data_XC2
# 
_chem_comp.id                                    XC2 
_chem_comp.name                                  "(3R)-8-CYCLOPROPYL-6-(MORPHOLIN-4-YLMETHYL)-7-(1-NAPHTHYLMETHYL)-5-OXO-2,3-DIHYDRO-5H-[1,3]THIAZOLO[3,2-A]PYRIDINE-3-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H28 N2 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-12 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        476.587 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XC2 
_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        2J7L 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
XC2 S6   S6   S 0 1 N N N 32.358 28.889 38.183 -2.579 -6.897 -0.963 S6   XC2 1  
XC2 C5   C5   C 0 1 N N N 30.886 28.254 39.005 -1.119 -7.863 -1.453 C5   XC2 2  
XC2 C11  C11  C 0 1 N N S 29.736 28.599 38.041 -0.228 -6.863 -2.173 C11  XC2 3  
XC2 N10  N10  N 0 1 Y N N 30.287 28.415 36.684 -0.495 -5.525 -1.641 N10  XC2 4  
XC2 C6   C6   C 0 1 Y N N 31.606 28.535 36.584 -1.713 -5.392 -1.007 C6   XC2 5  
XC2 C7   C7   C 0 1 Y N N 32.277 28.419 35.401 -2.132 -4.223 -0.483 C7   XC2 6  
XC2 C8   C8   C 0 1 Y N N 31.448 28.102 34.158 -1.216 -3.060 -0.575 C8   XC2 7  
XC2 C9   C9   C 0 1 Y N N 30.079 27.972 34.288 -0.020 -3.162 -1.201 C9   XC2 8  
XC2 C10  C10  C 0 1 Y N N 29.492 28.144 35.656 0.413  -4.487 -1.774 C10  XC2 9  
XC2 O25  O25  O 0 1 N N N 28.275 28.026 35.773 1.511  -4.601 -2.318 O25  XC2 10 
XC2 C26  C26  C 0 1 N N N 29.171 27.660 33.112 0.962  -2.041 -1.412 C26  XC2 11 
XC2 N5   N5   N 0 1 N N N 29.386 26.274 32.636 1.422  -2.124 -2.796 N5   XC2 12 
XC2 C1   C1   C 0 1 N N N 28.994 26.181 31.208 0.295  -1.987 -3.729 C1   XC2 13 
XC2 C2   C2   C 0 1 N N N 29.206 24.720 30.710 0.800  -2.066 -5.167 C2   XC2 14 
XC2 O3   O3   O 0 1 N N N 28.469 23.792 31.545 1.773  -1.049 -5.408 O3   XC2 15 
XC2 C34  C34  C 0 1 N N N 28.855 23.861 32.932 2.888  -1.194 -4.527 C34  XC2 16 
XC2 C4   C4   C 0 1 N N N 28.593 25.321 33.465 2.433  -1.095 -3.074 C4   XC2 17 
XC2 C24  C24  C 0 1 N N N 32.130 27.956 32.788 -1.667 -1.778 0.090  C24  XC2 18 
XC2 C15  C15  C 0 1 Y N N 32.666 26.515 32.479 -1.540 -1.846 1.581  C15  XC2 19 
XC2 C20  C20  C 0 1 Y N N 32.685 25.495 33.494 -0.527 -2.652 2.100  C20  XC2 20 
XC2 C19  C19  C 0 1 Y N N 33.170 24.197 33.223 -0.358 -2.756 3.478  C19  XC2 21 
XC2 C18  C18  C 0 1 Y N N 33.655 23.876 31.926 -1.201 -2.054 4.340  C18  XC2 22 
XC2 C17  C17  C 0 1 Y N N 33.653 24.856 30.892 -2.225 -1.238 3.834  C17  XC2 23 
XC2 C21  C21  C 0 1 Y N N 34.142 24.525 29.594 -3.083 -0.525 4.688  C21  XC2 24 
XC2 C27  C27  C 0 1 Y N N 34.142 25.499 28.551 -4.095 0.282  4.167  C27  XC2 25 
XC2 C28  C28  C 0 1 Y N N 33.657 26.811 28.797 -4.265 0.386  2.790  C28  XC2 26 
XC2 C29  C29  C 0 1 Y N N 33.166 27.158 30.092 -3.422 -0.316 1.927  C29  XC2 27 
XC2 C16  C16  C 0 1 Y N N 33.159 26.188 31.159 -2.398 -1.132 2.433  C16  XC2 28 
XC2 C22  C22  C 0 1 N N N 33.791 28.544 35.175 -3.444 -4.018 0.195  C22  XC2 29 
XC2 C31  C31  C 0 1 N N N 34.265 30.015 35.303 -4.669 -4.365 -0.564 C31  XC2 30 
XC2 C30  C30  C 0 1 N N N 34.888 28.862 36.165 -4.314 -2.929 -0.311 C30  XC2 31 
XC2 C23  C23  C 0 1 N N N 29.310 30.075 38.248 -0.524 -6.814 -3.646 C23  XC2 32 
XC2 O33  O33  O 0 1 N N N 28.785 30.384 39.434 0.282  -7.667 -4.324 O33  XC2 33 
XC2 O32  O32  O 0 1 N N N 29.441 30.918 37.372 -1.373 -6.108 -4.168 O32  XC2 34 
XC2 H5C1 1H5C H 0 0 N N N 30.742 28.635 40.043 -1.401 -8.721 -2.070 H5C1 XC2 35 
XC2 H5C2 2H5C H 0 0 N N N 30.945 27.175 39.278 -0.632 -8.224 -0.541 H5C2 XC2 36 
XC2 H11  H11  H 0 1 N N N 28.839 27.959 38.210 0.833  -7.111 -2.059 H11  XC2 37 
XC2 H22  H22  H 0 1 N N N 33.755 27.683 34.468 -3.398 -4.214 1.244  H22  XC2 38 
XC2 H241 1H24 H 0 0 N N N 32.948 28.706 32.680 -2.702 -1.590 -0.195 H241 XC2 39 
XC2 H242 2H24 H 0 0 N N N 31.447 28.299 31.976 -1.074 -0.959 -0.316 H242 XC2 40 
XC2 H261 1H26 H 0 0 N N N 29.292 28.403 32.289 1.786  -2.174 -0.716 H261 XC2 41 
XC2 H262 2H26 H 0 0 N N N 28.100 27.851 33.355 0.452  -1.100 -1.224 H262 XC2 42 
XC2 H1C1 1H1C H 0 0 N N N 29.529 26.926 30.573 -0.211 -1.026 -3.570 H1C1 XC2 43 
XC2 H1C2 2H1C H 0 0 N N N 27.954 26.541 31.031 -0.435 -2.787 -3.561 H1C2 XC2 44 
XC2 H4C1 1H4C H 0 0 N N N 27.508 25.578 33.495 3.300  -1.231 -2.417 H4C1 XC2 45 
XC2 H4C2 2H4C H 0 0 N N N 28.803 25.424 34.555 2.017  -0.096 -2.885 H4C2 XC2 46 
XC2 H2C1 1H2C H 0 0 N N N 30.287 24.455 30.647 1.234  -3.048 -5.390 H2C1 XC2 47 
XC2 H2C2 2H2C H 0 0 N N N 28.946 24.606 29.632 -0.029 -1.904 -5.863 H2C2 XC2 48 
XC2 H341 1H34 H 0 0 N N N 28.349 23.085 33.553 3.596  -0.389 -4.751 H341 XC2 49 
XC2 H342 2H34 H 0 0 N N N 29.907 23.531 33.097 3.393  -2.146 -4.729 H342 XC2 50 
XC2 H20  H20  H 0 1 N N N 32.317 25.715 34.510 0.135  -3.204 1.439  H20  XC2 51 
XC2 H19  H19  H 0 1 N N N 33.170 23.436 34.022 0.430  -3.385 3.882  H19  XC2 52 
XC2 H18  H18  H 0 1 N N N 34.035 22.861 31.721 -1.049 -2.151 5.414  H18  XC2 53 
XC2 H21  H21  H 0 1 N N N 34.523 23.509 29.395 -2.969 -0.592 5.767  H21  XC2 54 
XC2 H27  H27  H 0 1 N N N 34.519 25.236 27.548 -4.752 0.828  4.838  H27  XC2 55 
XC2 H28  H28  H 0 1 N N N 33.662 27.558 27.985 -5.054 1.014  2.386  H28  XC2 56 
XC2 H29  H29  H 0 1 N N N 32.791 28.180 30.269 -3.586 -0.208 0.858  H29  XC2 57 
XC2 H311 1H31 H 0 0 N N N 33.784 31.001 35.505 -5.489 -4.787 0.005  H311 XC2 58 
XC2 H312 2H31 H 0 0 N N N 34.649 30.800 34.610 -4.600 -4.727 -1.583 H312 XC2 59 
XC2 H301 1H30 H 0 0 N N N 35.922 28.483 36.339 -4.007 -2.330 -1.161 H301 XC2 60 
XC2 H302 2H30 H 0 0 N N N 35.034 28.689 37.257 -4.896 -2.387 0.425  H302 XC2 61 
XC2 H33  H33  H 0 1 N N N 28.524 31.289 39.561 0.103  -7.651 -5.289 H33  XC2 62 
# 
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 
XC2 S6  C5   SING N N 1  
XC2 S6  C6   SING N N 2  
XC2 C5  C11  SING N N 3  
XC2 C5  H5C1 SING N N 4  
XC2 C5  H5C2 SING N N 5  
XC2 C11 N10  SING N N 6  
XC2 C11 H11  SING N N 7  
XC2 C11 C23  SING N N 8  
XC2 N10 C6   SING Y N 9  
XC2 N10 C10  SING Y N 10 
XC2 C6  C7   DOUB Y N 11 
XC2 C7  C8   SING Y N 12 
XC2 C7  C22  SING N N 13 
XC2 C8  C9   DOUB Y N 14 
XC2 C8  C24  SING N N 15 
XC2 C9  C10  SING Y N 16 
XC2 C9  C26  SING N N 17 
XC2 C10 O25  DOUB N N 18 
XC2 C26 N5   SING N N 19 
XC2 C26 H261 SING N N 20 
XC2 C26 H262 SING N N 21 
XC2 N5  C1   SING N N 22 
XC2 N5  C4   SING N N 23 
XC2 C1  C2   SING N N 24 
XC2 C1  H1C1 SING N N 25 
XC2 C1  H1C2 SING N N 26 
XC2 C2  O3   SING N N 27 
XC2 C2  H2C1 SING N N 28 
XC2 C2  H2C2 SING N N 29 
XC2 O3  C34  SING N N 30 
XC2 C34 C4   SING N N 31 
XC2 C34 H341 SING N N 32 
XC2 C34 H342 SING N N 33 
XC2 C4  H4C1 SING N N 34 
XC2 C4  H4C2 SING N N 35 
XC2 C24 C15  SING N N 36 
XC2 C24 H241 SING N N 37 
XC2 C24 H242 SING N N 38 
XC2 C15 C20  SING Y N 39 
XC2 C15 C16  DOUB Y N 40 
XC2 C20 C19  DOUB Y N 41 
XC2 C20 H20  SING N N 42 
XC2 C19 C18  SING Y N 43 
XC2 C19 H19  SING N N 44 
XC2 C18 C17  DOUB Y N 45 
XC2 C18 H18  SING N N 46 
XC2 C17 C21  SING Y N 47 
XC2 C17 C16  SING Y N 48 
XC2 C21 C27  DOUB Y N 49 
XC2 C21 H21  SING N N 50 
XC2 C27 C28  SING Y N 51 
XC2 C27 H27  SING N N 52 
XC2 C28 C29  DOUB Y N 53 
XC2 C28 H28  SING N N 54 
XC2 C29 C16  SING Y N 55 
XC2 C29 H29  SING N N 56 
XC2 C22 C31  SING N N 57 
XC2 C22 C30  SING N N 58 
XC2 C22 H22  SING N N 59 
XC2 C31 C30  SING N N 60 
XC2 C31 H311 SING N N 61 
XC2 C31 H312 SING N N 62 
XC2 C30 H301 SING N N 63 
XC2 C30 H302 SING N N 64 
XC2 C23 O33  SING N N 65 
XC2 C23 O32  DOUB N N 66 
XC2 O33 H33  SING N N 67 
# 
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 
XC2 SMILES           ACDLabs              10.04 O=C2C(=C(C(=C1SCC(N12)C(=O)O)C3CC3)Cc5c4ccccc4ccc5)CN6CCOCC6                                                                                                                       
XC2 InChI            InChI                1.02b InChI=1/C27H28N2O4S/c30-25-22(15-28-10-12-33-13-11-28)21(14-19-6-3-5-17-4-1-2-7-20(17)19)24(18-8-9-18)26-29(25)23(16-34-26)27(31)32/h1-7,18,23H,8-16H2,(H,31,32)/t23-/m0/s1/f/h31H 
XC2 InChIKey         InChI                1.02b QFNHKTSOHATKEL-QPPRZQIQDX                                                                                                                                                          
XC2 SMILES_CANONICAL CACTVS               3.341 OC(=O)[C@@H]1CSC2=C(C3CC3)C(=C(CN4CCOCC4)C(=O)N12)Cc5cccc6ccccc56                                                                                                                  
XC2 SMILES           CACTVS               3.341 OC(=O)[CH]1CSC2=C(C3CC3)C(=C(CN4CCOCC4)C(=O)N12)Cc5cccc6ccccc56                                                                                                                    
XC2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)cccc2CC3=C(C(=O)N4[C@@H](CSC4=C3C5CC5)C(=O)O)CN6CCOCC6                                                                                                                  
XC2 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)cccc2CC3=C(C(=O)N4C(CSC4=C3C5CC5)C(=O)O)CN6CCOCC6                                                                                                                       
# 
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 
XC2 "SYSTEMATIC NAME" ACDLabs              10.04 "(3R)-8-cyclopropyl-6-(morpholin-4-ylmethyl)-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid" 
XC2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R)-8-cyclopropyl-6-(morpholin-4-ylmethyl)-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid"    
# 
