data_BX3
# 
_chem_comp.id                                    BX3 
_chem_comp.name                                  "(+)-2-[4-[(-1-ACETIMIDOYL-4-PIPERIDINYL)OXY]-3-(7-AMIDINO-2-NAPHTHYL)PROPIONIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H30 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         BX5633 
_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                        458.552 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BX3 
_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        1MTV 
_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 
BX3 N1   N1   N 0 1 N N N 46.382 18.230 54.974 -3.900 0.988  -7.005 N1   BX3 1  
BX3 C2   C2   C 0 1 N N N 45.587 17.937 54.001 -2.885 0.503  -7.661 C2   BX3 2  
BX3 N3   N3   N 0 1 N N N 45.120 16.771 53.755 -2.918 0.448  -9.038 N3   BX3 3  
BX3 C4   C4   C 0 1 Y N N 45.194 19.070 53.082 -1.696 0.011  -6.929 C4   BX3 4  
BX3 C5   C5   C 0 1 Y N N 44.657 18.831 51.796 -0.604 -0.509 -7.643 C5   BX3 5  
BX3 C6   C6   C 0 1 Y N N 44.257 19.894 50.975 0.497  -0.966 -6.994 C6   BX3 6  
BX3 C7   C7   C 0 1 Y N N 44.406 21.222 51.430 0.556  -0.921 -5.590 C7   BX3 7  
BX3 C8   C8   C 0 1 Y N N 44.948 21.480 52.715 -0.539 -0.396 -4.858 C8   BX3 8  
BX3 C9   C9   C 0 1 Y N N 45.346 20.401 53.538 -1.669 0.070  -5.547 C9   BX3 9  
BX3 C10  C10  C 0 1 Y N N 44.020 22.309 50.627 1.685  -1.387 -4.896 C10  BX3 10 
BX3 C11  C11  C 0 1 Y N N 44.184 23.624 51.089 1.713  -1.331 -3.536 C11  BX3 11 
BX3 C12  C12  C 0 1 Y N N 45.087 22.799 53.159 -0.476 -0.359 -3.454 C12  BX3 12 
BX3 C13  C13  C 0 1 Y N N 44.729 23.872 52.353 0.636  -0.815 -2.817 C13  BX3 13 
BX3 C14  C14  C 0 1 N N N 44.925 25.275 52.948 0.702  -0.768 -1.312 C14  BX3 14 
BX3 C15  C15  C 0 1 N N S 43.764 26.281 52.630 1.310  0.564  -0.870 C15  BX3 15 
BX3 C16  C16  C 0 1 Y N N 42.440 25.895 53.280 1.377  0.611  0.634  C16  BX3 16 
BX3 C17  C17  C 0 1 Y N N 42.322 25.477 54.614 0.703  1.602  1.323  C17  BX3 17 
BX3 C18  C18  C 0 1 Y N N 41.057 25.096 55.114 0.762  1.647  2.703  C18  BX3 18 
BX3 C19  C19  C 0 1 Y N N 39.907 25.163 54.262 1.499  0.698  3.396  C19  BX3 19 
BX3 C20  C20  C 0 1 Y N N 40.047 25.588 52.919 2.178  -0.291 2.701  C20  BX3 20 
BX3 C21  C21  C 0 1 Y N N 41.311 25.939 52.450 2.111  -0.336 1.322  C21  BX3 21 
BX3 C22  C22  C 0 1 N N N 44.087 27.726 52.956 2.700  0.695  -1.439 C22  BX3 22 
BX3 O23  O23  O 0 1 N N N 43.423 28.603 52.338 3.647  0.815  -0.698 O23  BX3 23 
BX3 O24  O24  O 0 1 N N N 45.001 27.997 53.771 2.885  0.679  -2.768 O24  BX3 24 
BX3 O25  O25  O 0 1 N N N 38.606 24.801 54.667 1.559  0.740  4.753  O25  BX3 25 
BX3 C26  C26  C 0 1 N N N 38.208 24.873 56.022 0.434  0.004  5.239  C26  BX3 26 
BX3 C27  C27  C 0 1 N N N 37.854 26.354 56.279 -0.778 0.931  5.337  C27  BX3 27 
BX3 N28  N28  N 0 1 N N N 36.400 25.559 58.147 -1.638 -0.536 7.086  N28  BX3 28 
BX3 C29  C29  C 0 1 N N N 36.638 24.138 57.776 -0.436 -1.380 7.126  C29  BX3 29 
BX3 C30  C30  C 0 1 N N N 36.917 24.045 56.249 0.757  -0.563 6.623  C30  BX3 30 
BX3 C31  C31  C 0 1 N N N 35.287 25.929 58.764 -2.416 -0.375 8.202  C31  BX3 31 
BX3 N32  N32  N 0 1 N N N 34.220 25.209 58.907 -3.534 0.270  8.123  N32  BX3 32 
BX3 C33  C33  C 0 1 N N N 35.110 27.313 59.394 -1.970 -0.951 9.521  C33  BX3 33 
BX3 C34  C34  C 0 1 N N N 37.486 26.511 57.784 -1.993 0.126  5.824  C34  BX3 34 
BX3 HN1  HN1  H 0 1 N N N 46.896 17.801 54.204 -4.679 1.310  -7.484 HN1  BX3 35 
BX3 HN31 1HN3 H 0 0 N N N 44.491 16.539 52.985 -3.697 0.770  -9.518 HN31 BX3 36 
BX3 HN32 2HN3 H 0 0 N N N 44.665 16.451 54.610 -2.162 0.087  -9.527 HN32 BX3 37 
BX3 H5   H5   H 0 1 N N N 44.548 17.797 51.426 -0.642 -0.547 -8.722 H5   BX3 38 
BX3 H6   H6   H 0 1 N N N 43.828 19.687 49.979 1.329  -1.364 -7.557 H6   BX3 39 
BX3 H9   H9   H 0 1 N N N 45.774 20.597 54.535 -2.510 0.472  -5.002 H9   BX3 40 
BX3 H10  H10  H 0 1 N N N 43.586 22.129 49.629 2.528  -1.789 -5.439 H10  BX3 41 
BX3 H11  H11  H 0 1 N N N 43.881 24.471 50.451 2.582  -1.690 -3.007 H11  BX3 42 
BX3 H12  H12  H 0 1 N N N 45.487 22.997 54.167 -1.305 0.033  -2.884 H12  BX3 43 
BX3 H141 1H14 H 0 0 N N N 45.093 25.210 54.048 1.322  -1.588 -0.950 H141 BX3 44 
BX3 H142 2H14 H 0 0 N N N 45.905 25.699 52.629 -0.302 -0.863 -0.901 H142 BX3 45 
BX3 H15  H15  H 0 1 N N N 43.652 26.204 51.523 0.690  1.384  -1.233 H15  BX3 46 
BX3 H17  H17  H 0 1 N N N 43.213 25.448 55.262 0.130  2.341  0.783  H17  BX3 47 
BX3 H18  H18  H 0 1 N N N 40.968 24.750 56.157 0.236  2.422  3.241  H18  BX3 48 
BX3 H20  H20  H 0 1 N N N 39.177 25.645 52.242 2.752  -1.032 3.239  H20  BX3 49 
BX3 H21  H21  H 0 1 N N N 41.420 26.258 51.399 2.635  -1.110 0.781  H21  BX3 50 
BX3 HO4  HO4  H 0 1 N N N 45.203 28.902 53.975 3.777  0.764  -3.133 HO4  BX3 51 
BX3 H26  H26  H 0 1 N N N 39.014 24.486 56.688 0.212  -0.813 4.554  H26  BX3 52 
BX3 H271 1H27 H 0 0 N N N 38.662 27.051 55.958 -0.566 1.736  6.041  H271 BX3 53 
BX3 H272 2H27 H 0 0 N N N 37.054 26.729 55.599 -0.993 1.354  4.355  H272 BX3 54 
BX3 H291 1H29 H 0 0 N N N 37.449 23.673 58.382 -0.252 -1.704 8.151  H291 BX3 55 
BX3 H292 2H29 H 0 0 N N N 35.801 23.472 58.094 -0.579 -2.251 6.486  H292 BX3 56 
BX3 H301 1H30 H 0 0 N N N 36.058 24.365 55.613 0.955  0.255  7.315  H301 BX3 57 
BX3 H302 2H30 H 0 0 N N N 36.978 23.000 55.864 1.635  -1.205 6.558  H302 BX3 58 
BX3 HN3  HN3  H 0 1 N N N 33.308 25.653 58.794 -3.788 0.700  7.292  HN3  BX3 59 
BX3 H331 1H33 H 0 0 N N N 34.173 27.624 59.913 -2.712 -0.724 10.286 H331 BX3 60 
BX3 H332 2H33 H 0 0 N N N 35.954 27.467 60.105 -1.863 -2.032 9.428  H332 BX3 61 
BX3 H333 3H33 H 0 0 N N N 35.322 28.070 58.604 -1.012 -0.514 9.803  H333 BX3 62 
BX3 H341 1H34 H 0 0 N N N 38.376 26.399 58.445 -2.261 -0.619 5.075  H341 BX3 63 
BX3 H342 2H34 H 0 0 N N N 37.221 27.563 58.041 -2.834 0.799  5.990  H342 BX3 64 
# 
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 
BX3 N1  C2   DOUB N N 1  
BX3 N1  HN1  SING N N 2  
BX3 C2  N3   SING N N 3  
BX3 C2  C4   SING N N 4  
BX3 N3  HN31 SING N N 5  
BX3 N3  HN32 SING N N 6  
BX3 C4  C5   DOUB Y N 7  
BX3 C4  C9   SING Y N 8  
BX3 C5  C6   SING Y N 9  
BX3 C5  H5   SING N N 10 
BX3 C6  C7   DOUB Y N 11 
BX3 C6  H6   SING N N 12 
BX3 C7  C8   SING Y N 13 
BX3 C7  C10  SING Y N 14 
BX3 C8  C9   DOUB Y N 15 
BX3 C8  C12  SING Y N 16 
BX3 C9  H9   SING N N 17 
BX3 C10 C11  DOUB Y N 18 
BX3 C10 H10  SING N N 19 
BX3 C11 C13  SING Y N 20 
BX3 C11 H11  SING N N 21 
BX3 C12 C13  DOUB Y N 22 
BX3 C12 H12  SING N N 23 
BX3 C13 C14  SING N N 24 
BX3 C14 C15  SING N N 25 
BX3 C14 H141 SING N N 26 
BX3 C14 H142 SING N N 27 
BX3 C15 C16  SING N N 28 
BX3 C15 C22  SING N N 29 
BX3 C15 H15  SING N N 30 
BX3 C16 C17  DOUB Y N 31 
BX3 C16 C21  SING Y N 32 
BX3 C17 C18  SING Y N 33 
BX3 C17 H17  SING N N 34 
BX3 C18 C19  DOUB Y N 35 
BX3 C18 H18  SING N N 36 
BX3 C19 C20  SING Y N 37 
BX3 C19 O25  SING N N 38 
BX3 C20 C21  DOUB Y N 39 
BX3 C20 H20  SING N N 40 
BX3 C21 H21  SING N N 41 
BX3 C22 O23  DOUB N N 42 
BX3 C22 O24  SING N N 43 
BX3 O24 HO4  SING N N 44 
BX3 O25 C26  SING N N 45 
BX3 C26 C27  SING N N 46 
BX3 C26 C30  SING N N 47 
BX3 C26 H26  SING N N 48 
BX3 C27 C34  SING N N 49 
BX3 C27 H271 SING N N 50 
BX3 C27 H272 SING N N 51 
BX3 N28 C29  SING N N 52 
BX3 N28 C31  SING N N 53 
BX3 N28 C34  SING N N 54 
BX3 C29 C30  SING N N 55 
BX3 C29 H291 SING N N 56 
BX3 C29 H292 SING N N 57 
BX3 C30 H301 SING N N 58 
BX3 C30 H302 SING N N 59 
BX3 C31 N32  DOUB N N 60 
BX3 C31 C33  SING N N 61 
BX3 N32 HN3  SING N N 62 
BX3 C33 H331 SING N N 63 
BX3 C33 H332 SING N N 64 
BX3 C33 H333 SING N N 65 
BX3 C34 H341 SING N N 66 
BX3 C34 H342 SING N N 67 
# 
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 
BX3 SMILES           ACDLabs              10.04 O=C(O)C(c2ccc(OC1CCN(C(=[N@H])C)CC1)cc2)Cc4cc3cc(C(=[N@H])N)ccc3cc4 
BX3 InChI            InChI                1.02b 
InChI=1/C27H30N4O3/c1-17(28)31-12-10-24(11-13-31)34-23-8-6-20(7-9-23)25(27(32)33)15-18-2-3-19-4-5-21(26(29)30)16-22(19)14-18/h2-9,14,16,24-25,28H,10-13,15H2,1H3,(H3,29,30)(H,32,33)/b28-17+/t25-/m0/s1/f/h29,32H,30H2/b28-17+,29-26? 
BX3 InChIKey         InChI                1.02b FZLDAJVXFYWRCX-BQWXPFTNDW 
BX3 SMILES_CANONICAL CACTVS               3.341 CC(=N)N1CCC(CC1)Oc2ccc(cc2)[C@H](Cc3ccc4ccc(cc4c3)C(N)=N)C(O)=O 
BX3 SMILES           CACTVS               3.341 CC(=N)N1CCC(CC1)Oc2ccc(cc2)[CH](Cc3ccc4ccc(cc4c3)C(N)=N)C(O)=O 
BX3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=N)N1CCC(CC1)Oc2ccc(cc2)[C@H](Cc3ccc4ccc(cc4c3)C(=N)N)C(=O)O 
BX3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(=N)N1CCC(CC1)Oc2ccc(cc2)C(Cc3ccc4ccc(cc4c3)C(=N)N)C(=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 
BX3 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-({1-[(1E)-ethanimidoyl]piperidin-4-yl}oxy)phenyl]propanoic acid" 
BX3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-(1-ethanimidoylpiperidin-4-yl)oxyphenyl]propanoic acid"          
# 
