data_C2D # _chem_comp.id C2D _chem_comp.name "6-CHLORO-1-(2-{[(5-CHLORO-1-BENZOTHIEN-3-YL)METHYL]AMINO}ETHYL)-3-[(2-PYRIDIN-2-YLETHYL)AMINO]-1,4-DIHYDROPYRAZIN-2-OL" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H31 Cl2 N5 O S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-07-27 _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 484.485 _chem_comp.one_letter_code ? _chem_comp.three_letter_code C2D _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2BXT _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 C2D O1 O1 O 0 1 N N N 12.172 -13.121 13.027 2.336 1.312 -3.641 O1 C2D 1 C2D CL2 CL2 CL 0 0 N N N 16.423 -8.334 11.004 2.457 6.927 1.555 CL2 C2D 2 C2D CL3 CL3 CL 0 0 N N N 8.138 -12.637 15.979 4.811 1.160 -7.701 CL3 C2D 3 C2D C4 C4 C 0 1 Y N N 17.740 -10.733 11.480 4.295 8.741 0.779 C4 C2D 4 C2D C5 C5 C 0 1 Y N N 17.906 -11.974 12.189 5.417 9.169 0.067 C5 C2D 5 C2D C6 C6 C 0 1 Y N N 16.674 -9.836 11.828 3.841 7.435 0.666 C6 C2D 6 C2D C7 C7 C 0 1 Y N N 16.991 -12.303 13.235 6.083 8.252 -0.770 C7 C2D 7 C2D C8 C8 C 0 1 Y N N 15.781 -10.180 12.868 4.504 6.527 -0.164 C8 C2D 8 C2D C9 C9 C 0 1 Y N N 15.953 -11.411 13.556 5.645 6.930 -0.900 C9 C2D 9 C2D S10 S10 S 0 1 Y N N 16.895 -13.627 14.204 7.478 8.549 -1.738 S10 C2D 10 C2D C11 C11 C 0 1 Y N N 15.610 -13.112 15.026 7.504 6.949 -2.324 C11 C2D 11 C2D C12 C12 C 0 1 Y N N 15.154 -11.870 14.581 6.483 6.209 -1.800 C12 C2D 12 C2D C13 C13 C 0 1 N N N 13.972 -11.057 15.070 6.273 4.764 -2.150 C13 C2D 13 C2D N14 N14 N 0 1 N N N 13.267 -11.618 16.240 5.399 4.604 -3.313 N14 C2D 14 C2D C15 C15 C 0 1 N N N 11.917 -12.265 16.135 5.231 3.220 -3.663 C15 C2D 15 C2D C16 C16 C 0 1 N N N 10.932 -11.761 15.044 4.343 3.045 -4.884 C16 C2D 16 C2D C17 C17 C 0 1 N N S 9.020 -13.419 14.713 3.491 1.459 -6.519 C17 C2D 17 C2D N18 N18 N 0 1 N N N 10.315 -12.920 14.347 4.153 1.641 -5.230 N18 C2D 18 C2D C19 C19 C 0 1 N N N 8.490 -14.480 14.063 2.501 0.293 -6.567 C19 C2D 19 C2D C20 C20 C 0 1 N N R 11.060 -13.540 13.328 3.587 0.861 -4.133 C20 C2D 20 C2D N21 N21 N 0 1 N N N 9.266 -15.155 12.964 2.952 -0.858 -5.781 N21 C2D 21 C2D C22 C22 C 0 1 N N N 10.470 -14.721 12.617 3.451 -0.580 -4.616 C22 C2D 22 C2D N23 N23 N 0 1 N N N 11.194 -15.327 11.605 3.878 -1.556 -3.750 N23 C2D 23 C2D C24 C24 C 0 1 N N N 10.861 -16.497 10.746 3.791 -2.938 -4.117 C24 C2D 24 C2D C25 C25 C 0 1 N N N 10.125 -16.074 9.449 4.295 -3.864 -3.016 C25 C2D 25 C2D C26 C26 C 0 1 N N N 7.709 -16.151 10.264 4.053 -4.672 -0.644 C26 C2D 26 C2D C27 C27 C 0 1 N N R 8.797 -15.426 9.758 3.494 -3.733 -1.722 C27 C2D 27 C2D C28 C28 C 0 1 N N N 6.504 -15.472 10.552 3.216 -4.613 0.630 C28 C2D 28 C2D N29 N29 N 0 1 N N N 8.657 -14.042 9.563 2.084 -4.038 -1.996 N29 C2D 29 C2D C30 C30 C 0 1 N N N 6.375 -14.091 10.341 1.743 -4.846 0.314 C30 C2D 30 C2D C31 C31 C 0 1 N N N 7.462 -13.367 9.837 1.260 -3.913 -0.794 C31 C2D 31 C2D H1 H1 H 0 1 N N N 12.226 -13.013 12.085 2.172 0.834 -2.812 H1 C2D 32 C2D H4 H4 H 0 1 N N N 18.421 -10.475 10.682 3.783 9.452 1.423 H4 C2D 33 C2D H5 H5 H 0 1 N N N 18.711 -12.647 11.934 5.765 10.193 0.161 H5 C2D 34 C2D H8 H8 H 0 1 N N N 14.975 -9.513 13.137 4.146 5.503 -0.249 H8 C2D 35 C2D H11 H11 H 0 1 N N N 15.152 -13.666 15.832 8.268 6.638 -3.024 H11 C2D 36 C2D H131 1H13 H 0 0 N N N 13.243 -11.044 14.246 7.228 4.279 -2.377 H131 C2D 37 C2D H132 2H13 H 0 0 N N N 14.346 -10.062 15.352 5.822 4.219 -1.315 H132 C2D 38 C2D H14 H14 H 0 1 N N N 13.873 -12.328 16.599 4.490 5.027 -3.094 H14 C2D 39 C2D H151 1H15 H 0 0 N N N 11.421 -12.019 17.086 4.785 2.721 -2.797 H151 C2D 40 C2D H152 2H15 H 0 0 N N N 12.096 -13.330 15.927 6.227 2.799 -3.831 H152 C2D 41 C2D H161 1H16 H 0 0 N N N 11.482 -11.149 14.314 4.768 3.544 -5.761 H161 C2D 42 C2D H162 2H16 H 0 0 N N N 10.143 -11.157 15.516 3.351 3.465 -4.691 H162 C2D 43 C2D H117 17H1 H 0 0 N N N 8.984 -14.501 14.978 2.977 2.367 -6.854 H117 C2D 44 C2D H19 H19 H 0 1 N N N 8.206 -15.250 14.818 1.526 0.615 -6.177 H19 C2D 45 C2D H191 1H19 H 0 0 N N N 7.493 -14.184 13.660 2.323 -0.030 -7.599 H191 C2D 46 C2D H220 20H2 H 0 0 N N N 12.084 -13.225 13.019 4.288 0.875 -3.290 H220 C2D 47 C2D H23 H23 H 0 1 N N N 11.315 -14.588 10.942 4.240 -1.247 -2.883 H23 C2D 48 C2D H241 1H24 H 0 0 N N N 10.194 -17.160 11.316 4.395 -3.068 -5.020 H241 C2D 49 C2D H242 2H24 H 0 0 N N N 11.795 -17.007 10.470 2.748 -3.153 -4.370 H242 C2D 50 C2D H251 1H25 H 0 0 N N N 9.941 -16.974 8.844 4.227 -4.900 -3.366 H251 C2D 51 C2D H252 2H25 H 0 0 N N N 10.753 -15.355 8.902 5.352 -3.660 -2.807 H252 C2D 52 C2D H26 H26 H 0 1 N N N 8.038 -16.700 11.177 5.090 -4.400 -0.413 H26 C2D 53 C2D H261 1H26 H 0 0 N N N 7.487 -16.995 9.570 4.072 -5.704 -1.018 H261 C2D 54 C2D H227 27H2 H 0 0 N N N 8.694 -16.439 9.304 3.578 -2.693 -1.384 H227 C2D 55 C2D H28 H28 H 0 1 N N N 6.235 -15.684 11.613 3.338 -3.631 1.104 H28 C2D 56 C2D H281 1H28 H 0 0 N N N 5.681 -15.982 9.999 3.569 -5.363 1.346 H281 C2D 57 C2D H30 H30 H 0 1 N N N 5.493 -13.912 9.683 1.596 -5.890 0.007 H30 C2D 58 C2D H301 1H30 H 0 0 N N N 6.041 -13.615 11.292 1.142 -4.691 1.217 H301 C2D 59 C2D H31 H31 H 0 1 N N N 7.679 -12.518 10.526 0.222 -4.155 -1.049 H31 C2D 60 C2D H311 1H31 H 0 0 N N N 7.137 -12.824 8.919 1.263 -2.873 -0.446 H311 C2D 61 C2D HN1 HN1 H 0 1 N N N 9.343 -13.619 10.155 2.011 -4.992 -2.353 HN1 C2D 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 C2D O1 C20 SING N N 1 C2D O1 H1 SING N N 2 C2D CL2 C6 SING N N 3 C2D CL3 C17 SING N N 4 C2D C4 C5 SING Y N 5 C2D C4 C6 DOUB Y N 6 C2D C4 H4 SING N N 7 C2D C5 C7 DOUB Y N 8 C2D C5 H5 SING N N 9 C2D C6 C8 SING Y N 10 C2D C7 C9 SING Y N 11 C2D C7 S10 SING Y N 12 C2D C8 C9 DOUB Y N 13 C2D C8 H8 SING N N 14 C2D C9 C12 SING Y N 15 C2D S10 C11 SING Y N 16 C2D C11 C12 DOUB Y N 17 C2D C11 H11 SING N N 18 C2D C12 C13 SING N N 19 C2D C13 N14 SING N N 20 C2D C13 H131 SING N N 21 C2D C13 H132 SING N N 22 C2D N14 C15 SING N N 23 C2D N14 H14 SING N N 24 C2D C15 C16 SING N N 25 C2D C15 H151 SING N N 26 C2D C15 H152 SING N N 27 C2D C16 N18 SING N N 28 C2D C16 H161 SING N N 29 C2D C16 H162 SING N N 30 C2D C17 N18 SING N N 31 C2D C17 C19 SING N N 32 C2D C17 H117 SING N N 33 C2D N18 C20 SING N N 34 C2D C19 N21 SING N N 35 C2D C19 H19 SING N N 36 C2D C19 H191 SING N N 37 C2D C20 C22 SING N N 38 C2D C20 H220 SING N N 39 C2D N21 C22 DOUB N N 40 C2D C22 N23 SING N N 41 C2D N23 C24 SING N N 42 C2D N23 H23 SING N N 43 C2D C24 C25 SING N N 44 C2D C24 H241 SING N N 45 C2D C24 H242 SING N N 46 C2D C25 C27 SING N N 47 C2D C25 H251 SING N N 48 C2D C25 H252 SING N N 49 C2D C26 C27 SING N N 50 C2D C26 C28 SING N N 51 C2D C26 H26 SING N N 52 C2D C26 H261 SING N N 53 C2D C27 N29 SING N N 54 C2D C27 H227 SING N N 55 C2D C28 C30 SING N N 56 C2D C28 H28 SING N N 57 C2D C28 H281 SING N N 58 C2D N29 C31 SING N N 59 C2D C30 C31 SING N N 60 C2D C30 H30 SING N N 61 C2D C30 H301 SING N N 62 C2D C31 H31 SING N N 63 C2D C31 H311 SING N N 64 C2D HN1 N29 SING N N 65 # 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 C2D SMILES ACDLabs 10.04 "ClC1N(C(O)C(=NC1)NCCC2NCCCC2)CCNCc3c4cc(Cl)ccc4sc3" C2D SMILES_CANONICAL CACTVS 3.341 "O[C@H]1N(CCNCc2csc3ccc(Cl)cc23)[C@@H](Cl)CN=C1NCC[C@H]4CCCCN4" C2D SMILES CACTVS 3.341 "O[CH]1N(CCNCc2csc3ccc(Cl)cc23)[CH](Cl)CN=C1NCC[CH]4CCCCN4" C2D SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc2c(cc1Cl)c(cs2)CNCCN3C(CN=C(C3O)NCCC4CCCCN4)Cl" C2D SMILES "OpenEye OEToolkits" 1.5.0 "c1cc2c(cc1Cl)c(cs2)CNCCN3C(CN=C(C3O)NCCC4CCCCN4)Cl" C2D InChI InChI 1.03 "InChI=1S/C22H31Cl2N5OS/c23-16-4-5-19-18(11-16)15(14-31-19)12-25-9-10-29-20(24)13-28-21(22(29)30)27-8-6-17-3-1-2-7-26-17/h4-5,11,14,17,20,22,25-26,30H,1-3,6-10,12-13H2,(H,27,28)/t17-,20-,22?/m1/s1" C2D InChIKey InChI 1.03 YHTGPUXGIBWHPN-IKQMYLSPSA-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 C2D "SYSTEMATIC NAME" ACDLabs 10.04 "(2R,6S)-6-chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2R)-piperidin-2-yl]ethyl}amino)-1,2,5,6-tetrahydropyrazin-2-ol" C2D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "6-chloro-1-[2-[(5-chloro-1-benzothiophen-3-yl)methylamino]ethyl]-3-(2-piperidin-2-ylethylamino)-5,6-dihydro-2H-pyrazin-2-ol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site C2D "Create component" 2005-07-27 EBI C2D "Modify descriptor" 2011-06-04 RCSB #