data_2X4
# 
_chem_comp.id                                    2X4 
_chem_comp.name                                  "(4R,4a'S,10a'S)-7'-(5-chloropyridin-3-yl)-3',4',4a',10a'-tetrahydro-1'H-spiro[1,3-oxazole-4,5'-pyrano[3,4-b]chromen]-2-amine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H18 Cl N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2014-04-01 
_chem_comp.pdbx_modified_date                    2014-05-09 
_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                        371.818 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     2X4 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4PZW 
_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 
2X4 C1  C1  C  0 1 N N N 21.037 11.591 7.100  5.797  0.277  -0.591 C1  2X4 1  
2X4 O2  O2  O  0 1 N N N 21.684 10.607 7.906  5.759  1.377  0.320  O2  2X4 2  
2X4 C3  C3  C  0 1 N N N 23.107 10.617 7.914  4.630  2.237  0.152  C3  2X4 3  
2X4 C4  C4  C  0 1 N N S 23.597 11.977 8.457  3.345  1.442  0.389  C4  2X4 4  
2X4 C5  C5  C  0 1 N N S 22.915 13.175 7.743  3.302  0.258  -0.590 C5  2X4 5  
2X4 C6  C6  C  0 1 N N N 21.377 13.007 7.614  4.556  -0.596 -0.388 C6  2X4 6  
2X4 O7  O7  O  0 1 N N N 24.997 12.043 8.233  2.212  2.280  0.155  O7  2X4 7  
2X4 C8  C8  C  0 1 Y N N 25.618 13.216 8.568  0.987  1.695  0.092  C8  2X4 8  
2X4 C9  C9  C  0 1 Y N N 24.896 14.440 8.643  0.845  0.333  -0.130 C9  2X4 9  
2X4 C10 C10 C  0 1 N N R 23.393 14.531 8.317  2.057  -0.564 -0.285 C10 2X4 10 
2X4 C11 C11 C  0 1 Y N N 27.008 13.167 8.853  -0.141 2.494  0.254  C11 2X4 11 
2X4 C12 C12 C  0 1 Y N N 27.696 14.350 9.217  -1.401 1.940  0.193  C12 2X4 12 
2X4 C13 C13 C  0 1 Y N N 26.982 15.576 9.289  -1.548 0.573  -0.032 C13 2X4 13 
2X4 C14 C14 C  0 1 Y N N 25.589 15.617 9.007  -0.418 -0.226 -0.193 C14 2X4 14 
2X4 N15 N15 N  0 1 N N N 22.610 14.845 9.498  2.252  -1.393 0.912  N15 2X4 15 
2X4 C16 C16 C  0 1 N N N 22.051 16.051 9.365  1.847  -2.598 0.641  C16 2X4 16 
2X4 O17 O17 O  0 1 N N N 22.221 16.609 8.139  1.369  -2.743 -0.612 O17 2X4 17 
2X4 C18 C18 C  0 1 N N N 23.100 15.749 7.402  1.821  -1.613 -1.389 C18 2X4 18 
2X4 C19 C19 C  0 1 Y N N 27.624 16.777 9.654  -2.901 -0.030 -0.101 C19 2X4 19 
2X4 C20 C20 C  0 1 Y N N 26.987 17.656 10.569 -4.040 0.763  0.060  C20 2X4 20 
2X4 C21 C21 C  0 1 Y N N 27.639 18.867 10.906 -5.282 0.152  -0.013 C21 2X4 21 
2X4 C22 C22 C  0 1 Y N N 28.907 19.144 10.334 -5.353 -1.211 -0.240 C22 2X4 22 
2X4 N23 N23 N  0 1 Y N N 29.505 18.299 9.465  -4.259 -1.934 -0.387 N23 2X4 23 
2X4 C24 C24 C  0 1 Y N N 28.890 17.144 9.125  -3.058 -1.396 -0.331 C24 2X4 24 
2X4 N25 N25 N  0 1 N N N 21.176 16.612 10.207 1.902  -3.629 1.547  N25 2X4 25 
2X4 CL1 CL1 CL 0 0 N N N 26.907 19.969 11.997 -6.733 1.086  0.179  CL1 2X4 26 
2X4 H1  H1  H  0 1 N N N 19.948 11.439 7.145  5.813  0.653  -1.614 H1  2X4 27 
2X4 H2  H2  H  0 1 N N N 21.378 11.490 6.059  6.693  -0.316 -0.408 H2  2X4 28 
2X4 H3  H3  H  0 1 N N N 23.478 9.807  8.559  4.688  3.057  0.867  H3  2X4 29 
2X4 H4  H4  H  0 1 N N N 23.483 10.472 6.890  4.628  2.638  -0.862 H4  2X4 30 
2X4 H5  H5  H  0 1 N N N 23.374 12.032 9.533  3.324  1.073  1.414  H5  2X4 31 
2X4 H6  H6  H  0 1 N N N 23.295 13.149 6.711  3.256  0.628  -1.613 H6  2X4 32 
2X4 H7  H7  H  0 1 N N N 20.988 13.754 6.906  4.562  -1.412 -1.112 H7  2X4 33 
2X4 H8  H8  H  0 1 N N N 20.911 13.158 8.599  4.560  -1.005 0.623  H8  2X4 34 
2X4 H9  H9  H  0 1 N N N 27.540 12.229 8.792  -0.029 3.553  0.429  H9  2X4 35 
2X4 H10 H10 H  0 1 N N N 28.753 14.320 9.438  -2.273 2.565  0.319  H10 2X4 36 
2X4 H11 H11 H  0 1 N N N 25.056 16.554 9.071  -0.530 -1.286 -0.368 H11 2X4 37 
2X4 H12 H12 H  0 1 N N N 22.616 15.418 6.472  1.050  -1.283 -2.085 H12 2X4 38 
2X4 H13 H13 H  0 1 N N N 24.034 16.277 7.161  2.748  -1.845 -1.914 H13 2X4 39 
2X4 H14 H14 H  0 1 N N N 26.028 17.407 10.998 -3.955 1.825  0.236  H14 2X4 40 
2X4 H15 H15 H  0 1 N N N 29.411 20.061 10.602 -6.318 -1.692 -0.297 H15 2X4 41 
2X4 H16 H16 H  0 1 N N N 29.378 16.478 8.428  -2.185 -2.020 -0.457 H16 2X4 42 
2X4 H17 H17 H  0 1 N N N 20.664 17.425 9.928  2.256  -3.474 2.437  H17 2X4 43 
2X4 H18 H18 H  0 1 N N N 21.034 16.219 11.115 1.588  -4.511 1.297  H18 2X4 44 
# 
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 
2X4 C1  C6  SING N N 1  
2X4 C1  O2  SING N N 2  
2X4 C18 O17 SING N N 3  
2X4 C18 C10 SING N N 4  
2X4 C6  C5  SING N N 5  
2X4 C5  C10 SING N N 6  
2X4 C5  C4  SING N N 7  
2X4 O2  C3  SING N N 8  
2X4 C3  C4  SING N N 9  
2X4 O17 C16 SING N N 10 
2X4 O7  C4  SING N N 11 
2X4 O7  C8  SING N N 12 
2X4 C10 C9  SING N N 13 
2X4 C10 N15 SING N N 14 
2X4 C8  C9  DOUB Y N 15 
2X4 C8  C11 SING Y N 16 
2X4 C9  C14 SING Y N 17 
2X4 C11 C12 DOUB Y N 18 
2X4 C14 C13 DOUB Y N 19 
2X4 C24 N23 DOUB Y N 20 
2X4 C24 C19 SING Y N 21 
2X4 C12 C13 SING Y N 22 
2X4 C13 C19 SING N N 23 
2X4 C16 N15 DOUB N N 24 
2X4 C16 N25 SING N N 25 
2X4 N23 C22 SING Y N 26 
2X4 C19 C20 DOUB Y N 27 
2X4 C22 C21 DOUB Y N 28 
2X4 C20 C21 SING Y N 29 
2X4 C21 CL1 SING N N 30 
2X4 C1  H1  SING N N 31 
2X4 C1  H2  SING N N 32 
2X4 C3  H3  SING N N 33 
2X4 C3  H4  SING N N 34 
2X4 C4  H5  SING N N 35 
2X4 C5  H6  SING N N 36 
2X4 C6  H7  SING N N 37 
2X4 C6  H8  SING N N 38 
2X4 C11 H9  SING N N 39 
2X4 C12 H10 SING N N 40 
2X4 C14 H11 SING N N 41 
2X4 C18 H12 SING N N 42 
2X4 C18 H13 SING N N 43 
2X4 C20 H14 SING N N 44 
2X4 C22 H15 SING N N 45 
2X4 C24 H16 SING N N 46 
2X4 N25 H17 SING N N 47 
2X4 N25 H18 SING N N 48 
# 
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 
2X4 SMILES           ACDLabs              12.01 "Clc1cc(cnc1)c5cc3c(OC4COCCC4C32N=C(OC2)N)cc5"                                                                                                                        
2X4 InChI            InChI                1.03  "InChI=1S/C19H18ClN3O3/c20-13-5-12(7-22-8-13)11-1-2-16-15(6-11)19(10-25-18(21)23-19)14-3-4-24-9-17(14)26-16/h1-2,5-8,14,17H,3-4,9-10H2,(H2,21,23)/t14-,17-,19-/m1/s1" 
2X4 InChIKey         InChI                1.03  BGRWOLNAPSRJIS-LSBZLQRGSA-N                                                                                                                                           
2X4 SMILES_CANONICAL CACTVS               3.385 "NC1=N[C@]2(CO1)[C@@H]3CCOC[C@H]3Oc4ccc(cc24)c5cncc(Cl)c5"                                                                                                            
2X4 SMILES           CACTVS               3.385 "NC1=N[C]2(CO1)[CH]3CCOC[CH]3Oc4ccc(cc24)c5cncc(Cl)c5"                                                                                                                
2X4 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc2c(cc1c3cc(cnc3)Cl)[C@@]4(COC(=N4)N)[C@@H]5CCOC[C@H]5O2"                                                                                                         
2X4 SMILES           "OpenEye OEToolkits" 1.7.6 "c1cc2c(cc1c3cc(cnc3)Cl)C4(COC(=N4)N)C5CCOCC5O2"                                                                                                                      
# 
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 
2X4 "SYSTEMATIC NAME" ACDLabs              12.01 "(4R,4a'S,10a'S)-7'-(5-chloropyridin-3-yl)-3',4',4a',10a'-tetrahydro-1'H-spiro[1,3-oxazole-4,5'-pyrano[3,4-b]chromen]-2-amine" 
2X4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(4aS,5R,10aS)-7-(5-chloranylpyridin-3-yl)spiro[3,4,4a,10a-tetrahydro-1H-pyrano[3,4-b]chromene-5,4'-5H-1,3-oxazole]-2'-amine"  
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
2X4 "Create component" 2014-04-01 RCSB 
2X4 "Initial release"  2014-05-14 RCSB 
# 
