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                    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                        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 InChI            InChI                1.02b InChI=1/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                1.02b OCCGRNQFQCNISA-MHZLTWQEBA                                                                                                                                                                            
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                                                                                                                                 
# 
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" 
# 
