data_NA9
# 
_chem_comp.id                                    NA9 
_chem_comp.name                                  N-(CARBOXYMETHYL)-3-CYCLOHEXYL-D-ALANYL-N-({6-[AMINO(IMINO)METHYL]PYRIDIN-3-YL}METHYL)-N~2~-METHYL-L-ALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H34 N6 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2-((R)-1-(((S)-1-((6-CARBAMIMIDOYLPYRIDIN-3-YL)METHYLAMINO)-1-OXOPROPAN-2-YL)(METHYL)AMINO)-3-CYCLOHEXYL-1-OXOPROPAN-2-YLAMINO)ACETIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-27 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        446.543 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     NA9 
_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        ? 
_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 
NA9 C1   C1   C 0 1 Y N N 12.416 20.981 22.458 6.803  -4.714 3.262  C1   NA9 1  
NA9 C2   C2   C 0 1 Y N N 12.104 22.214 23.093 6.310  -3.995 4.339  C2   NA9 2  
NA9 N3   N3   N 0 1 Y N N 12.723 23.348 22.709 6.589  -2.693 4.570  N3   NA9 3  
NA9 C4   C4   C 0 1 Y N N 13.645 23.373 21.734 7.401  -2.085 3.677  C4   NA9 4  
NA9 C5   C5   C 0 1 Y N N 14.005 22.192 21.061 7.936  -2.721 2.578  C5   NA9 5  
NA9 C6   C6   C 0 1 Y N N 13.381 20.977 21.429 7.635  -4.054 2.365  C6   NA9 6  
NA9 C7   C7   C 0 1 N N N 15.046 22.225 19.972 8.832  -1.980 1.628  C7   NA9 7  
NA9 C8   C8   C 0 1 N N N 11.100 22.273 24.185 5.436  -4.634 5.308  C8   NA9 8  
NA9 N9   N9   N 0 1 N N N 10.398 21.189 24.524 5.031  -5.964 5.248  N9   NA9 9  
NA9 N10  N10  N 0 1 N N N 10.909 23.419 24.835 4.994  -3.908 6.314  N10  NA9 10 
NA9 N11  N11  N 0 1 N N N 16.375 22.122 20.599 8.088  -1.356 0.559  N11  NA9 11 
NA9 C12  C12  C 0 1 N N N 17.127 20.988 20.515 7.818  -1.999 -0.641 C12  NA9 12 
NA9 C13  C13  C 0 1 N N S 18.471 20.946 21.198 6.978  -1.139 -1.576 C13  NA9 13 
NA9 O14  O14  O 0 1 N N N 16.729 20.005 19.914 8.173  -3.143 -0.919 O14  NA9 14 
NA9 C15  C15  C 0 1 N N N 19.572 21.373 20.211 5.644  -0.786 -0.937 C15  NA9 15 
NA9 C16  C16  C 0 1 N N N 19.705 18.663 21.142 7.845  -1.681 -3.814 C16  NA9 16 
NA9 N17  N17  N 0 1 N N N 18.703 19.564 21.763 6.792  -1.876 -2.820 N17  NA9 17 
NA9 C18  C18  C 0 1 N N N 17.970 19.141 22.871 5.689  -2.707 -3.046 C18  NA9 18 
NA9 C19  C19  C 0 1 N N R 18.162 17.754 23.492 4.685  -2.861 -1.901 C19  NA9 19 
NA9 O20  O20  O 0 1 N N N 17.147 19.881 23.370 5.525  -3.334 -4.098 O20  NA9 20 
NA9 N21  N21  N 0 1 N N N 16.917 16.981 23.326 4.244  -4.236 -1.901 N21  NA9 21 
NA9 C22  C22  C 0 1 N N N 16.328 16.728 22.002 5.361  -5.155 -1.690 C22  NA9 22 
NA9 C23  C23  C 0 1 N N N 14.851 16.445 22.154 4.832  -6.556 -1.673 C23  NA9 23 
NA9 O24  O24  O 0 1 N N N 14.377 16.207 23.259 5.848  -7.431 -1.457 O24  NA9 24 
NA9 O25  O25  O 0 1 N N N 14.127 16.454 21.166 3.668  -6.895 -1.827 O25  NA9 25 
NA9 C26  C26  C 0 1 N N N 18.438 17.853 24.998 3.505  -1.903 -2.090 C26  NA9 26 
NA9 C27  C27  C 0 1 N N N 19.895 18.094 25.430 2.490  -2.000 -0.952 C27  NA9 27 
NA9 C28  C28  C 0 1 N N N 20.961 17.687 24.379 3.161  -1.715 0.398  C28  NA9 28 
NA9 C29  C29  C 0 1 N N N 22.379 17.924 24.952 2.155  -1.753 1.547  C29  NA9 29 
NA9 C30  C30  C 0 1 N N N 22.564 19.407 25.353 0.984  -0.806 1.301  C30  NA9 30 
NA9 C31  C31  C 0 1 N N N 21.497 19.817 26.392 0.312  -1.080 -0.041 C31  NA9 31 
NA9 C32  C32  C 0 1 N N N 20.078 19.586 25.814 1.315  -1.041 -1.192 C32  NA9 32 
NA9 H1   H1   H 0 1 N N N 11.925 20.067 22.757 6.555  -5.760 3.113  H1   NA9 33 
NA9 H4   H4   H 0 1 N N N 14.114 24.308 21.464 7.606  -1.039 3.886  H4   NA9 34 
NA9 H6   H6   H 0 1 N N N 13.641 20.056 20.928 8.039  -4.591 1.510  H6   NA9 35 
NA9 H71  1H7  H 0 1 N N N 14.970 23.168 19.411 9.388  -1.196 2.154  H71  NA9 36 
NA9 H72  2H7  H 0 1 N N N 14.891 21.388 19.275 9.568  -2.653 1.175  H72  NA9 37 
NA9 HN91 1HN9 H 0 0 N N N 9.780  21.428 25.273 4.421  -6.365 5.952  HN91 NA9 38 
NA9 HN92 2HN9 H 0 0 N N N 10.477 20.287 24.099 5.318  -6.581 4.497  HN92 NA9 39 
NA9 HN10 HN10 H 0 0 N N N 11.519 24.112 24.450 5.364  -2.954 6.241  HN10 NA9 40 
NA9 HN11 HN11 H 0 0 N N N 16.736 22.907 21.101 7.789  -0.394 0.688  HN11 NA9 41 
NA9 H13  H13  H 0 1 N N N 18.497 21.656 22.038 7.529  -0.227 -1.828 H13  NA9 42 
NA9 H151 1H15 H 0 0 N N N 19.143 21.475 19.203 5.081  -1.688 -0.669 H151 NA9 43 
NA9 H152 2H15 H 0 0 N N N 19.995 22.338 20.528 5.784  -0.200 -0.023 H152 NA9 44 
NA9 H153 3H15 H 0 0 N N N 20.366 20.612 20.196 5.025  -0.201 -1.626 H153 NA9 45 
NA9 H161 1H16 H 0 0 N N N 19.407 18.440 20.107 7.598  -2.219 -4.733 H161 NA9 46 
NA9 H162 2H16 H 0 0 N N N 20.689 19.154 21.142 8.799  -2.056 -3.433 H162 NA9 47 
NA9 H163 3H16 H 0 0 N N N 19.762 17.727 21.717 7.954  -0.619 -4.047 H163 NA9 48 
NA9 H19  H19  H 0 1 N N N 19.015 17.272 22.991 5.183  -2.717 -0.939 H19  NA9 49 
NA9 HN21 HN21 H 0 0 N N N 16.220 17.484 23.837 3.801  -4.460 -2.796 HN21 NA9 50 
NA9 H221 1H22 H 0 0 N N N 16.822 15.860 21.540 5.831  -4.927 -0.730 H221 NA9 51 
NA9 H222 2H22 H 0 0 N N N 16.468 17.612 21.363 6.078  -5.038 -2.507 H222 NA9 52 
NA9 HO24 HO24 H 0 0 N N N 13.443 16.053 23.177 5.533  -8.360 -1.440 HO24 NA9 53 
NA9 H261 1H26 H 0 0 N N N 17.846 18.698 25.378 2.989  -2.112 -3.034 H261 NA9 54 
NA9 H262 2H26 H 0 0 N N N 18.176 16.865 25.405 3.866  -0.869 -2.160 H262 NA9 55 
NA9 H27  H27  H 0 1 N N N 20.067 17.435 26.293 2.104  -3.027 -0.940 H27  NA9 56 
NA9 H281 1H28 H 0 0 N N N 20.828 18.294 23.471 3.644  -0.730 0.373  H281 NA9 57 
NA9 H282 2H28 H 0 0 N N N 20.841 16.621 24.134 3.951  -2.452 0.584  H282 NA9 58 
NA9 H291 1H29 H 0 0 N N N 22.518 17.291 25.841 2.655  -1.485 2.484  H291 NA9 59 
NA9 H292 2H29 H 0 0 N N N 23.121 17.670 24.181 1.778  -2.776 1.667  H292 NA9 60 
NA9 H301 1H30 H 0 0 N N N 23.565 19.542 25.789 0.251  -0.908 2.109  H301 NA9 61 
NA9 H302 2H30 H 0 0 N N N 22.454 20.037 24.458 1.343  0.231  1.324  H302 NA9 62 
NA9 H311 1H31 H 0 0 N N N 21.623 19.210 27.301 -0.172 -2.064 -0.012 H311 NA9 63 
NA9 H312 2H31 H 0 0 N N N 21.619 20.883 26.634 -0.477 -0.341 -0.216 H312 NA9 64 
NA9 H321 1H32 H 0 0 N N N 19.945 20.210 24.918 0.806  -1.304 -2.126 H321 NA9 65 
NA9 H322 2H32 H 0 0 N N N 19.331 19.857 26.575 1.690  -0.017 -1.312 H322 NA9 66 
# 
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 
NA9 C1  C6   SING Y N 1  
NA9 C1  C2   DOUB Y N 2  
NA9 C1  H1   SING N N 3  
NA9 C2  N3   SING Y N 4  
NA9 C2  C8   SING N N 5  
NA9 N3  C4   DOUB Y N 6  
NA9 C4  C5   SING Y N 7  
NA9 C4  H4   SING N N 8  
NA9 C5  C7   SING N N 9  
NA9 C5  C6   DOUB Y N 10 
NA9 C6  H6   SING N N 11 
NA9 C7  N11  SING N N 12 
NA9 C7  H71  SING N N 13 
NA9 C7  H72  SING N N 14 
NA9 C8  N9   SING N N 15 
NA9 C8  N10  DOUB N E 16 
NA9 N9  HN91 SING N N 17 
NA9 N9  HN92 SING N N 18 
NA9 N10 HN10 SING N N 19 
NA9 N11 C12  SING N N 20 
NA9 N11 HN11 SING N N 21 
NA9 C12 O14  DOUB N N 22 
NA9 C12 C13  SING N N 23 
NA9 C13 C15  SING N N 24 
NA9 C13 N17  SING N N 25 
NA9 C13 H13  SING N N 26 
NA9 C15 H151 SING N N 27 
NA9 C15 H152 SING N N 28 
NA9 C15 H153 SING N N 29 
NA9 C16 N17  SING N N 30 
NA9 C16 H161 SING N N 31 
NA9 C16 H162 SING N N 32 
NA9 C16 H163 SING N N 33 
NA9 N17 C18  SING N N 34 
NA9 C18 O20  DOUB N N 35 
NA9 C18 C19  SING N N 36 
NA9 C19 N21  SING N N 37 
NA9 C19 C26  SING N N 38 
NA9 C19 H19  SING N N 39 
NA9 N21 C22  SING N N 40 
NA9 N21 HN21 SING N N 41 
NA9 C22 C23  SING N N 42 
NA9 C22 H221 SING N N 43 
NA9 C22 H222 SING N N 44 
NA9 C23 O25  DOUB N N 45 
NA9 C23 O24  SING N N 46 
NA9 O24 HO24 SING N N 47 
NA9 C26 C27  SING N N 48 
NA9 C26 H261 SING N N 49 
NA9 C26 H262 SING N N 50 
NA9 C27 C28  SING N N 51 
NA9 C27 C32  SING N N 52 
NA9 C27 H27  SING N N 53 
NA9 C28 C29  SING N N 54 
NA9 C28 H281 SING N N 55 
NA9 C28 H282 SING N N 56 
NA9 C29 C30  SING N N 57 
NA9 C29 H291 SING N N 58 
NA9 C29 H292 SING N N 59 
NA9 C30 C31  SING N N 60 
NA9 C30 H301 SING N N 61 
NA9 C30 H302 SING N N 62 
NA9 C31 C32  SING N N 63 
NA9 C31 H311 SING N N 64 
NA9 C31 H312 SING N N 65 
NA9 C32 H321 SING N N 66 
NA9 C32 H322 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 
NA9 SMILES           ACDLabs              10.04 O=C(O)CNC(C(=O)N(C)C(C(=O)NCc1cnc(C(=[N@H])N)cc1)C)CC2CCCCC2 
NA9 InChI            InChI                1.02b 
InChI=1/C22H34N6O4/c1-14(21(31)27-12-16-8-9-17(20(23)24)25-11-16)28(2)22(32)18(26-13-19(29)30)10-15-6-4-3-5-7-15/h8-9,11,14-15,18,26H,3-7,10,12-13H2,1-2H3,(H3,23,24)(H,27,31)(H,29,30)/t14-,18+/m0/s1/f/h23,27,29H,24H2/b23-20+ 
NA9 InChIKey         InChI                1.02b XVBUQSSETBYPJB-BKQDTBLQDH 
NA9 SMILES_CANONICAL CACTVS               3.341 C[C@H](N(C)C(=O)[C@@H](CC1CCCCC1)NCC(O)=O)C(=O)NCc2ccc(nc2)C(N)=N 
NA9 SMILES           CACTVS               3.341 C[CH](N(C)C(=O)[CH](CC1CCCCC1)NCC(O)=O)C(=O)NCc2ccc(nc2)C(N)=N 
NA9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1ccc(cn1)CNC(=O)[C@H](C)N(C)C(=O)[C@@H](CC2CCCCC2)NCC(=O)O)/N 
NA9 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cn1)CNC(=O)C(C)N(C)C(=O)C(CC2CCCCC2)NCC(=O)O)N 
# 
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 
NA9 "SYSTEMATIC NAME" ACDLabs              10.04 N-(carboxymethyl)-3-cyclohexyl-D-alanyl-N-[(6-carbamimidoylpyridin-3-yl)methyl]-N~2~-methyl-L-alaninamide                                            
NA9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[(2R)-1-[[(2S)-1-[(6-carbamimidoylpyridin-3-yl)methylamino]-1-oxo-propan-2-yl]-methyl-amino]-3-cyclohexyl-1-oxo-propan-2-yl]amino]ethanoic acid" 
# 
