data_RA4
# 
_chem_comp.id                                    RA4 
_chem_comp.name                                  N-(4-NITROBENZOYL)-L-LEUCYL-N-(4-{[AMINO(IMINO)METHYL]AMINO}BUTYL)-L-PROLINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H35 N7 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         1-GUANIDINO-4-(N-NITRO-BENZOYLAMINO-L-LEUCYL-L-PROLYLAMINO)BUTANE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-02-03 
_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                        489.568 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RA4 
_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        1YPM 
_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 
RA4 C27  C27  C 0  1 Y N N 17.464 -17.318 24.074 4.922   -0.575 0.177  C27  RA4 1  
RA4 C26  C26  C 0  1 N N N 18.868 -16.772 24.152 4.084   0.643  0.182  C26  RA4 2  
RA4 O25  O25  O 0  1 N N N 19.550 -17.157 25.096 4.607   1.740  0.226  O25  RA4 3  
RA4 N24  N24  N 0  1 N N N 19.295 -15.861 23.269 2.742   0.538  0.138  N24  RA4 4  
RA4 C23  C23  C 0  1 N N S 19.263 -14.448 23.538 1.911   1.745  0.143  C23  RA4 5  
RA4 C22  C22  C 0  1 N N N 20.596 -13.886 24.018 1.770   2.273  -1.286 C22  RA4 6  
RA4 C21  C21  C 0  1 N N N 20.781 -13.907 25.532 3.139   2.725  -1.800 C21  RA4 7  
RA4 C20  C20  C 0  1 N N N 19.491 -14.310 26.258 3.021   3.136  -3.269 C20  RA4 8  
RA4 C19  C19  C 0  1 N N N 21.335 -12.570 26.056 3.625   3.917  -0.974 C19  RA4 9  
RA4 C18  C18  C 0  1 N N N 18.645 -13.608 22.443 0.548   1.415  0.694  C18  RA4 10 
RA4 O17  O17  O 0  1 N N N 17.598 -13.077 22.829 0.295   0.282  1.047  O17  RA4 11 
RA4 N16  N16  N 0  1 N N N 19.303 -13.046 21.395 -0.390  2.378  0.793  N16  RA4 12 
RA4 C15  C15  C 0  1 N N N 20.379 -13.761 20.735 -0.217  3.788  0.402  C15  RA4 13 
RA4 C14  C14  C 0  1 N N N 20.940 -12.685 19.768 -1.260  4.564  1.245  C14  RA4 14 
RA4 C13  C13  C 0  1 N N N 19.759 -11.719 19.511 -2.452  3.570  1.258  C13  RA4 15 
RA4 C12  C12  C 0  1 N N S 18.872 -11.802 20.775 -1.756  2.193  1.304  C12  RA4 16 
RA4 C11  C11  C 0  1 N N N 17.436 -11.857 20.319 -2.507  1.210  0.444  C11  RA4 17 
RA4 O10  O10  O 0  1 N N N 17.064 -12.804 19.632 -1.960  0.694  -0.507 O10  RA4 18 
RA4 N9   N9   N 0  1 N N N 16.793 -10.758 20.415 -3.788  0.904  0.732  N9   RA4 19 
RA4 C8   C8   C 0  1 N N N 15.432 -10.908 19.933 -4.518  -0.052 -0.104 C8   RA4 20 
RA4 C7   C7   C 0  1 N N N 14.556 -9.949  20.768 -5.940  -0.220 0.437  C7   RA4 21 
RA4 C6   C6   C 0  1 N N N 13.293 -10.693 21.213 -6.702  -1.219 -0.436 C6   RA4 22 
RA4 C5   C5   C 0  1 N N N 12.584 -9.902  22.342 -8.124  -1.387 0.104  C5   RA4 23 
RA4 N4   N4   N 0  1 N N N 11.998 -10.916 23.174 -8.854  -2.343 -0.732 N4   RA4 24 
RA4 C2   C2   C 0  1 N N N 11.172 -10.577 24.064 -10.161 -2.655 -0.438 C2   RA4 25 
RA4 N1   N1   N 0  1 N N N 10.885 -9.391  24.419 -10.749 -2.101 0.585  N1   RA4 26 
RA4 N3   N3   N 0  1 N N N 10.586 -11.562 24.648 -10.846 -3.553 -1.222 N3   RA4 27 
RA4 C28  C28  C 0  1 Y N N 17.002 -18.044 25.179 6.313   -0.469 0.223  C28  RA4 28 
RA4 C29  C29  C 0  1 Y N N 15.851 -18.825 25.081 7.089   -1.610 0.218  C29  RA4 29 
RA4 C30  C30  C 0  1 Y N N 15.137 -18.896 23.881 6.491   -2.857 0.167  C30  RA4 30 
RA4 N31  N31  N 1  1 N N N 14.024 -19.664 23.814 7.330   -4.077 0.161  N31  RA4 31 
RA4 O32  O32  O -1 1 N N N 13.592 -20.376 24.946 8.543   -3.981 0.201  O32  RA4 32 
RA4 O33  O33  O 0  1 N N N 13.379 -19.757 22.795 6.806   -5.175 0.117  O33  RA4 33 
RA4 C34  C34  C 0  1 Y N N 15.602 -18.169 22.783 5.113   -2.969 0.121  C34  RA4 34 
RA4 C35  C35  C 0  1 Y N N 16.761 -17.389 22.873 4.325   -1.836 0.132  C35  RA4 35 
RA4 H24  H24  H 0  1 N N N 19.645 -16.244 22.391 2.325   -0.337 0.103  H24  RA4 36 
RA4 H23  H23  H 0  1 N N N 18.559 -14.364 24.398 2.381   2.506  0.767  H23  RA4 37 
RA4 H221 1H22 H 0  0 N N N 20.748 -12.855 23.622 1.082   3.118  -1.295 H221 RA4 38 
RA4 H222 2H22 H 0  0 N N N 21.442 -14.410 23.516 1.384   1.482  -1.929 H222 RA4 39 
RA4 H21  H21  H 0  1 N N N 21.542 -14.690 25.758 3.850   1.904  -1.708 H21  RA4 40 
RA4 H201 1H20 H 0  0 N N N 19.102 -15.285 25.883 3.996   3.457  -3.636 H201 RA4 41 
RA4 H202 2H20 H 0  0 N N N 19.626 -14.325 27.365 2.674   2.286  -3.858 H202 RA4 42 
RA4 H203 3H20 H 0  0 N N N 18.638 -13.656 25.962 2.309   3.956  -3.361 H203 RA4 43 
RA4 H191 1H19 H 0  0 N N N 20.698 -11.712 25.736 2.914   4.738  -1.066 H191 RA4 44 
RA4 H192 2H19 H 0  0 N N N 21.470 -12.585 27.163 3.709   3.624  0.072  H192 RA4 45 
RA4 H193 3H19 H 0  0 N N N 22.280 -12.289 25.535 4.600   4.239  -1.341 H193 RA4 46 
RA4 H151 1H15 H 0  0 N N N 20.080 -14.720 20.251 0.791   4.128  0.640  H151 RA4 47 
RA4 H152 2H15 H 0  0 N N N 21.131 -14.218 21.420 -0.420  3.915  -0.661 H152 RA4 48 
RA4 H141 1H14 H 0  0 N N N 21.390 -13.105 18.838 -0.891  4.743  2.255  H141 RA4 49 
RA4 H142 2H14 H 0  0 N N N 21.862 -12.181 20.140 -1.537  5.500  0.760  H142 RA4 50 
RA4 H131 1H13 H 0  0 N N N 19.209 -11.926 18.564 -3.071  3.722  2.142  H131 RA4 51 
RA4 H132 2H13 H 0  0 N N N 20.077 -10.681 19.255 -3.045  3.668  0.348  H132 RA4 52 
RA4 H12  H12  H 0  1 N N N 18.957 -10.946 21.484 -1.717  1.832  2.332  H12  RA4 53 
RA4 HN9  HN9  H 0  1 N N N 17.265 -9.937  20.795 -4.226  1.316  1.493  HN9  RA4 54 
RA4 H81  1H8  H 0  1 N N N 15.072 -11.963 19.954 -4.560  0.318  -1.128 H81  RA4 55 
RA4 H82  2H8  H 0  1 N N N 15.335 -10.748 18.834 -4.007  -1.015 -0.086 H82  RA4 56 
RA4 H71  1H7  H 0  1 N N N 14.324 -9.003  20.225 -5.898  -0.591 1.461  H71  RA4 57 
RA4 H72  2H7  H 0  1 N N N 15.112 -9.503  21.626 -6.451  0.742  0.420  H72  RA4 58 
RA4 H61  1H6  H 0  1 N N N 13.511 -11.745 21.512 -6.745  -0.848 -1.460 H61  RA4 59 
RA4 H62  2H6  H 0  1 N N N 12.609 -10.905 20.358 -6.191  -2.181 -0.419 H62  RA4 60 
RA4 H51  1H5  H 0  1 N N N 11.860 -9.137  21.977 -8.082  -1.758 1.128  H51  RA4 61 
RA4 H52  2H5  H 0  1 N N N 13.248 -9.192  22.888 -8.635  -0.424 0.087  H52  RA4 62 
RA4 HN4  HN4  H 0  1 N N N 12.746 -11.455 23.610 -8.416  -2.755 -1.493 HN4  RA4 63 
RA4 HN1  HN1  H 0  1 N N N 11.594 -8.715  24.134 -11.671 -2.322 0.792  HN1  RA4 64 
RA4 HN31 1HN3 H 0  0 N N N 11.275 -12.210 25.030 -10.408 -3.965 -1.983 HN31 RA4 65 
RA4 HN32 2HN3 H 0  0 N N N 9.918  -11.288 25.368 -11.768 -3.773 -1.015 HN32 RA4 66 
RA4 H28  H28  H 0  1 N N N 17.550 -18.000 26.135 6.781   0.503  0.261  H28  RA4 67 
RA4 H29  H29  H 0  1 N N N 15.502 -19.392 25.961 8.165   -1.530 0.253  H29  RA4 68 
RA4 H34  H34  H 0  1 N N N 15.046 -18.211 21.831 4.652   -3.945 0.081  H34  RA4 69 
RA4 H35  H35  H 0  1 N N N 17.122 -16.828 21.994 3.249   -1.925 0.097  H35  RA4 70 
# 
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 
RA4 C27 C26  SING N N 1  
RA4 C27 C28  DOUB Y N 2  
RA4 C27 C35  SING Y N 3  
RA4 C26 O25  DOUB N N 4  
RA4 C26 N24  SING N N 5  
RA4 N24 C23  SING N N 6  
RA4 N24 H24  SING N N 7  
RA4 C23 C22  SING N N 8  
RA4 C23 C18  SING N N 9  
RA4 C23 H23  SING N N 10 
RA4 C22 C21  SING N N 11 
RA4 C22 H221 SING N N 12 
RA4 C22 H222 SING N N 13 
RA4 C21 C20  SING N N 14 
RA4 C21 C19  SING N N 15 
RA4 C21 H21  SING N N 16 
RA4 C20 H201 SING N N 17 
RA4 C20 H202 SING N N 18 
RA4 C20 H203 SING N N 19 
RA4 C19 H191 SING N N 20 
RA4 C19 H192 SING N N 21 
RA4 C19 H193 SING N N 22 
RA4 C18 O17  DOUB N N 23 
RA4 C18 N16  SING N N 24 
RA4 N16 C15  SING N N 25 
RA4 N16 C12  SING N N 26 
RA4 C15 C14  SING N N 27 
RA4 C15 H151 SING N N 28 
RA4 C15 H152 SING N N 29 
RA4 C14 C13  SING N N 30 
RA4 C14 H141 SING N N 31 
RA4 C14 H142 SING N N 32 
RA4 C13 C12  SING N N 33 
RA4 C13 H131 SING N N 34 
RA4 C13 H132 SING N N 35 
RA4 C12 C11  SING N N 36 
RA4 C12 H12  SING N N 37 
RA4 C11 O10  DOUB N N 38 
RA4 C11 N9   SING N N 39 
RA4 N9  C8   SING N N 40 
RA4 N9  HN9  SING N N 41 
RA4 C8  C7   SING N N 42 
RA4 C8  H81  SING N N 43 
RA4 C8  H82  SING N N 44 
RA4 C7  C6   SING N N 45 
RA4 C7  H71  SING N N 46 
RA4 C7  H72  SING N N 47 
RA4 C6  C5   SING N N 48 
RA4 C6  H61  SING N N 49 
RA4 C6  H62  SING N N 50 
RA4 C5  N4   SING N N 51 
RA4 C5  H51  SING N N 52 
RA4 C5  H52  SING N N 53 
RA4 N4  C2   SING N N 54 
RA4 N4  HN4  SING N N 55 
RA4 C2  N1   DOUB N N 56 
RA4 C2  N3   SING N N 57 
RA4 N1  HN1  SING N N 58 
RA4 N3  HN31 SING N N 59 
RA4 N3  HN32 SING N N 60 
RA4 C28 C29  SING Y N 61 
RA4 C28 H28  SING N N 62 
RA4 C29 C30  DOUB Y N 63 
RA4 C29 H29  SING N N 64 
RA4 C30 N31  SING N N 65 
RA4 C30 C34  SING Y N 66 
RA4 N31 O32  SING N N 67 
RA4 N31 O33  DOUB N N 68 
RA4 C34 C35  DOUB Y N 69 
RA4 C34 H34  SING N N 70 
RA4 C35 H35  SING N N 71 
# 
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 
RA4 SMILES           ACDLabs              10.04 O=C(NCCCCNC(=[N@H])N)C2N(C(=O)C(NC(=O)c1ccc([N+]([O-])=O)cc1)CC(C)C)CCC2 
RA4 InChI            InChI                1.02b 
InChI=1/C23H35N7O5/c1-15(2)14-18(28-20(31)16-7-9-17(10-8-16)30(34)35)22(33)29-13-5-6-19(29)21(32)26-11-3-4-12-27-23(24)25/h7-10,15,18-19H,3-6,11-14H2,1-2H3,(H,26,32)(H,28,31)(H4,24,25,27)/t18-,19-/m0/s1/f/h24,26-28H,25H2/b24-23- 
RA4 InChIKey         InChI                1.02b FIZYZWLGMGGGBJ-JVKRQGPCDI 
RA4 SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@H](NC(=O)c1ccc(cc1)[N+]([O-])=O)C(=O)N2CCC[C@H]2C(=O)NCCCCNC(N)=N 
RA4 SMILES           CACTVS               3.341 CC(C)C[CH](NC(=O)c1ccc(cc1)[N+]([O-])=O)C(=O)N2CCC[CH]2C(=O)NCCCCNC(N)=N 
RA4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)NCCCCNC(=N)N)NC(=O)c2ccc(cc2)[N+](=O)[O-] 
RA4 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC(C(=O)N1CCCC1C(=O)NCCCCNC(=N)N)NC(=O)c2ccc(cc2)[N+](=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 
RA4 "SYSTEMATIC NAME" ACDLabs              10.04 N-[(4-nitrophenyl)carbonyl]-L-leucyl-N-(4-carbamimidamidobutyl)-L-prolinamide                                        
RA4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-(4-carbamimidamidobutyl)-1-[(2S)-4-methyl-2-[(4-nitrophenyl)carbonylamino]pentanoyl]pyrrolidine-2-carboxamide 
# 
