data_81A
# 
_chem_comp.id                                    81A 
_chem_comp.name                                  "2-METHANESULFONYL-BENZENESULFONIC ACID 3-METHYL-5-((1-AMIDINOAMINOOXYMETHYL-CYCLOPROPYL)METHYLOXY)-PHENYLESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H25 N3 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-02-02 
_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                        483.558 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     81A 
_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        1T4U 
_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 
81A S    S    S 0 1 N N N 20.806 -18.369 24.307 -0.743 -0.281 -5.077 S    81A 1  
81A O4   O4   O 0 1 N N N 22.093 -18.901 24.002 -0.216 -0.869 -6.258 O4   81A 2  
81A O5   O5   O 0 1 N N N 19.880 -18.349 23.219 -1.571 0.872  -5.112 O5   81A 3  
81A C16  C16  C 0 1 N N N 20.119 -19.305 25.658 -1.393 -1.536 -3.940 C16  81A 4  
81A C26  C26  C 0 1 Y N N 20.062 -15.898 25.386 0.613  0.763  -2.952 C26  81A 5  
81A C25  C25  C 0 1 Y N N 20.386 -14.673 25.968 1.747  1.218  -2.303 C25  81A 6  
81A C24  C24  C 0 1 Y N N 21.702 -14.364 26.297 2.965  1.213  -2.956 C24  81A 7  
81A C23  C23  C 0 1 Y N N 22.707 -15.291 26.023 3.051  0.753  -4.257 C23  81A 8  
81A C28  C28  C 0 1 Y N N 22.418 -16.520 25.434 1.918  0.297  -4.905 C28  81A 9  
81A C27  C27  C 0 1 Y N N 21.113 -16.821 25.105 0.700  0.298  -4.251 C27  81A 10 
81A C2   C2   C 0 1 Y N N 18.586 -13.415 21.185 1.806  -1.371 0.344  C2   81A 11 
81A C2A  C2A  C 0 1 N N N 19.671 -12.741 20.414 3.237  -1.788 0.122  C2A  81A 12 
81A C6   C6   C 0 1 Y N N 17.874 -15.208 22.645 -0.354 -0.811 -0.535 C6   81A 13 
81A C1   C1   C 0 1 Y N N 18.876 -14.571 21.895 0.965  -1.189 -0.736 C1   81A 14 
81A C3   C3   C 0 1 Y N N 17.277 -12.871 21.208 1.338  -1.164 1.628  C3   81A 15 
81A C5   C5   C 0 1 Y N N 16.567 -14.673 22.670 -0.825 -0.603 0.751  C5   81A 16 
81A C4   C4   C 0 1 Y N N 16.260 -13.500 21.969 0.021  -0.780 1.835  C4   81A 17 
81A O8   O8   O 0 1 N N N 18.162 -16.357 23.368 -1.182 -0.638 -1.598 O8   81A 18 
81A S20  S20  S 0 1 N N N 18.296 -16.285 24.950 -0.939 0.770  -2.120 S20  81A 19 
81A O21  O21  O 0 1 N N N 17.726 -17.482 25.521 -1.917 0.981  -3.130 O21  81A 20 
81A O22  O22  O 0 1 N N N 17.565 -15.160 25.469 -0.757 1.583  -0.969 O22  81A 21 
81A O7   O7   O 0 1 N N N 14.962 -12.992 22.045 -0.437 -0.577 3.097  O7   81A 22 
81A C10  C10  C 0 1 N N N 14.454 -12.431 20.802 -1.809 -0.196 2.982  C10  81A 23 
81A C14  C14  C 0 1 N N N 13.190 -11.583 21.044 -2.390 0.048  4.376  C14  81A 24 
81A CEA  C14A C 0 1 N N N 11.769 -12.124 20.723 -3.858 0.468  4.466  CEA  81A 25 
81A CEB  C14B C 0 1 N N N 12.407 -11.027 19.841 -3.439 -0.941 4.888  CEB  81A 26 
81A C15  C15  C 0 1 N N N 13.130 -10.671 22.258 -1.421 0.644  5.399  C15  81A 27 
81A O16  O16  O 0 1 N N N 13.220 -11.271 23.540 -0.106 0.137  5.161  O16  81A 28 
81A N10  N10  N 0 1 N N N 12.374 -12.220 23.704 0.740  0.722  6.134  N10  81A 29 
81A C17  C17  C 0 1 N N N 11.280 -12.016 24.418 2.080  0.417  6.151  C17  81A 30 
81A N11  N11  N 0 1 N N N 10.377 -12.944 24.524 2.572  -0.410 5.273  N11  81A 31 
81A N12  N12  N 0 1 N N N 11.114 -10.848 25.062 2.902  0.984  7.096  N12  81A 32 
81A H161 1H16 H 0 0 N N N 19.977 -20.350 25.346 -2.087 -2.186 -4.473 H161 81A 33 
81A H162 2H16 H 0 0 N N N 20.806 -19.269 26.516 -0.569 -2.131 -3.545 H162 81A 34 
81A H163 3H16 H 0 0 N N N 19.149 -18.874 25.946 -1.914 -1.046 -3.117 H163 81A 35 
81A H25  H25  H 0 1 N N N 19.605 -13.954 26.166 1.680  1.578  -1.287 H25  81A 36 
81A H24  H24  H 0 1 N N N 21.942 -13.418 26.759 3.850  1.569  -2.449 H24  81A 37 
81A H23  H23  H 0 1 N N N 23.730 -15.051 26.272 4.003  0.749  -4.767 H23  81A 38 
81A H28  H28  H 0 1 N N N 23.208 -17.230 25.237 1.985  -0.061 -5.921 H28  81A 39 
81A H21A 1H2A H 0 0 N N N 19.337 -12.575 19.379 3.303  -2.876 0.126  H21A 81A 40 
81A H22A 2H2A H 0 0 N N N 19.907 -11.774 20.882 3.582  -1.406 -0.837 H22A 81A 41 
81A H23A 3H2A H 0 0 N N N 20.569 -13.377 20.412 3.861  -1.383 0.920  H23A 81A 42 
81A H1   H1   H 0 1 N N N 19.874 -14.982 21.871 1.333  -1.351 -1.739 H1   81A 43 
81A H3   H3   H 0 1 N N N 17.055 -11.977 20.645 1.999  -1.303 2.471  H3   81A 44 
81A H5   H5   H 0 1 N N N 15.796 -15.174 23.236 -1.851 -0.305 0.910  H5   81A 45 
81A H101 1H10 H 0 0 N N N 15.231 -11.792 20.357 -1.884 0.716  2.391  H101 81A 46 
81A H102 2H10 H 0 0 N N N 14.193 -13.260 20.128 -2.367 -0.993 2.491  H102 81A 47 
81A H141 1H14 H 0 0 N N N 11.419 -13.137 20.477 -4.411 0.570  3.532  H141 81A 48 
81A H142 2H14 H 0 0 N N N 10.825 -12.252 21.273 -4.134 1.168  5.254  H142 81A 49 
81A H143 3H14 H 0 0 N N N 12.071 -10.004 19.616 -3.715 -1.766 4.232  H143 81A 50 
81A H144 4H14 H 0 0 N N N 12.603 -10.895 18.767 -3.438 -1.167 5.954  H144 81A 51 
81A H151 1H15 H 0 0 N N N 13.976 -9.973  22.173 -1.415 1.729  5.304  H151 81A 52 
81A H152 2H15 H 0 0 N N N 12.126 -10.223 22.226 -1.739 0.368  6.404  H152 81A 53 
81A HE   HE   H 0 1 N N N 12.542 -13.115 23.292 0.374  1.338  6.788  HE   81A 54 
81A HH12 HH12 H 0 0 N N N 9.612  -12.643 25.093 3.518  -0.625 5.285  HH12 81A 55 
81A HH21 HH21 H 0 0 N N N 11.885 -10.232 24.903 3.848  0.769  7.109  HH21 81A 56 
81A HH22 HH22 H 0 0 N N N 10.321 -10.624 25.628 2.536  1.600  7.750  HH22 81A 57 
# 
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 
81A S   O4   DOUB N N 1  
81A S   O5   DOUB N N 2  
81A S   C16  SING N N 3  
81A S   C27  SING N N 4  
81A C16 H161 SING N N 5  
81A C16 H162 SING N N 6  
81A C16 H163 SING N N 7  
81A C26 C25  DOUB Y N 8  
81A C26 C27  SING Y N 9  
81A C26 S20  SING N N 10 
81A C25 C24  SING Y N 11 
81A C25 H25  SING N N 12 
81A C24 C23  DOUB Y N 13 
81A C24 H24  SING N N 14 
81A C23 C28  SING Y N 15 
81A C23 H23  SING N N 16 
81A C28 C27  DOUB Y N 17 
81A C28 H28  SING N N 18 
81A C2  C2A  SING N N 19 
81A C2  C1   DOUB Y N 20 
81A C2  C3   SING Y N 21 
81A C2A H21A SING N N 22 
81A C2A H22A SING N N 23 
81A C2A H23A SING N N 24 
81A C6  C1   SING Y N 25 
81A C6  C5   DOUB Y N 26 
81A C6  O8   SING N N 27 
81A C1  H1   SING N N 28 
81A C3  C4   DOUB Y N 29 
81A C3  H3   SING N N 30 
81A C5  C4   SING Y N 31 
81A C5  H5   SING N N 32 
81A C4  O7   SING N N 33 
81A O8  S20  SING N N 34 
81A S20 O21  DOUB N N 35 
81A S20 O22  DOUB N N 36 
81A O7  C10  SING N N 37 
81A C10 C14  SING N N 38 
81A C10 H101 SING N N 39 
81A C10 H102 SING N N 40 
81A C14 CEA  SING N N 41 
81A C14 CEB  SING N N 42 
81A C14 C15  SING N N 43 
81A CEA CEB  SING N N 44 
81A CEA H141 SING N N 45 
81A CEA H142 SING N N 46 
81A CEB H143 SING N N 47 
81A CEB H144 SING N N 48 
81A C15 O16  SING N N 49 
81A C15 H151 SING N N 50 
81A C15 H152 SING N N 51 
81A O16 N10  SING N N 52 
81A N10 C17  SING N N 53 
81A N10 HE   SING N N 54 
81A C17 N11  DOUB N N 55 
81A C17 N12  SING N N 56 
81A N11 HH12 SING N N 57 
81A N12 HH21 SING N N 58 
81A N12 HH22 SING N N 59 
# 
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 
81A SMILES           ACDLabs              10.04 O=S(=O)(c1ccccc1S(=O)(=O)Oc3cc(cc(OCC2(CONC(=[N@H])N)CC2)c3)C)C                                                                                                                         
81A InChI            InChI                1.02b InChI=1/C20H25N3O7S2/c1-14-9-15(28-12-20(7-8-20)13-29-23-19(21)22)11-16(10-14)30-32(26,27)18-6-4-3-5-17(18)31(2,24)25/h3-6,9-11H,7-8,12-13H2,1-2H3,(H4,21,22,23)/f/h21,23H,22H2/b21-19+ 
81A InChIKey         InChI                1.02b FXPLUZROHGTSCH-KEINCYAKDM                                                                                                                                                               
81A SMILES_CANONICAL CACTVS               3.341 Cc1cc(OCC2(CC2)CONC(N)=N)cc(O[S](=O)(=O)c3ccccc3[S](C)(=O)=O)c1                                                                                                                         
81A SMILES           CACTVS               3.341 Cc1cc(OCC2(CC2)CONC(N)=N)cc(O[S](=O)(=O)c3ccccc3[S](C)(=O)=O)c1                                                                                                                         
81A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\N)/NOCC1(CC1)COc2cc(cc(c2)OS(=O)(=O)c3ccccc3S(=O)(=O)C)C                                                                                                                       
81A SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)NOCC1(CC1)COc2cc(cc(c2)OS(=O)(=O)c3ccccc3S(=O)(=O)C)C                                                                                                                          
# 
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 
81A "SYSTEMATIC NAME" ACDLabs              10.04 "3-({1-[(carbamimidamidooxy)methyl]cyclopropyl}methoxy)-5-methylphenyl 2-(methylsulfonyl)benzenesulfonate" 
81A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[3-[[1-(carbamimidamidooxymethyl)cyclopropyl]methoxy]-5-methyl-phenyl] 2-methylsulfonylbenzenesulfonate"  
# 
