphoryl]butanoylamino]hexanoic acid"      
# 
