data_CPD
# 
_chem_comp.id                                    CPD 
_chem_comp.name                                  "[1-(3-DIMETHYLAMINO-PROPYL)-3-ETHYL-UREIDO]-[4-(2,2,2-TRIFLUORO-ACETYLAMINO)-BENZYL]PHOSPHINIC ACID-2-(2,2-DIHYDRO-ACETYLAMINO)-3-HYDROXY-1-(4-NITROPHENYL)-PROPYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H36 Cl2 F3 N6 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        743.496 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CPD 
_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        1HYX 
_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 
CPD C1   C1   C  0  1 N N N 2.660  0.993   -17.767 3.368  -0.314 5.281  C1   CPD 1  
CPD C2   C2   C  0  1 N N N 4.272  0.967   -17.848 2.129  -0.808 4.579  C2   CPD 2  
CPD C3   C3   C  0  1 N N R 6.250  -0.625  -17.773 0.987  -1.663 2.604  C3   CPD 3  
CPD C4   C4   C  0  1 N N N 6.239  -1.782  -18.850 1.380  -2.670 1.522  C4   CPD 4  
CPD C5   C5   C  0  1 N N S 6.351  -1.291  -16.411 0.260  -0.480 1.961  C5   CPD 5  
CPD C6   C6   C  0  1 Y N N 6.476  -0.392  -15.269 -0.127 0.511  3.027  C6   CPD 6  
CPD C7   C7   C  0  1 Y N N 7.711  0.343   -15.046 -1.351 0.401  3.660  C7   CPD 7  
CPD C8   C8   C  0  1 Y N N 5.354  -0.187  -14.390 0.742  1.527  3.375  C8   CPD 8  
CPD C9   C9   C  0  1 Y N N 7.810  1.265   -13.964 -1.707 1.311  4.638  C9   CPD 9  
CPD C10  C10  C  0  1 Y N N 5.449  0.724   -13.317 0.384  2.439  4.350  C10  CPD 10 
CPD C11  C11  C  0  1 Y N N 6.669  1.450   -13.096 -0.839 2.330  4.983  C11  CPD 11 
CPD C12  C12  C  0  1 N N N 6.924  -4.036  -14.474 0.733  -1.356 -0.937 C12  CPD 12 
CPD C13  C13  C  0  1 Y N N 7.845  -3.353  -13.610 0.964  -0.872 -2.346 C13  CPD 13 
CPD C14  C14  C  0  1 Y N N 9.263  -3.304  -13.880 1.811  0.195  -2.578 C14  CPD 14 
CPD C15  C15  C  0  1 Y N N 7.288  -2.568  -12.534 0.333  -1.501 -3.404 C15  CPD 15 
CPD C16  C16  C  0  1 Y N N 10.100 -2.468  -13.102 2.025  0.640  -3.868 C16  CPD 16 
CPD C17  C17  C  0  1 Y N N 8.127  -1.733  -11.758 0.538  -1.057 -4.695 C17  CPD 17 
CPD C18  C18  C  0  1 Y N N 9.549  -1.662  -12.036 1.389  0.014  -4.932 C18  CPD 18 
CPD C19  C19  C  0  1 N N N 10.076 0.094   -10.286 2.803  0.968  -6.590 C19  CPD 19 
CPD C20  C20  C  0  1 N N N 11.212 1.038   -9.661  2.997  1.568  -7.959 C20  CPD 20 
CPD C21  C21  C  0  1 N N N 4.810  -4.666  -16.589 -2.492 -2.344 -0.973 C21  CPD 21 
CPD C22  C22  C  0  1 N N N 2.973  -6.374  -16.129 -3.896 -4.203 -1.686 C22  CPD 22 
CPD C23  C23  C  0  1 N N N 1.643  -6.594  -16.694 -5.077 -4.442 -2.629 C23  CPD 23 
CPD C24  C24  C  0  1 N N N 6.764  -5.892  -17.194 -2.805 -0.134 -1.950 C24  CPD 24 
CPD C25  C25  C  0  1 N N N 7.132  -6.359  -18.569 -3.900 0.562  -1.139 C25  CPD 25 
CPD C26  C26  C  0  1 N N N 8.024  -7.529  -18.190 -4.660 1.537  -2.041 C26  CPD 26 
CPD C27  C27  C  0  1 N N N 8.290  -8.936  -20.106 -6.399 3.122  -2.182 C27  CPD 27 
CPD C28  C28  C  0  1 N N N 6.416  -9.336  -18.380 -6.685 1.170  -0.891 C28  CPD 28 
CPD N1   N1   N  0  1 N N N 4.883  -0.187  -17.841 2.191  -1.183 3.286  N1   CPD 29 
CPD N2   N2   N  1  1 N N N 6.755  2.403   -11.880 -1.220 3.305  6.029  N2   CPD 30 
CPD N3   N3   N  0  1 N N N 10.437 -0.731  -11.308 1.604  0.463  -6.240 N3   CPD 31 
CPD N4   N4   N  0  1 N N N 6.119  -4.556  -17.073 -2.077 -1.067 -1.086 N4   CPD 32 
CPD N5   N5   N  0  1 N N N 3.923  -5.669  -17.139 -3.515 -2.789 -1.728 N5   CPD 33 
CPD N6   N6   N  0  1 N N N 7.728  -8.869  -18.783 -5.711 2.206  -1.263 N6   CPD 34 
CPD O1   O1   O  0  1 N N N 4.958  2.013   -17.817 1.076  -0.867 5.178  O1   CPD 35 
CPD O2   O2   O  0  1 N N N 7.287  -1.316  -19.651 0.206  -3.138 0.857  O2   CPD 36 
CPD O3   O3   O  -1 1 N N N 7.816  2.933   -11.659 -0.455 4.203  6.333  O3   CPD 37 
CPD O4   O4   O  0  1 N N N 5.745  2.539   -11.222 -2.299 3.210  6.587  O4   CPD 38 
CPD O5   O5   O  0  1 N N N 7.360  -2.245  -16.514 -0.914 -0.949 1.295  O5   CPD 39 
CPD O6   O6   O  0  1 N N N 8.636  -4.150  -16.766 -0.631 0.911  -0.385 O6   CPD 40 
CPD O7   O7   O  0  1 N N N 4.381  -3.673  -15.899 -1.943 -3.094 -0.189 O7   CPD 41 
CPD O8   O8   O  0  1 N N N 8.957  0.120   -9.807  3.726  0.940  -5.804 O8   CPD 42 
CPD CL1  CL1  CL 0  0 N N N 2.154  1.906   -19.149 4.625  -1.607 5.262  CL1  CPD 43 
CPD CL2  CL2  CL 0  0 N N N 2.346  1.755   -16.229 2.965  0.107  6.987  CL2  CPD 44 
CPD F1   F1   F  0  1 N N N 10.762 2.247   -9.919  4.314  2.022  -8.086 F1   CPD 45 
CPD F2   F2   F  0  1 N N N 11.255 0.748   -8.367  2.742  0.598  -8.934 F2   CPD 46 
CPD F3   F3   F  0  1 N N N 12.317 0.756   -10.312 2.116  2.642  -8.127 F3   CPD 47 
CPD P    P    P  0  1 N N S 7.279  -3.807  -16.291 -0.757 -0.557 -0.257 P    CPD 48 
CPD H1   H1   H  0  1 N N N 2.118  0.018   -17.801 3.748  0.569  4.768  H1   CPD 49 
CPD H3   H3   H  0  1 N N N 7.042  0.144   -17.922 0.328  -2.145 3.327  H3   CPD 50 
CPD H41  1H4  H  0  1 N N N 6.330  -2.824  -18.464 2.039  -2.188 0.800  H41  CPD 51 
CPD H42  2H4  H  0  1 N N N 5.268  -1.978  -19.362 1.898  -3.512 1.981  H42  CPD 52 
CPD H5   H5   H  0  1 N N N 5.376  -1.774  -16.165 0.918  0.001  1.238  H5   CPD 53 
CPD H7   H7   H  0  1 N N N 8.583  0.199   -15.705 -2.029 -0.394 3.391  H7   CPD 54 
CPD H8   H8   H  0  1 N N N 4.408  -0.735  -14.540 1.698  1.612  2.881  H8   CPD 55 
CPD H9   H9   H  0  1 N N N 8.747  1.822   -13.802 -2.663 1.226  5.133  H9   CPD 56 
CPD H10  H10  H  0  1 N N N 4.577  0.867   -12.656 1.062  3.236  4.619  H10  CPD 57 
CPD H121 1H12 H  0  0 N N N 6.876  -5.120  -14.217 1.595  -1.103 -0.320 H121 CPD 58 
CPD H122 2H12 H  0  0 N N N 5.874  -3.741  -14.239 0.595  -2.437 -0.943 H122 CPD 59 
CPD H14  H14  H  0  1 N N N 9.710  -3.909  -14.686 2.305  0.681  -1.751 H14  CPD 60 
CPD H15  H15  H  0  1 N N N 6.210  -2.606  -12.302 -0.327 -2.335 -3.219 H15  CPD 61 
CPD H16  H16  H  0  1 N N N 11.179 -2.444  -13.326 2.687  1.474  -4.049 H16  CPD 62 
CPD H17  H17  H  0  1 N N N 7.676  -1.142  -10.942 0.042  -1.546 -5.520 H17  CPD 63 
CPD H221 1H22 H  0  0 N N N 2.916  -5.813  -15.166 -4.183 -4.472 -0.669 H221 CPD 64 
CPD H222 2H22 H  0  0 N N N 3.415  -7.325  -15.752 -3.051 -4.817 -1.999 H222 CPD 65 
CPD H231 1H23 H  0  0 N N N 0.962  -7.099  -15.970 -5.360 -5.494 -2.597 H231 CPD 66 
CPD H232 2H23 H  0  0 N N N 1.200  -5.642  -17.070 -5.922 -3.829 -2.316 H232 CPD 67 
CPD H233 3H23 H  0  0 N N N 1.699  -7.154  -17.656 -4.790 -4.174 -3.646 H233 CPD 68 
CPD H241 1H24 H  0  0 N N N 6.119  -6.658  -16.704 -2.114 0.611  -2.343 H241 CPD 69 
CPD H242 2H24 H  0  0 N N N 7.665  -5.927  -16.538 -3.258 -0.681 -2.776 H242 CPD 70 
CPD H251 1H25 H  0  0 N N N 6.284  -6.587  -19.256 -4.591 -0.182 -0.746 H251 CPD 71 
CPD H252 2H25 H  0  0 N N N 7.580  -5.595  -19.246 -3.447 1.110  -0.313 H252 CPD 72 
CPD H261 1H26 H  0  0 N N N 9.084  -7.262  -18.407 -3.969 2.282  -2.434 H261 CPD 73 
CPD H262 2H26 H  0  0 N N N 8.049  -7.621  -17.079 -5.113 0.989  -2.867 H262 CPD 74 
CPD H271 1H27 H  0  0 N N N 8.069  -9.935  -20.548 -7.193 3.645  -1.648 H271 CPD 75 
CPD H272 2H27 H  0  0 N N N 7.942  -8.099  -20.756 -5.686 3.847  -2.574 H272 CPD 76 
CPD H273 3H27 H  0  0 N N N 9.379  -8.700  -20.115 -6.829 2.553  -3.007 H273 CPD 77 
CPD H281 1H28 H  0  0 N N N 6.195  -10.335 -18.822 -7.489 1.620  -0.309 H281 CPD 78 
CPD H282 2H28 H  0  0 N N N 6.304  -9.343  -17.270 -7.098 0.720  -1.794 H282 CPD 79 
CPD H283 3H28 H  0  0 N N N 5.621  -8.593  -18.624 -6.190 0.403  -0.296 H283 CPD 80 
CPD HN1  HN1  H  0  1 N N N 4.143  -0.887  -17.900 3.033  -1.135 2.807  HN1  CPD 81 
CPD HN3  HN3  H  0  1 N N N 11.426 -0.647  -11.540 0.890  0.410  -6.894 HN3  CPD 82 
CPD HN5  HN5  H  0  1 N N N 3.963  -5.860  -18.140 -4.000 -2.174 -2.300 HN5  CPD 83 
CPD HO2  HO2  H  0  1 N N N 7.280  -2.011  -20.298 0.498  -3.769 0.185  HO2  CPD 84 
# 
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 
CPD C1  C2   SING N N 1  
CPD C1  CL1  SING N N 2  
CPD C1  CL2  SING N N 3  
CPD C1  H1   SING N N 4  
CPD C2  N1   SING N N 5  
CPD C2  O1   DOUB N N 6  
CPD C3  C4   SING N N 7  
CPD C3  C5   SING N N 8  
CPD C3  N1   SING N N 9  
CPD C3  H3   SING N N 10 
CPD C4  O2   SING N N 11 
CPD C4  H41  SING N N 12 
CPD C4  H42  SING N N 13 
CPD C5  C6   SING N N 14 
CPD C5  O5   SING N N 15 
CPD C5  H5   SING N N 16 
CPD C6  C7   DOUB Y N 17 
CPD C6  C8   SING Y N 18 
CPD C7  C9   SING Y N 19 
CPD C7  H7   SING N N 20 
CPD C8  C10  DOUB Y N 21 
CPD C8  H8   SING N N 22 
CPD C9  C11  DOUB Y N 23 
CPD C9  H9   SING N N 24 
CPD C10 C11  SING Y N 25 
CPD C10 H10  SING N N 26 
CPD C11 N2   SING N N 27 
CPD C12 C13  SING N N 28 
CPD C12 P    SING N N 29 
CPD C12 H121 SING N N 30 
CPD C12 H122 SING N N 31 
CPD C13 C14  DOUB Y N 32 
CPD C13 C15  SING Y N 33 
CPD C14 C16  SING Y N 34 
CPD C14 H14  SING N N 35 
CPD C15 C17  DOUB Y N 36 
CPD C15 H15  SING N N 37 
CPD C16 C18  DOUB Y N 38 
CPD C16 H16  SING N N 39 
CPD C17 C18  SING Y N 40 
CPD C17 H17  SING N N 41 
CPD C18 N3   SING N N 42 
CPD C19 C20  SING N N 43 
CPD C19 N3   SING N N 44 
CPD C19 O8   DOUB N N 45 
CPD C20 F1   SING N N 46 
CPD C20 F2   SING N N 47 
CPD C20 F3   SING N N 48 
CPD C21 N4   SING N N 49 
CPD C21 N5   SING N N 50 
CPD C21 O7   DOUB N N 51 
CPD C22 C23  SING N N 52 
CPD C22 N5   SING N N 53 
CPD C22 H221 SING N N 54 
CPD C22 H222 SING N N 55 
CPD C23 H231 SING N N 56 
CPD C23 H232 SING N N 57 
CPD C23 H233 SING N N 58 
CPD C24 C25  SING N N 59 
CPD C24 N4   SING N N 60 
CPD C24 H241 SING N N 61 
CPD C24 H242 SING N N 62 
CPD C25 C26  SING N N 63 
CPD C25 H251 SING N N 64 
CPD C25 H252 SING N N 65 
CPD C26 N6   SING N N 66 
CPD C26 H261 SING N N 67 
CPD C26 H262 SING N N 68 
CPD C27 N6   SING N N 69 
CPD C27 H271 SING N N 70 
CPD C27 H272 SING N N 71 
CPD C27 H273 SING N N 72 
CPD C28 N6   SING N N 73 
CPD C28 H281 SING N N 74 
CPD C28 H282 SING N N 75 
CPD C28 H283 SING N N 76 
CPD N1  HN1  SING N N 77 
CPD N2  O3   SING N N 78 
CPD N2  O4   DOUB N N 79 
CPD N3  HN3  SING N N 80 
CPD N4  P    SING N N 81 
CPD N5  HN5  SING N N 82 
CPD O2  HO2  SING N N 83 
CPD O5  P    SING N N 84 
CPD O6  P    DOUB N N 85 
# 
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 
CPD SMILES           ACDLabs              10.04 FC(F)(F)C(=O)Nc1ccc(cc1)CP(=O)(OC(c2ccc(cc2)[N+]([O-])=O)C(NC(=O)C(Cl)Cl)CO)N(C(=O)NCC)CCCN(C)C 
CPD InChI            InChI                1.02b 
;InChI=1/C28H36Cl2F3N6O8P/c1-4-34-27(43)38(15-5-14-37(2)3)48(46,17-18-6-10-20(11-7-18)35-26(42)28(31,32)33)47-23(22(16-40)36-25(41)24(29)30)19-8-12-21(13-9-19)39(44)45/h6-13,22-24,40H,4-5,14-17H2,1-3H3,(H,34,43)(H,35,42)(H,36,41)/t22-,23+,48+/m1/s1/f/h34-36H
;
CPD InChIKey         InChI                1.02b SITLNJAUKLVJOA-YZYQTKEMDH 
CPD SMILES_CANONICAL CACTVS               3.341 CCNC(=O)N(CCCN(C)C)[P@](=O)(Cc1ccc(NC(=O)C(F)(F)F)cc1)O[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)c2ccc(cc2)[N+]([O-])=O 
CPD SMILES           CACTVS               3.341 CCNC(=O)N(CCCN(C)C)[P](=O)(Cc1ccc(NC(=O)C(F)(F)F)cc1)O[CH]([CH](CO)NC(=O)C(Cl)Cl)c2ccc(cc2)[N+]([O-])=O 
CPD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCNC(=O)N(CCCN(C)C)[P@](=O)(Cc1ccc(cc1)NC(=O)C(F)(F)F)O[C@@H](c2ccc(cc2)[N+](=O)[O-])[C@@H](CO)NC(=O)C(Cl)Cl 
CPD SMILES           "OpenEye OEToolkits" 1.5.0 CCNC(=O)N(CCCN(C)C)P(=O)(Cc1ccc(cc1)NC(=O)C(F)(F)F)OC(c2ccc(cc2)[N+](=O)[O-])C(CO)NC(=O)C(Cl)Cl 
# 
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 
CPD "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl (S)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-P-{4-[(trifluoroacetyl)amino]benzyl}phosphonamidoate"       
CPD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[4-[[[(1S,2R)-2-(2,2-dichloroethanoylamino)-3-hydroxy-1-(4-nitrophenyl)propoxy]-(3-dimethylaminopropyl-(ethylcarbamoyl)amino)phosphoryl]methyl]phenyl]-2,2,2-trifluoro-ethanamide 
# 
