data_74M
# 
_chem_comp.id                                    74M 
_chem_comp.name                                  "METHYL N-({(2S,3S)-3-[(PROPYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H31 N3 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CA074ME, N-(L-3-TRANS-PROPYLCARBAMOYLOXIRANE-2-CARBONYL)-L-ISOLEUCYL-L-PROLINE METHYL ESTER" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-05 
_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                        397.466 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     74M 
_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        2DC9 
_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 
74M C2   C2   C 0 1 N N S 12.734 18.418 -7.537  3.320  1.035  1.350  C2   74M 1  
74M O1   O1   O 0 1 N N N 12.079 17.403 -7.139  3.560  2.442  1.281  O1   74M 2  
74M C3   C3   C 0 1 N N S 11.838 19.638 -7.280  2.871  1.883  0.159  C3   74M 3  
74M C4   C4   C 0 1 N N N 10.451 19.563 -7.904  1.400  2.178  0.020  C4   74M 4  
74M O4   O4   O 0 1 N N N 10.338 19.749 -9.115  0.992  3.312  0.164  O4   74M 5  
74M N1   N1   N 0 1 N N N 9.452  19.281 -7.047  0.536  1.183  -0.262 N1   74M 6  
74M C5   C5   C 0 1 N N S 8.109  18.656 -7.350  -0.898 1.464  -0.364 C5   74M 7  
74M C6   C6   C 0 1 N N N 7.320  19.567 -8.387  -1.678 0.308  0.210  C6   74M 8  
74M O5   O5   O 0 1 N N N 7.519  20.795 -8.336  -1.122 -0.746 0.435  O5   74M 9  
74M C14  C14  C 0 1 N N S 7.282  18.479 -6.015  -1.277 1.655  -1.833 C14  74M 10 
74M C16  C16  C 0 1 N N N 7.522  19.598 -4.960  -0.497 0.661  -2.696 C16  74M 11 
74M C15  C15  C 0 1 N N N 7.599  17.116 -5.340  -0.937 3.083  -2.266 C15  74M 12 
74M C17  C17  C 0 1 N N N 6.263  20.123 -4.244  -0.963 -0.762 -2.383 C17  74M 13 
74M N2   N2   N 0 1 N N N 6.411  19.072 -9.308  -2.992 0.447  0.473  N2   74M 14 
74M C7   C7   C 0 1 N N S 5.195  19.798 -9.786  -3.833 -0.532 1.178  C7   74M 15 
74M C8   C8   C 0 1 N N N 4.014  20.029 -8.782  -3.873 -1.831 0.415  C8   74M 16 
74M O6   O6   O 0 1 N N N 2.987  20.630 -9.153  -3.384 -1.899 -0.688 O6   74M 17 
74M C20  C20  C 0 1 N N N 4.808  18.999 -11.047 -5.252 0.067  1.270  C20  74M 18 
74M C19  C19  C 0 1 N N N 5.365  17.581 -10.859 -5.002 1.589  1.105  C19  74M 19 
74M C18  C18  C 0 1 N N N 6.569  17.731 -9.923  -3.826 1.603  0.096  C18  74M 20 
74M O7   O7   O 0 1 N N N 4.298  19.493 -7.498  -4.452 -2.912 0.961  O7   74M 21 
74M C9   C9   C 0 1 N N N 3.090  19.832 -6.754  -4.491 -4.164 0.226  C9   74M 22 
74M N3   N3   N 0 1 N N N 14.384 17.845 -5.813  4.392  -0.939 0.312  N3   74M 23 
74M C11  C11  C 0 1 N N N 15.552 18.051 -4.932  5.534  -1.836 0.119  C11  74M 24 
74M C12  C12  C 0 1 N N N 15.359 19.297 -4.054  5.156  -2.936 -0.874 C12  74M 25 
74M C13  C13  C 0 1 N N N 16.240 20.474 -4.498  6.348  -3.873 -1.076 C13  74M 26 
74M C10  C10  C 0 1 N N N 14.112 18.628 -6.856  4.495  0.112  1.151  C10  74M 27 
74M O2   O2   O 0 1 N N N 14.886 18.668 -7.824  5.533  0.314  1.745  O2   74M 28 
74M H2   H2   H 0 1 N N N 12.977 18.266 -8.599  2.554  0.683  2.041  H2   74M 29 
74M H3   H3   H 0 1 N N N 11.964 20.690 -6.985  3.423  1.780  -0.776 H3   74M 30 
74M HN1  HN1  H 0 1 N N N 9.619  19.514 -6.089  0.865  0.280  -0.399 HN1  74M 31 
74M H5   H5   H 0 1 N N N 8.258  17.662 -7.797  -1.131 2.371  0.193  H5   74M 32 
74M H14  H14  H 0 1 N N N 6.231  18.534 -6.334  -2.346 1.483  -1.958 H14  74M 33 
74M H161 1H16 H 0 0 N N N 7.935  20.454 -5.514  -0.672 0.878  -3.749 H161 74M 34 
74M H162 2H16 H 0 0 N N N 8.192  19.187 -4.190  0.568  0.751  -2.479 H162 74M 35 
74M H151 1H15 H 0 0 N N N 6.794  16.860 -4.635  0.144  3.222  -2.243 H151 74M 36 
74M H152 2H15 H 0 0 N N N 8.553  17.189 -4.797  -1.304 3.253  -3.278 H152 74M 37 
74M H153 3H15 H 0 0 N N N 7.674  16.334 -6.110  -1.409 3.791  -1.585 H153 74M 38 
74M H171 1H17 H 0 0 N N N 5.441  19.403 -4.373  -0.559 -1.448 -3.127 H171 74M 39 
74M H172 2H17 H 0 0 N N N 5.973  21.092 -4.676  -0.611 -1.050 -1.393 H172 74M 40 
74M H173 3H17 H 0 0 N N N 6.476  20.248 -3.172  -2.052 -0.800 -2.406 H173 74M 41 
74M H7   H7   H 0 1 N N N 5.431  20.858 -9.963  -3.436 -0.701 2.178  H7   74M 42 
74M H201 1H20 H 0 0 N N N 5.220  19.468 -11.953 -5.701 -0.147 2.241  H201 74M 43 
74M H202 2H20 H 0 0 N N N 3.714  18.969 -11.162 -5.880 -0.311 0.463  H202 74M 44 
74M H191 1H19 H 0 0 N N N 5.653  17.128 -11.819 -4.709 2.042  2.052  H191 74M 45 
74M H192 2H19 H 0 0 N N N 4.606  16.919 -10.416 -5.878 2.087  0.691  H192 74M 46 
74M H181 1H18 H 0 0 N N N 6.605  16.933 -9.167  -3.257 2.528  0.189  H181 74M 47 
74M H182 2H18 H 0 0 N N N 7.514  17.662 -10.482 -4.199 1.486  -0.922 H182 74M 48 
74M H91  1H9  H 0 1 N N N 2.337  19.043 -6.899  -5.032 -4.019 -0.709 H91  74M 49 
74M H92  2H9  H 0 1 N N N 2.692  20.791 -7.118  -3.473 -4.490 0.011  H92  74M 50 
74M H93  3H9  H 0 1 N N N 3.330  19.917 -5.684  -4.996 -4.921 0.826  H93  74M 51 
74M HN3  HN3  H 0 1 N N N 13.768 17.082 -5.617  3.562  -1.101 -0.163 HN3  74M 52 
74M H111 1H11 H 0 0 N N N 16.446 18.194 -5.557  5.808  -2.286 1.073  H111 74M 53 
74M H112 2H11 H 0 0 N N N 15.672 17.170 -4.284  6.379  -1.269 -0.271 H112 74M 54 
74M H121 1H12 H 0 0 N N N 15.648 19.031 -3.027  4.882  -2.486 -1.829 H121 74M 55 
74M H122 2H12 H 0 0 N N N 14.306 19.608 -4.117  4.310  -3.503 -0.484 H122 74M 56 
74M H131 1H13 H 0 0 N N N 15.714 21.054 -5.271  7.193  -3.307 -1.467 H131 74M 57 
74M H132 2H13 H 0 0 N N N 17.186 20.090 -4.907  6.622  -4.324 -0.122 H132 74M 58 
74M H133 3H13 H 0 0 N N N 16.451 21.121 -3.634  6.078  -4.657 -1.784 H133 74M 59 
# 
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 
74M C2  O1   SING N N 1  
74M C2  C3   SING N N 2  
74M C2  C10  SING N N 3  
74M C2  H2   SING N N 4  
74M O1  C3   SING N N 5  
74M C3  C4   SING N N 6  
74M C3  H3   SING N N 7  
74M C4  O4   DOUB N N 8  
74M C4  N1   SING N N 9  
74M N1  C5   SING N N 10 
74M N1  HN1  SING N N 11 
74M C5  C6   SING N N 12 
74M C5  C14  SING N N 13 
74M C5  H5   SING N N 14 
74M C6  O5   DOUB N N 15 
74M C6  N2   SING N N 16 
74M C14 C16  SING N N 17 
74M C14 C15  SING N N 18 
74M C14 H14  SING N N 19 
74M C16 C17  SING N N 20 
74M C16 H161 SING N N 21 
74M C16 H162 SING N N 22 
74M C15 H151 SING N N 23 
74M C15 H152 SING N N 24 
74M C15 H153 SING N N 25 
74M C17 H171 SING N N 26 
74M C17 H172 SING N N 27 
74M C17 H173 SING N N 28 
74M N2  C7   SING N N 29 
74M N2  C18  SING N N 30 
74M C7  C8   SING N N 31 
74M C7  C20  SING N N 32 
74M C7  H7   SING N N 33 
74M C8  O6   DOUB N N 34 
74M C8  O7   SING N N 35 
74M C20 C19  SING N N 36 
74M C20 H201 SING N N 37 
74M C20 H202 SING N N 38 
74M C19 C18  SING N N 39 
74M C19 H191 SING N N 40 
74M C19 H192 SING N N 41 
74M C18 H181 SING N N 42 
74M C18 H182 SING N N 43 
74M O7  C9   SING N N 44 
74M C9  H91  SING N N 45 
74M C9  H92  SING N N 46 
74M C9  H93  SING N N 47 
74M N3  C11  SING N N 48 
74M N3  C10  SING N N 49 
74M N3  HN3  SING N N 50 
74M C11 C12  SING N N 51 
74M C11 H111 SING N N 52 
74M C11 H112 SING N N 53 
74M C12 C13  SING N N 54 
74M C12 H121 SING N N 55 
74M C12 H122 SING N N 56 
74M C13 H131 SING N N 57 
74M C13 H132 SING N N 58 
74M C13 H133 SING N N 59 
74M C10 O2   DOUB N N 60 
# 
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 
74M SMILES           ACDLabs              10.04 O=C(NCCC)C2OC2C(=O)NC(C(=O)N1C(C(=O)OC)CCC1)C(C)CC                                                                                                                                
74M InChI            InChI                1.02b InChI=1/C19H31N3O6/c1-5-9-20-16(23)14-15(28-14)17(24)21-13(11(3)6-2)18(25)22-10-7-8-12(22)19(26)27-4/h11-15H,5-10H2,1-4H3,(H,20,23)(H,21,24)/t11-,12-,13-,14-,15-/m0/s1/f/h20-21H 
74M InChIKey         InChI                1.02b XGWSRLSPWIEMLQ-XMFHWWKADE                                                                                                                                                         
74M SMILES_CANONICAL CACTVS               3.341 CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@H]2C(=O)OC                                                                                                           
74M SMILES           CACTVS               3.341 CCCNC(=O)[CH]1O[CH]1C(=O)N[CH]([CH](C)CC)C(=O)N2CCC[CH]2C(=O)OC                                                                                                                   
74M SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCNC(=O)[C@@H]1[C@H](O1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@H]2C(=O)OC                                                                                                         
74M SMILES           "OpenEye OEToolkits" 1.5.0 CCCNC(=O)C1C(O1)C(=O)NC(C(C)CC)C(=O)N2CCCC2C(=O)OC                                                                                                                                
# 
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 
74M "SYSTEMATIC NAME" ACDLabs              10.04 "methyl N-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]carbonyl}-L-isoleucyl-L-prolinate"                                          
74M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (2S)-1-[(2S,3S)-3-methyl-2-[[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]carbonylamino]pentanoyl]pyrrolidine-2-carboxylate" 
# 
