data_JAD # _chem_comp.id JAD _chem_comp.name "2-chloro-4-[(3S,3aS,4S)-4-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl]-3-methylbenzonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C15 H16 Cl N3 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-07-04 _chem_comp.pdbx_modified_date 2015-06-12 _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 305.759 _chem_comp.one_letter_code ? _chem_comp.three_letter_code JAD _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 4QL8 _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 JAD CL1 CL1 CL 0 0 N N N 23.641 5.021 4.081 -3.707 -1.703 0.934 CL1 JAD 1 JAD C3 C3 C 0 1 Y N N 25.371 4.557 3.988 -2.769 -0.356 0.369 C3 JAD 2 JAD C2 C2 C 0 1 Y N N 26.314 5.559 3.810 -3.409 0.767 -0.171 C2 JAD 3 JAD C7 C7 C 0 1 N N N 25.962 6.793 3.713 -4.838 0.804 -0.258 C7 JAD 4 JAD N1 N1 N 0 1 N N N 25.664 7.912 3.662 -5.971 0.834 -0.327 N1 JAD 5 JAD C4 C4 C 0 1 Y N N 25.749 3.216 4.098 -1.396 -0.386 0.456 C4 JAD 6 JAD C8 C8 C 0 1 N N N 24.655 2.188 4.291 -0.702 -1.590 1.042 C8 JAD 7 JAD C5 C5 C 0 1 Y N N 27.108 2.879 4.019 -0.645 0.702 0.000 C5 JAD 8 JAD C6 C6 C 0 1 Y N N 28.045 3.902 3.843 -1.289 1.819 -0.543 C6 JAD 9 JAD C1 C1 C 0 1 Y N N 27.659 5.230 3.737 -2.652 1.851 -0.625 C1 JAD 10 JAD C9 C9 C 0 1 N N N 27.649 1.472 4.124 0.825 0.673 0.092 C9 JAD 11 JAD C11 C11 C 0 1 N N S 29.069 1.190 4.471 1.732 -0.271 -0.671 C11 JAD 12 JAD O2 O2 O 0 1 N N N 29.319 1.676 5.785 1.457 -0.210 -2.072 O2 JAD 13 JAD C15 C15 C 0 1 N N N 30.699 1.822 6.104 0.551 -1.215 -2.531 C15 JAD 14 JAD C10 C10 C 0 1 N N S 29.107 -0.321 4.408 3.137 0.266 -0.372 C10 JAD 15 JAD C14 C14 C 0 1 N N S 29.797 -0.883 3.169 4.068 -0.821 0.188 C14 JAD 16 JAD O1 O1 O 0 1 N N N 30.987 -1.598 3.509 4.980 -1.264 -0.819 O1 JAD 17 JAD C13 C13 C 0 1 N N N 28.799 -1.812 2.503 4.830 -0.118 1.337 C13 JAD 18 JAD C12 C12 C 0 1 N N N 27.546 -1.803 3.371 4.242 1.315 1.383 C12 JAD 19 JAD N3 N3 N 0 1 N N N 27.689 -0.707 4.343 2.900 1.177 0.779 N3 JAD 20 JAD N2 N2 N 0 1 N N N 27.021 0.389 3.959 1.543 1.453 0.833 N2 JAD 21 JAD H1 H1 H 0 1 N N N 24.307 1.834 3.310 -0.461 -2.293 0.245 H1 JAD 22 JAD H2 H2 H 0 1 N N N 25.048 1.339 4.869 0.215 -1.275 1.539 H2 JAD 23 JAD H3 H3 H 0 1 N N N 23.815 2.644 4.835 -1.360 -2.072 1.765 H3 JAD 24 JAD H4 H4 H 0 1 N N N 29.094 3.652 3.788 -0.708 2.658 -0.894 H4 JAD 25 JAD H5 H5 H 0 1 N N N 28.401 6.002 3.599 -3.146 2.717 -1.041 H5 JAD 26 JAD H7 H7 H 0 1 N N N 29.753 1.629 3.730 1.621 -1.291 -0.303 H7 JAD 27 JAD H8 H8 H 0 1 N N N 30.800 2.200 7.132 0.402 -1.107 -3.605 H8 JAD 28 JAD H9 H9 H 0 1 N N N 31.200 0.846 6.022 0.964 -2.201 -2.318 H9 JAD 29 JAD H10 H10 H 0 1 N N N 31.164 2.533 5.405 -0.405 -1.103 -2.019 H10 JAD 30 JAD H11 H11 H 0 1 N N N 29.579 -0.725 5.316 3.573 0.780 -1.229 H11 JAD 31 JAD H12 H12 H 0 1 N N N 30.031 -0.055 2.483 3.487 -1.660 0.571 H12 JAD 32 JAD H13 H13 H 0 1 N N N 31.604 -1.007 3.925 5.592 -1.951 -0.520 H13 JAD 33 JAD H14 H14 H 0 1 N N N 28.562 -1.451 1.491 4.652 -0.632 2.281 H14 JAD 34 JAD H15 H15 H 0 1 N N N 29.211 -2.830 2.442 5.898 -0.083 1.118 H15 JAD 35 JAD H16 H16 H 0 1 N N N 26.657 -1.636 2.745 4.167 1.664 2.413 H16 JAD 36 JAD H17 H17 H 0 1 N N N 27.448 -2.763 3.899 4.851 1.997 0.791 H17 JAD 37 # 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 JAD C13 C14 SING N N 1 JAD C13 C12 SING N N 2 JAD C14 O1 SING N N 3 JAD C14 C10 SING N N 4 JAD C12 N3 SING N N 5 JAD N1 C7 TRIP N N 6 JAD C7 C2 SING N N 7 JAD C1 C2 DOUB Y N 8 JAD C1 C6 SING Y N 9 JAD C2 C3 SING Y N 10 JAD C6 C5 DOUB Y N 11 JAD N2 C9 DOUB N N 12 JAD N2 N3 SING N N 13 JAD C3 CL1 SING N N 14 JAD C3 C4 DOUB Y N 15 JAD C5 C4 SING Y N 16 JAD C5 C9 SING N N 17 JAD C4 C8 SING N N 18 JAD C9 C11 SING N N 19 JAD N3 C10 SING N N 20 JAD C10 C11 SING N N 21 JAD C11 O2 SING N N 22 JAD O2 C15 SING N N 23 JAD C8 H1 SING N N 24 JAD C8 H2 SING N N 25 JAD C8 H3 SING N N 26 JAD C6 H4 SING N N 27 JAD C1 H5 SING N N 28 JAD C11 H7 SING N N 29 JAD C15 H8 SING N N 30 JAD C15 H9 SING N N 31 JAD C15 H10 SING N N 32 JAD C10 H11 SING N N 33 JAD C14 H12 SING N N 34 JAD O1 H13 SING N N 35 JAD C13 H14 SING N N 36 JAD C13 H15 SING N N 37 JAD C12 H16 SING N N 38 JAD C12 H17 SING N N 39 # 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 JAD SMILES ACDLabs 12.01 "N#Cc3ccc(C2=NN1CCC(O)C1C2OC)c(c3Cl)C" JAD InChI InChI 1.03 "InChI=1S/C15H16ClN3O2/c1-8-10(4-3-9(7-17)12(8)16)13-15(21-2)14-11(20)5-6-19(14)18-13/h3-4,11,14-15,20H,5-6H2,1-2H3/t11-,14-,15+/m0/s1" JAD InChIKey InChI 1.03 RJZJEPYCJHLWQR-TUKIKUTGSA-N JAD SMILES_CANONICAL CACTVS 3.385 "CO[C@H]1[C@@H]2[C@@H](O)CCN2N=C1c3ccc(C#N)c(Cl)c3C" JAD SMILES CACTVS 3.385 "CO[CH]1[CH]2[CH](O)CCN2N=C1c3ccc(C#N)c(Cl)c3C" JAD SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1c(ccc(c1Cl)C#N)C2=NN3CC[C@@H]([C@H]3[C@@H]2OC)O" JAD SMILES "OpenEye OEToolkits" 1.7.6 "Cc1c(ccc(c1Cl)C#N)C2=NN3CCC(C3C2OC)O" # 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 JAD "SYSTEMATIC NAME" ACDLabs 12.01 "2-chloro-4-[(3S,3aS,4S)-4-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl]-3-methylbenzonitrile" JAD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "4-[(3S,3aS,4S)-3-methoxy-4-oxidanyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl]-2-chloranyl-3-methyl-benzenecarbonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site JAD "Create component" 2014-07-04 PDBJ JAD "Modify name" 2014-07-07 PDBJ JAD "Initial release" 2015-06-17 RCSB #