data_XMA # _chem_comp.id XMA _chem_comp.name "(-)-7-[(6-CHLORO-2-NAPHTHALENYL)SULFONYL]TETRAHYDRO-8A-(METHOXYMETHYL)-1'-(4-PYRIDINYL)-SPIRO[5H-OXAZOLO[3,2-A]PYRAZINE-2(3H),4'-PIPERIDIN]-5-ONE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H29 Cl N4 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2001-03-12 _chem_comp.pdbx_modified_date 2011-06-04 _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 557.061 _chem_comp.one_letter_code ? _chem_comp.three_letter_code XMA _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 1IOE _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 XMA C1 C1 C 0 1 Y N N 8.347 25.084 7.850 0.761 0.101 4.192 C1 XMA 1 XMA C2 C2 C 0 1 Y N N 8.940 23.806 7.493 0.674 -0.839 3.212 C2 XMA 2 XMA C3 C3 C 0 1 Y N N 8.431 24.412 10.366 -1.379 -0.664 5.068 C3 XMA 3 XMA C4 C4 C 0 1 Y N N 9.031 23.115 9.984 -1.430 -1.627 4.045 C4 XMA 4 XMA C5 C5 C 0 1 Y N N 9.279 22.822 8.589 -0.417 -1.703 3.141 C5 XMA 5 XMA C6 C6 C 0 1 Y N N 8.075 25.442 9.233 -0.269 0.213 5.141 C6 XMA 6 XMA CL7 CL7 CL 0 0 N N N 7.259 26.541 13.705 -3.593 0.518 8.173 CL7 XMA 7 XMA C8 C8 C 0 1 Y N N 7.481 26.746 9.597 -0.216 1.175 6.164 C8 XMA 8 XMA C9 C9 C 0 1 Y N N 8.158 24.791 11.742 -2.406 -0.556 6.021 C9 XMA 9 XMA C10 C10 C 0 1 Y N N 7.242 27.050 10.975 -1.230 1.252 7.069 C10 XMA 10 XMA C11 C11 C 0 1 Y N N 7.573 26.091 12.048 -2.322 0.388 6.998 C11 XMA 11 XMA S12 S12 S 0 1 N N N 9.120 23.426 5.810 1.965 -0.972 2.020 S12 XMA 12 XMA O13 O13 O 0 1 N N N 9.193 24.764 5.019 1.819 -2.258 1.435 O13 XMA 13 XMA O14 O14 O 0 1 N N N 10.368 22.556 5.571 3.136 -0.489 2.663 O14 XMA 14 XMA C15 C15 C 0 1 N N N 5.300 22.327 4.361 2.333 2.117 -0.401 C15 XMA 15 XMA O16 O16 O 0 1 N N N 4.254 22.834 3.963 2.749 3.255 -0.469 O16 XMA 16 XMA C17 C17 C 0 1 N N N 6.475 23.271 4.804 2.081 1.496 0.947 C17 XMA 17 XMA N18 N18 N 0 1 N N N 7.735 22.631 5.272 1.636 0.111 0.811 N18 XMA 18 XMA C19 C19 C 0 1 N N S 6.819 20.292 4.965 1.749 0.001 -1.610 C19 XMA 19 XMA C20 C20 C 0 1 N N N 7.864 19.816 3.874 3.017 -0.855 -1.624 C20 XMA 20 XMA O21 O21 O 0 1 N N N 7.347 18.852 2.915 2.658 -2.237 -1.668 O21 XMA 21 XMA C22 C22 C 0 1 N N N 8.220 17.899 2.470 3.878 -2.981 -1.659 C22 XMA 22 XMA C23 C23 C 0 1 N N N 7.586 21.310 5.916 0.902 -0.335 -0.378 C23 XMA 23 XMA N24 N24 N 0 1 N N N 5.539 20.911 4.467 2.105 1.430 -1.521 N24 XMA 24 XMA C25 C25 C 0 1 N N N 4.475 19.897 4.609 2.092 1.900 -2.920 C25 XMA 25 XMA C26 C26 C 0 1 Y N N 0.222 15.076 8.637 -4.405 -0.993 -5.681 C26 XMA 26 XMA N27 N27 N 0 1 N N N 2.477 17.858 7.102 -1.299 0.937 -5.352 N27 XMA 27 XMA C28 C28 C 0 1 Y N N 1.531 17.124 8.006 -2.358 0.222 -5.903 C28 XMA 28 XMA C29 C29 C 0 1 Y N N 1.131 15.722 7.744 -3.369 -0.296 -5.095 C29 XMA 29 XMA C30 C30 C 0 1 N N N 2.885 19.326 7.388 -0.089 0.139 -5.579 C30 XMA 30 XMA C31 C31 C 0 1 Y N N 0.944 17.763 9.209 -2.433 0.001 -7.279 C31 XMA 31 XMA C32 C32 C 0 1 N N N 3.084 17.181 5.841 -1.529 0.981 -3.904 C32 XMA 32 XMA C33 C33 C 0 1 N N N 4.977 19.019 5.803 0.927 1.067 -3.502 C33 XMA 33 XMA O34 O34 O 0 1 N N N 6.428 19.157 5.733 1.002 -0.211 -2.813 O34 XMA 34 XMA C35 C35 C 0 1 N N N 4.423 19.520 7.211 1.125 0.870 -5.001 C35 XMA 35 XMA N36 N36 N 0 1 Y N N -0.309 15.703 9.753 -4.440 -1.181 -6.988 N36 XMA 36 XMA C37 C37 C 0 1 Y N N 0.042 17.013 10.033 -3.499 -0.711 -7.786 C37 XMA 37 XMA C38 C38 C 0 1 N N N 4.616 17.485 5.699 -0.400 1.762 -3.226 C38 XMA 38 XMA H1 H1 H 0 1 N N N 8.102 25.787 7.067 1.615 0.760 4.237 H1 XMA 39 XMA H4 H4 H 0 1 N N N 9.283 22.390 10.743 -2.270 -2.302 3.977 H4 XMA 40 XMA H5 H5 H 0 1 N N N 9.719 21.872 8.323 -0.459 -2.443 2.356 H5 XMA 41 XMA H8 H8 H 0 1 N N N 7.230 27.463 8.830 0.622 1.851 6.230 H8 XMA 42 XMA H9 H9 H 0 1 N N N 8.390 24.105 12.543 -3.258 -1.218 5.977 H9 XMA 43 XMA H10 H10 H 0 1 N N N 6.809 28.004 11.236 -1.187 1.992 7.854 H10 XMA 44 XMA H171 1H17 H 0 0 N N N 6.089 23.813 5.680 1.313 2.070 1.467 H171 XMA 45 XMA H172 2H17 H 0 0 N N N 6.736 23.887 3.931 3.001 1.521 1.531 H172 XMA 46 XMA H201 1H20 H 0 0 N N N 8.677 19.312 4.418 3.615 -0.606 -2.501 H201 XMA 47 XMA H202 2H20 H 0 0 N N N 8.191 20.704 3.313 3.597 -0.659 -0.722 H202 XMA 48 XMA H221 1H22 H 0 0 N N N 7.763 16.904 2.578 3.653 -4.048 -1.653 H221 XMA 49 XMA H222 2H22 H 0 0 N N N 9.145 17.944 3.063 4.459 -2.738 -2.549 H222 XMA 50 XMA H223 3H22 H 0 0 N N N 8.455 18.082 1.411 4.452 -2.726 -0.769 H223 XMA 51 XMA H231 1H23 H 0 0 N N N 7.001 21.435 6.839 -0.055 0.183 -0.437 H231 XMA 52 XMA H232 2H23 H 0 0 N N N 8.585 20.907 6.138 0.736 -1.411 -0.327 H232 XMA 53 XMA H251 1H25 H 0 0 N N N 4.309 19.317 3.689 1.876 2.967 -2.974 H251 XMA 54 XMA H252 2H25 H 0 0 N N N 3.501 20.359 4.827 3.031 1.666 -3.422 H252 XMA 55 XMA H26 H26 H 0 1 N N N -0.064 14.055 8.434 -5.194 -1.395 -5.064 H26 XMA 56 XMA H29 H29 H 0 1 N N N 1.522 15.194 6.887 -3.346 -0.147 -4.026 H29 XMA 57 XMA H301 1H30 H 0 0 N N N 2.616 19.571 8.426 -0.196 -0.829 -5.091 H301 XMA 58 XMA H302 2H30 H 0 0 N N N 2.357 19.988 6.686 0.052 -0.007 -6.650 H302 XMA 59 XMA H31 H31 H 0 1 N N N 1.194 18.783 9.462 -1.668 0.384 -7.937 H31 XMA 60 XMA H321 1H32 H 0 0 N N N 2.570 17.582 4.955 -1.555 -0.034 -3.509 H321 XMA 61 XMA H322 2H32 H 0 0 N N N 2.946 16.093 5.924 -2.482 1.471 -3.703 H322 XMA 62 XMA H351 1H35 H 0 0 N N N 4.916 18.914 7.986 1.230 1.841 -5.485 H351 XMA 63 XMA H352 2H35 H 0 0 N N N 4.644 20.594 7.302 2.023 0.277 -5.175 H352 XMA 64 XMA H37 H37 H 0 1 N N N -0.380 17.488 10.906 -3.566 -0.886 -8.849 H37 XMA 65 XMA H381 1H38 H 0 0 N N N 4.918 17.151 4.696 -0.576 1.797 -2.151 H381 XMA 66 XMA H382 2H38 H 0 0 N N N 5.144 16.956 6.506 -0.370 2.777 -3.624 H382 XMA 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 XMA C1 C2 DOUB Y N 1 XMA C1 C6 SING Y N 2 XMA C1 H1 SING N N 3 XMA C2 C5 SING Y N 4 XMA C2 S12 SING N N 5 XMA C3 C4 SING Y N 6 XMA C3 C6 DOUB Y N 7 XMA C3 C9 SING Y N 8 XMA C4 C5 DOUB Y N 9 XMA C4 H4 SING N N 10 XMA C5 H5 SING N N 11 XMA C6 C8 SING Y N 12 XMA CL7 C11 SING N N 13 XMA C8 C10 DOUB Y N 14 XMA C8 H8 SING N N 15 XMA C9 C11 DOUB Y N 16 XMA C9 H9 SING N N 17 XMA C10 C11 SING Y N 18 XMA C10 H10 SING N N 19 XMA S12 O13 DOUB N N 20 XMA S12 O14 DOUB N N 21 XMA S12 N18 SING N N 22 XMA C15 O16 DOUB N N 23 XMA C15 C17 SING N N 24 XMA C15 N24 SING N N 25 XMA C17 N18 SING N N 26 XMA C17 H171 SING N N 27 XMA C17 H172 SING N N 28 XMA N18 C23 SING N N 29 XMA C19 C20 SING N N 30 XMA C19 C23 SING N N 31 XMA C19 N24 SING N N 32 XMA C19 O34 SING N N 33 XMA C20 O21 SING N N 34 XMA C20 H201 SING N N 35 XMA C20 H202 SING N N 36 XMA O21 C22 SING N N 37 XMA C22 H221 SING N N 38 XMA C22 H222 SING N N 39 XMA C22 H223 SING N N 40 XMA C23 H231 SING N N 41 XMA C23 H232 SING N N 42 XMA N24 C25 SING N N 43 XMA C25 C33 SING N N 44 XMA C25 H251 SING N N 45 XMA C25 H252 SING N N 46 XMA C26 C29 DOUB Y N 47 XMA C26 N36 SING Y N 48 XMA C26 H26 SING N N 49 XMA N27 C28 SING N N 50 XMA N27 C30 SING N N 51 XMA N27 C32 SING N N 52 XMA C28 C29 SING Y N 53 XMA C28 C31 DOUB Y N 54 XMA C29 H29 SING N N 55 XMA C30 C35 SING N N 56 XMA C30 H301 SING N N 57 XMA C30 H302 SING N N 58 XMA C31 C37 SING Y N 59 XMA C31 H31 SING N N 60 XMA C32 C38 SING N N 61 XMA C32 H321 SING N N 62 XMA C32 H322 SING N N 63 XMA C33 O34 SING N N 64 XMA C33 C35 SING N N 65 XMA C33 C38 SING N N 66 XMA C35 H351 SING N N 67 XMA C35 H352 SING N N 68 XMA N36 C37 DOUB Y N 69 XMA C37 H37 SING N N 70 XMA C38 H381 SING N N 71 XMA C38 H382 SING N N 72 # 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 XMA SMILES ACDLabs 10.04 "Clc2ccc1cc(ccc1c2)S(=O)(=O)N4CC(=O)N3CC6(OC3(COC)C4)CCN(c5ccncc5)CC6" XMA SMILES_CANONICAL CACTVS 3.341 "COC[C@@]12CN(CC(=O)N1CC3(CCN(CC3)c4ccncc4)O2)[S](=O)(=O)c5ccc6cc(Cl)ccc6c5" XMA SMILES CACTVS 3.341 "COC[C]12CN(CC(=O)N1CC3(CCN(CC3)c4ccncc4)O2)[S](=O)(=O)c5ccc6cc(Cl)ccc6c5" XMA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COC[C@@]12C[N@@](CC(=O)N1CC3(O2)CCN(CC3)c4ccncc4)S(=O)(=O)c5ccc6cc(ccc6c5)Cl" XMA SMILES "OpenEye OEToolkits" 1.5.0 "COCC12CN(CC(=O)N1CC3(O2)CCN(CC3)c4ccncc4)S(=O)(=O)c5ccc6cc(ccc6c5)Cl" XMA InChI InChI 1.03 "InChI=1S/C27H29ClN4O5S/c1-36-19-27-18-31(38(34,35)24-5-3-20-14-22(28)4-2-21(20)15-24)16-25(33)32(27)17-26(37-27)8-12-30(13-9-26)23-6-10-29-11-7-23/h2-7,10-11,14-15H,8-9,12-13,16-19H2,1H3/t27-/m0/s1" XMA InChIKey InChI 1.03 OCCGRNQFQCNISA-MHZLTWQESA-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 XMA "SYSTEMATIC NAME" ACDLabs 10.04 "(8aS)-7-[(6-chloronaphthalen-2-yl)sulfonyl]-8a-(methoxymethyl)-1'-pyridin-4-yltetrahydro-5H-spiro[1,3-oxazolo[3,2-a]pyrazine-2,4'-piperidin]-5-one" XMA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(7S,8aS)-7-(6-chloronaphthalen-2-yl)sulfonyl-8a-(methoxymethyl)-1'-pyridin-4-yl-spiro[6,8-dihydro-3H-[1,3]oxazolo[2,3-f]pyrazine-2,4'-piperidine]-5-one" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site XMA "Create component" 2001-03-12 RCSB XMA "Modify descriptor" 2011-06-04 RCSB #