data_15M # _chem_comp.id 15M _chem_comp.name "(5Z)-7-{(1R,2R,3R,5S)-3,5-DIHYDROXY-2-[(1E,3S)-3-HYDROXY-5-PHENYLPENT-1-ENYL]CYCLOPENTYL}-N-ETHYLHEPT-5-ENAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H37 N O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms BIMATOPROST _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-12-07 _chem_comp.pdbx_modified_date 2020-06-17 _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 415.566 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 15M _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 2F38 _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 15M C1 C1 C 0 1 N N N 25.446 -11.684 37.454 5.812 2.430 0.054 C1 15M 1 15M C2 C2 C 0 1 N N N 24.088 -11.116 37.941 4.548 1.718 -0.357 C2 15M 2 15M C3 C3 C 0 1 N N N 22.959 -12.097 37.567 4.844 0.231 -0.562 C3 15M 3 15M C4 C4 C 0 1 N N N 21.558 -11.450 37.729 3.562 -0.492 -0.979 C4 15M 4 15M C5 C5 C 0 1 N N N 21.191 -11.160 39.160 3.853 -1.957 -1.180 C5 15M 5 15M C6 C6 C 0 1 N N N 20.785 -12.102 40.067 3.125 -2.859 -0.571 C6 15M 6 15M C7 C7 C 0 1 N N N 20.668 -13.573 39.742 1.893 -2.444 0.192 C7 15M 7 15M C8 C8 C 0 1 N N R 19.239 -14.207 39.877 0.691 -3.251 -0.302 C8 15M 8 15M C9 C9 C 0 1 N N S 18.708 -14.408 41.322 0.859 -4.733 0.076 C9 15M 9 15M C10 C10 C 0 1 N N N 17.281 -13.829 41.365 -0.330 -5.093 0.989 C10 15M 10 15M C11 C11 C 0 1 N N R 16.855 -13.587 39.914 -1.419 -4.054 0.622 C11 15M 11 15M C12 C12 C 0 1 N N R 18.153 -13.416 39.118 -0.596 -2.761 0.394 C12 15M 12 15M C13 C13 C 0 1 N N N 18.000 -13.960 37.753 -1.350 -1.805 -0.494 C13 15M 13 15M C14 C14 C 0 1 N N N 17.830 -13.138 36.718 -1.643 -0.603 -0.063 C14 15M 14 15M C15 C15 C 0 1 N N S 17.664 -13.698 35.352 -2.397 0.352 -0.951 C15 15M 15 15M C16 C16 C 0 1 N N N 18.632 -13.002 34.391 -3.649 0.845 -0.222 C16 15M 16 15M C17 C17 C 0 1 N N N 20.069 -13.548 34.571 -4.348 1.908 -1.072 C17 15M 17 15M C18 C18 C 0 1 Y N N 20.947 -13.043 33.466 -5.582 2.394 -0.355 C18 15M 18 15M C19 C19 C 0 1 Y N N 21.402 -11.689 33.466 -6.795 1.767 -0.566 C19 15M 19 15M C20 C20 C 0 1 Y N N 22.227 -11.208 32.417 -7.926 2.209 0.096 C20 15M 20 15M C21 C21 C 0 1 Y N N 22.603 -12.086 31.350 -7.844 3.284 0.961 C21 15M 21 15M C22 C22 C 0 1 Y N N 22.156 -13.440 31.337 -6.632 3.914 1.168 C22 15M 22 15M C23 C23 C 0 1 Y N N 21.329 -13.920 32.398 -5.500 3.469 0.510 C23 15M 23 15M C24 C24 C 0 1 N N N 27.183 -14.395 36.672 6.723 5.935 0.894 C24 15M 24 15M C25 C25 C 0 1 N N N 27.165 -13.276 37.733 7.019 4.448 0.689 C25 15M 25 15M N N N 0 1 N N N 25.995 -12.736 38.107 5.791 3.756 0.290 N 15M 26 15M O1 O1 O 0 1 N N N 26.046 -11.145 36.420 6.847 1.809 0.171 O1 15M 27 15M O9 O9 O 0 1 N N N 19.494 -13.740 42.270 2.090 -4.923 0.776 O9 15M 28 15M O11 O11 O 0 1 N N N 16.089 -12.413 39.822 -2.343 -3.887 1.699 O11 15M 29 15M O15 O15 O 0 1 N N N 16.342 -13.489 34.899 -2.778 -0.316 -2.155 O15 15M 30 15M H21A 1H2 H 0 0 N N N 23.903 -10.143 37.462 3.796 1.835 0.422 H21A 15M 31 15M H22A 2H2 H 0 0 N N N 24.115 -10.986 39.033 4.177 2.146 -1.288 H22A 15M 32 15M H31 1H3 H 0 1 N N N 23.018 -12.963 38.243 5.597 0.114 -1.341 H31 15M 33 15M H32 2H3 H 0 1 N N N 23.088 -12.401 36.518 5.216 -0.197 0.369 H32 15M 34 15M H41 1H4 H 0 1 N N N 20.821 -12.170 37.344 2.809 -0.375 -0.199 H41 15M 35 15M H42 2H4 H 0 1 N N N 21.554 -10.500 37.175 3.190 -0.064 -1.910 H42 15M 36 15M H5 H5 H 0 1 N N N 21.252 -10.135 39.495 4.663 -2.262 -1.826 H5 15M 37 15M H6 H6 H 0 1 N N N 20.536 -11.777 41.066 3.406 -3.901 -0.616 H6 15M 38 15M H71 1H7 H 0 1 N N N 21.293 -14.091 40.485 2.045 -2.631 1.255 H71 15M 39 15M H72 2H7 H 0 1 N N N 20.983 -13.701 38.696 1.708 -1.382 0.033 H72 15M 40 15M H8 H8 H 0 1 N N N 19.409 -15.199 39.433 0.592 -3.150 -1.383 H8 15M 41 15M H9 H9 H 0 1 N N N 18.733 -15.480 41.569 0.842 -5.351 -0.822 H9 15M 42 15M H101 1H10 H 0 0 N N N 17.254 -12.894 41.943 -0.681 -6.103 0.778 H101 15M 43 15M H102 2H10 H 0 0 N N N 16.595 -14.538 41.852 -0.049 -4.997 2.038 H102 15M 44 15M H11 H11 H 0 1 N N N 16.244 -14.418 39.532 -1.939 -4.346 -0.290 H11 15M 45 15M H12 H12 H 0 1 N N N 18.418 -12.352 39.024 -0.357 -2.288 1.347 H12 15M 46 15M H13 H13 H 0 1 N N N 18.026 -15.028 37.593 -1.649 -2.111 -1.485 H13 15M 47 15M H14 H14 H 0 1 N N N 17.813 -12.069 36.872 -1.344 -0.298 0.929 H14 15M 48 15M H15 H15 H 0 1 N N N 17.875 -14.777 35.384 -1.760 1.203 -1.193 H15 15M 49 15M H161 1H16 H 0 0 N N N 18.633 -11.924 34.608 -4.328 0.007 -0.059 H161 15M 50 15M H162 2H16 H 0 0 N N N 18.305 -13.185 33.357 -3.366 1.276 0.738 H162 15M 51 15M H171 1H17 H 0 0 N N N 20.046 -14.647 34.543 -3.670 2.746 -1.236 H171 15M 52 15M H172 2H17 H 0 0 N N N 20.469 -13.209 35.538 -4.632 1.478 -2.032 H172 15M 53 15M H19 H19 H 0 1 N N N 21.116 -11.027 34.270 -6.859 0.927 -1.242 H19 15M 54 15M H20 H20 H 0 1 N N N 22.570 -10.184 32.423 -8.873 1.716 -0.066 H20 15M 55 15M H21 H21 H 0 1 N N N 23.229 -11.720 30.550 -8.728 3.631 1.476 H21 15M 56 15M H22 H22 H 0 1 N N N 22.441 -14.099 30.530 -6.568 4.754 1.844 H22 15M 57 15M H23 H23 H 0 1 N N N 20.991 -14.946 32.396 -4.553 3.962 0.672 H23 15M 58 15M H241 1H24 H 0 0 N N N 26.289 -15.025 36.789 7.637 6.450 1.191 H241 15M 59 15M H242 2H24 H 0 0 N N N 28.085 -15.010 36.803 6.352 6.363 -0.037 H242 15M 60 15M H243 3H24 H 0 0 N N N 27.187 -13.948 35.667 5.970 6.052 1.673 H243 15M 61 15M H251 1H25 H 0 0 N N N 27.696 -12.444 37.248 7.772 4.331 -0.090 H251 15M 62 15M H252 2H25 H 0 0 N N N 27.609 -13.707 38.642 7.391 4.020 1.620 H252 15M 63 15M HN HN H 0 1 N N N 25.513 -13.123 38.893 4.963 4.253 0.196 HN 15M 64 15M HO9 HO9 H 0 1 N N N 20.361 -13.589 41.913 2.148 -5.864 0.990 HO9 15M 65 15M H1 H1 H 0 1 N N N 15.916 -12.078 40.694 -2.764 -4.746 1.842 H1 15M 66 15M H2 H2 H 0 1 N N N 15.755 -13.442 35.644 -3.340 -1.060 -1.896 H2 15M 67 # # 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 15M C1 C2 SING N N 1 15M C1 N SING N N 2 15M C1 O1 DOUB N N 3 15M C2 C3 SING N N 4 15M C2 H21A SING N N 5 15M C2 H22A SING N N 6 15M C3 C4 SING N N 7 15M C3 H31 SING N N 8 15M C3 H32 SING N N 9 15M C4 C5 SING N N 10 15M C4 H41 SING N N 11 15M C4 H42 SING N N 12 15M C5 C6 DOUB N Z 13 15M C5 H5 SING N N 14 15M C6 C7 SING N N 15 15M C6 H6 SING N N 16 15M C7 C8 SING N N 17 15M C7 H71 SING N N 18 15M C7 H72 SING N N 19 15M C8 C9 SING N N 20 15M C8 C12 SING N N 21 15M C8 H8 SING N N 22 15M C9 C10 SING N N 23 15M C9 O9 SING N N 24 15M C9 H9 SING N N 25 15M C10 C11 SING N N 26 15M C10 H101 SING N N 27 15M C10 H102 SING N N 28 15M C11 C12 SING N N 29 15M C11 O11 SING N N 30 15M C11 H11 SING N N 31 15M C12 C13 SING N N 32 15M C12 H12 SING N N 33 15M C13 C14 DOUB N E 34 15M C13 H13 SING N N 35 15M C14 C15 SING N N 36 15M C14 H14 SING N N 37 15M C15 C16 SING N N 38 15M C15 O15 SING N N 39 15M C15 H15 SING N N 40 15M C16 C17 SING N N 41 15M C16 H161 SING N N 42 15M C16 H162 SING N N 43 15M C17 C18 SING N N 44 15M C17 H171 SING N N 45 15M C17 H172 SING N N 46 15M C18 C19 SING Y N 47 15M C18 C23 DOUB Y N 48 15M C19 C20 DOUB Y N 49 15M C19 H19 SING N N 50 15M C20 C21 SING Y N 51 15M C20 H20 SING N N 52 15M C21 C22 DOUB Y N 53 15M C21 H21 SING N N 54 15M C22 C23 SING Y N 55 15M C22 H22 SING N N 56 15M C23 H23 SING N N 57 15M C24 C25 SING N N 58 15M C24 H241 SING N N 59 15M C24 H242 SING N N 60 15M C24 H243 SING N N 61 15M C25 N SING N N 62 15M C25 H251 SING N N 63 15M C25 H252 SING N N 64 15M N HN SING N N 65 15M O9 HO9 SING N N 66 15M O11 H1 SING N N 67 15M O15 H2 SING N N 68 # # 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 15M SMILES ACDLabs 10.04 "O=C(NCC)CCC/C=C\CC2C(/C=C/C(O)CCc1ccccc1)C(O)CC2O" 15M SMILES_CANONICAL CACTVS 3.341 "CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCc2ccccc2" 15M SMILES CACTVS 3.341 "CCNC(=O)CCCC=CC[CH]1[CH](O)C[CH](O)[CH]1C=C[CH](O)CCc2ccccc2" 15M SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CCNC(=O)CCC\C=C/C[C@H]1[C@H](C[C@H]([C@@H]1\C=C\[C@H](CCc2ccccc2)O)O)O" 15M SMILES "OpenEye OEToolkits" 1.5.0 "CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCc2ccccc2)O)O)O" 15M InChI InChI 1.03 "InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1" 15M InChIKey InChI 1.03 AQOKCDNYWBIDND-FTOWTWDKSA-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 15M "SYSTEMATIC NAME" ACDLabs 10.04 "(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide" 15M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-pent-1-enyl]cyclopentyl]-N-ethyl-hept-5-enamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 15M "Create component" 2005-12-07 RCSB 15M "Modify descriptor" 2011-06-04 RCSB 15M "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 15M _pdbx_chem_comp_synonyms.name BIMATOPROST _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##