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                    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                        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 InChI            InChI                1.02b 
InChI=1/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/f/h26H 
15M InChIKey         InChI                1.02b AQOKCDNYWBIDND-FQMNGLPRDN 
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 
# 
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    
# 
