data_MEL
# 
_chem_comp.id                                    MEL 
_chem_comp.name                                  "[((1R)-2-{(2S)-2-[({4-[AMINO(IMINO)METHYL]BENZYL}AMINO)CARBONYL]AZETIDINYL}-1-CYCLOHEXYL-2-OXOETHYL)AMINO]ACETIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H31 N5 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MELAGATRAN (ASTRA-ZENECA)" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-10-23 
_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                        429.513 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MEL 
_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        1K1P 
_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 
MEL C1   C1   C 0 1 N N N 40.262 24.976 55.833 1.117  0.089  -4.568 C1   MEL 1  
MEL C2   C2   C 0 1 N N N 39.084 25.912 55.382 2.281  0.894  -3.987 C2   MEL 2  
MEL C3   C3   C 0 1 N N N 37.731 25.353 55.925 3.512  0.727  -4.880 C3   MEL 3  
MEL C4   C4   C 0 1 N N N 37.778 25.294 57.464 3.898  -0.751 -4.947 C4   MEL 4  
MEL C5   C5   C 0 1 N N N 38.962 24.407 57.916 2.734  -1.556 -5.527 C5   MEL 5  
MEL C6   C6   C 0 1 N N N 40.305 24.961 57.384 1.503  -1.389 -4.634 C6   MEL 6  
MEL N7   N7   N 0 1 N N N 42.758 25.096 56.050 -1.267 -0.398 -4.304 N7   MEL 7  
MEL C8   C8   C 0 1 N N R 41.612 25.292 55.112 -0.113 0.255  -3.674 C8   MEL 8  
MEL C9   C9   C 0 1 N N N 41.749 24.467 53.841 0.151  -0.375 -2.332 C9   MEL 9  
MEL O0   O0   O 0 1 N N N 42.338 23.411 53.862 -0.045 -1.561 -2.170 O0   MEL 10 
MEL N11  N11  N 0 1 N N N 41.059 24.876 52.778 0.605  0.377  -1.311 N11  MEL 11 
MEL C12  C12  C 0 1 N N S 41.367 24.357 51.397 0.889  0.127  0.115  C12  MEL 12 
MEL C13  C13  C 0 1 N N N 42.826 23.870 51.185 -0.286 0.381  1.022  C13  MEL 13 
MEL O14  O14  O 0 1 N N N 43.743 24.685 51.390 -1.352 0.720  0.552  O14  MEL 14 
MEL N15  N15  N 0 1 N N N 43.053 22.632 50.729 -0.154 0.231  2.355  N15  MEL 15 
MEL C16  C16  C 0 1 N N N 44.426 22.159 50.474 -1.298 0.478  3.236  C16  MEL 16 
MEL C17  C17  C 0 1 Y N N 44.795 21.040 51.428 -0.889 0.242  4.667  C17  MEL 17 
MEL C18  C18  C 0 1 Y N N 45.083 21.360 52.765 -0.379 1.286  5.419  C18  MEL 18 
MEL C19  C19  C 0 1 Y N N 45.433 20.336 53.671 -0.003 1.076  6.730  C19  MEL 19 
MEL C20  C20  C 0 1 Y N N 45.505 18.990 53.247 -0.139 -0.190 7.297  C20  MEL 20 
MEL C21  C21  C 0 1 Y N N 45.237 18.675 51.907 -0.648 -1.239 6.532  C21  MEL 21 
MEL C22  C22  C 0 1 Y N N 44.883 19.692 51.011 -1.026 -1.016 5.224  C22  MEL 22 
MEL C23  C23  C 0 1 N N N 45.874 17.902 54.214 0.262  -0.422 8.703  C23  MEL 23 
MEL N24  N24  N 0 1 N N N 46.657 18.178 55.214 0.742  0.557  9.414  N24  MEL 24 
MEL N25  N25  N 0 1 N N N 45.405 16.684 54.025 0.127  -1.675 9.261  N25  MEL 25 
MEL C26  C26  C 0 1 N N N 41.045 25.745 50.820 1.869  1.311  0.023  C26  MEL 26 
MEL C27  C27  C 0 1 N N N 41.271 26.258 52.274 1.022  1.789  -1.170 C27  MEL 27 
MEL C28  C28  C 0 1 N N N 44.094 25.528 55.573 -1.850 0.577  -5.235 C28  MEL 28 
MEL C29  C29  C 0 1 N N N 45.212 25.106 56.478 -3.116 0.013  -5.827 C29  MEL 29 
MEL O30  O30  O 0 1 N N N 45.027 25.142 57.702 -3.824 0.735  -6.710 O30  MEL 30 
MEL O31  O31  O 0 1 N N N 46.305 24.740 55.975 -3.494 -1.088 -5.506 O31  MEL 31 
MEL H11  1H1  H 0 1 N N N 40.074 23.929 55.500 0.890  0.451  -5.571 H11  MEL 32 
MEL H21  1H2  H 0 1 N N N 39.064 26.060 54.277 2.007  1.948  -3.940 H21  MEL 33 
MEL H22  2H2  H 0 1 N N N 39.251 26.973 55.683 2.508  0.532  -2.984 H22  MEL 34 
MEL H31  1H3  H 0 1 N N N 37.472 24.367 55.474 3.285  1.089  -5.883 H31  MEL 35 
MEL H32  2H3  H 0 1 N N N 36.856 25.935 55.553 4.342  1.301  -4.467 H32  MEL 36 
MEL H41  1H4  H 0 1 N N N 36.810 24.956 57.901 4.775  -0.869 -5.583 H41  MEL 37 
MEL H42  2H4  H 0 1 N N N 37.816 26.310 57.922 4.125  -1.112 -3.944 H42  MEL 38 
MEL H51  1H5  H 0 1 N N N 38.812 23.341 57.624 2.506  -1.194 -6.530 H51  MEL 39 
MEL H52  2H5  H 0 1 N N N 38.980 24.278 59.023 3.008  -2.610 -5.575 H52  MEL 40 
MEL H61  1H6  H 0 1 N N N 40.553 25.960 57.813 1.730  -1.751 -3.631 H61  MEL 41 
MEL H62  2H6  H 0 1 N N N 41.184 24.400 57.780 0.673  -1.963 -5.048 H62  MEL 42 
MEL H71  1H7  H 0 1 N N N 42.799 24.119 56.340 -0.902 -1.152 -4.866 H71  MEL 43 
MEL H81  1H8  H 0 1 N N N 41.620 26.363 54.802 -0.325 1.316  -3.542 H81  MEL 44 
MEL H121 1H12 H 0 0 N N N 40.855 23.448 51.003 1.374  -0.829 0.305  H121 MEL 45 
MEL H151 1H15 H 0 0 N N N 42.214 22.072 50.582 0.697  -0.039 2.730  H151 MEL 46 
MEL H161 1H16 H 0 0 N N N 45.164 22.994 50.512 -2.111 -0.198 2.974  H161 MEL 47 
MEL H162 2H16 H 0 0 N N N 44.568 21.858 49.410 -1.631 1.509  3.119  H162 MEL 48 
MEL H181 1H18 H 0 0 N N N 45.035 22.409 53.102 -0.275 2.266  4.979  H181 MEL 49 
MEL H191 1H19 H 0 0 N N N 45.653 20.590 54.722 0.394  1.891  7.316  H191 MEL 50 
MEL H211 1H21 H 0 0 N N N 45.304 17.631 51.559 -0.755 -2.223 6.966  H211 MEL 51 
MEL H221 1H22 H 0 0 N N N 44.670 19.427 49.962 -1.424 -1.827 4.632  H221 MEL 52 
MEL H241 1H24 H 0 0 N N N 47.152 17.754 54.429 0.837  1.439  9.021  H241 MEL 53 
MEL H251 1H25 H 0 0 N N N 45.652 16.381 53.083 0.390  -1.827 10.182 H251 MEL 54 
MEL H252 2H25 H 0 0 N N N 45.656 15.945 54.682 -0.234 -2.404 8.733  H252 MEL 55 
MEL H261 1H26 H 0 0 N N N 40.104 25.950 50.259 1.831  1.980  0.883  H261 MEL 56 
MEL H262 2H26 H 0 0 N N N 41.599 26.168 49.949 2.884  1.021  -0.247 H262 MEL 57 
MEL H271 1H27 H 0 0 N N N 42.201 26.815 52.535 0.210  2.461  -0.892 H271 MEL 58 
MEL H272 2H27 H 0 0 N N N 40.661 27.102 52.673 1.614  2.159  -2.008 H272 MEL 59 
MEL H281 1H28 H 0 0 N N N 44.117 26.630 55.403 -2.078 1.498  -4.699 H281 MEL 60 
MEL H282 2H28 H 0 0 N N N 44.275 25.177 54.530 -1.139 0.788  -6.033 H282 MEL 61 
MEL H301 1H30 H 0 0 N N N 45.736 24.875 58.276 -4.636 0.373  -7.089 H301 MEL 62 
# 
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 
MEL C1  C2   SING N N 1  
MEL C1  C6   SING N N 2  
MEL C1  C8   SING N N 3  
MEL C1  H11  SING N N 4  
MEL C2  C3   SING N N 5  
MEL C2  H21  SING N N 6  
MEL C2  H22  SING N N 7  
MEL C3  C4   SING N N 8  
MEL C3  H31  SING N N 9  
MEL C3  H32  SING N N 10 
MEL C4  C5   SING N N 11 
MEL C4  H41  SING N N 12 
MEL C4  H42  SING N N 13 
MEL C5  C6   SING N N 14 
MEL C5  H51  SING N N 15 
MEL C5  H52  SING N N 16 
MEL C6  H61  SING N N 17 
MEL C6  H62  SING N N 18 
MEL N7  C8   SING N N 19 
MEL N7  C28  SING N N 20 
MEL N7  H71  SING N N 21 
MEL C8  C9   SING N N 22 
MEL C8  H81  SING N N 23 
MEL C9  O0   DOUB N N 24 
MEL C9  N11  SING N N 25 
MEL N11 C12  SING N N 26 
MEL N11 C27  SING N N 27 
MEL C12 C13  SING N N 28 
MEL C12 C26  SING N N 29 
MEL C12 H121 SING N N 30 
MEL C13 O14  DOUB N N 31 
MEL C13 N15  SING N N 32 
MEL N15 C16  SING N N 33 
MEL N15 H151 SING N N 34 
MEL C16 C17  SING N N 35 
MEL C16 H161 SING N N 36 
MEL C16 H162 SING N N 37 
MEL C17 C18  DOUB Y N 38 
MEL C17 C22  SING Y N 39 
MEL C18 C19  SING Y N 40 
MEL C18 H181 SING N N 41 
MEL C19 C20  DOUB Y N 42 
MEL C19 H191 SING N N 43 
MEL C20 C21  SING Y N 44 
MEL C20 C23  SING N N 45 
MEL C21 C22  DOUB Y N 46 
MEL C21 H211 SING N N 47 
MEL C22 H221 SING N N 48 
MEL C23 N24  DOUB N N 49 
MEL C23 N25  SING N N 50 
MEL N24 H241 SING N N 51 
MEL N25 H251 SING N N 52 
MEL N25 H252 SING N N 53 
MEL C26 C27  SING N N 54 
MEL C26 H261 SING N N 55 
MEL C26 H262 SING N N 56 
MEL C27 H271 SING N N 57 
MEL C27 H272 SING N N 58 
MEL C28 C29  SING N N 59 
MEL C28 H281 SING N N 60 
MEL C28 H282 SING N N 61 
MEL C29 O30  SING N N 62 
MEL C29 O31  DOUB N N 63 
MEL O30 H301 SING N N 64 
# 
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 
MEL SMILES           ACDLabs              10.04 O=C(NCc1ccc(C(=[N@H])N)cc1)C3N(C(=O)C(NCC(=O)O)C2CCCCC2)CC3                                                                                                                                                  
MEL InChI            InChI                1.02b InChI=1/C22H31N5O4/c23-20(24)16-8-6-14(7-9-16)12-26-21(30)17-10-11-27(17)22(31)19(25-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,25H,1-5,10-13H2,(H3,23,24)(H,26,30)(H,28,29)/t17-,19+/m0/s1/f/h23,26,28H,24H2 
MEL InChIKey         InChI                1.02b DKWNMCUOEDMMIN-USDBNRLDDK                                                                                                                                                                                    
MEL SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[C@@H]2CCN2C(=O)[C@H](NCC(O)=O)C3CCCCC3)cc1                                                                                                                                               
MEL SMILES           CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[CH]2CCN2C(=O)[CH](NCC(O)=O)C3CCCCC3)cc1                                                                                                                                                  
MEL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CNC(=O)[C@@H]2CCN2C(=O)[C@@H](C3CCCCC3)NCC(=O)O)C(=N)N                                                                                                                                              
MEL SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CNC(=O)C2CCN2C(=O)C(C3CCCCC3)NCC(=O)O)C(=N)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 
MEL "SYSTEMATIC NAME" ACDLabs              10.04 N-[(1R)-2-{(2S)-2-[(4-carbamimidoylbenzyl)carbamoyl]azetidin-1-yl}-1-cyclohexyl-2-oxoethyl]glycine                       
MEL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[(1R)-2-[(2S)-2-[(4-carbamimidoylphenyl)methylcarbamoyl]azetidin-1-yl]-1-cyclohexyl-2-oxo-ethyl]amino]ethanoic acid" 
# 
