data_B2U # _chem_comp.id B2U _chem_comp.name "N-[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-D-phenylalanine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H18 Cl N O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2019-01-09 _chem_comp.pdbx_modified_date 2019-02-22 _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 403.813 _chem_comp.one_letter_code ? _chem_comp.three_letter_code B2U _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 6J2W _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 B2U CD1 C1 C 0 1 Y N N -6.591 -3.511 13.794 -3.372 -2.180 -0.062 CD1 B2U 1 B2U CE1 C2 C 0 1 Y N N -7.702 -4.172 14.303 -3.257 -3.244 0.813 CE1 B2U 2 B2U CZ C3 C 0 1 Y N N -8.964 -3.600 14.191 -3.998 -3.262 1.980 CZ B2U 3 B2U CE2 C4 C 0 1 Y N N -9.115 -2.367 13.568 -4.854 -2.216 2.272 CE2 B2U 4 B2U CD2 C5 C 0 1 Y N N -8.003 -1.704 13.059 -4.968 -1.152 1.398 CD2 B2U 5 B2U CG C6 C 0 1 Y N N -6.742 -2.276 13.173 -4.223 -1.131 0.234 CG B2U 6 B2U CB C7 C 0 1 N N N -5.629 -1.610 12.671 -4.347 0.030 -0.720 CB B2U 7 B2U CA C8 C 0 1 N N R -5.432 -1.984 11.200 -3.326 1.107 -0.349 CA B2U 8 B2U C C9 C 0 1 N N N -4.632 -3.287 11.110 -3.532 2.317 -1.223 C B2U 9 B2U O O1 O 0 1 N N N -3.560 -3.338 11.751 -4.708 2.965 -1.206 O B2U 10 B2U OXT O2 O 0 1 N N N -5.103 -4.194 10.391 -2.639 2.704 -1.939 OXT B2U 11 B2U N N1 N 0 1 N N N -4.700 -0.911 10.513 -1.972 0.585 -0.548 N B2U 12 B2U CAN C10 C 0 1 N N N -4.192 -1.088 9.286 -0.941 1.103 0.148 CAN B2U 13 B2U OAX O3 O 0 1 N N N -4.613 -1.915 8.480 -1.135 2.004 0.942 OAX B2U 14 B2U CAA C11 C 0 1 Y N N -3.131 -0.249 8.962 0.423 0.578 -0.053 CAA B2U 15 B2U CAB C12 C 0 1 Y N N -1.971 -0.264 9.727 0.650 -0.456 -0.963 CAB B2U 16 B2U CAC C13 C 0 1 Y N N -0.863 0.471 9.323 1.926 -0.950 -1.156 CAC B2U 17 B2U CLA CL1 CL 0 0 N N N 0.598 0.393 10.236 2.188 -2.235 -2.294 CLAM B2U 18 B2U CAD C14 C 0 1 Y N N -0.929 1.266 8.185 2.995 -0.429 -0.451 CAD B2U 19 B2U CAG C15 C 0 1 N N N 0.144 2.091 7.868 4.380 -0.977 -0.681 CAG B2U 20 B2U CAH C16 C 0 1 N N R -0.250 3.054 6.760 5.280 -0.661 0.513 CAH B2U 21 B2U CAL C17 C 0 1 N N N 1.002 3.745 6.214 6.731 -0.997 0.162 CAL B2U 22 B2U OAI O4 O 0 1 N N N -0.892 2.323 5.707 5.173 0.756 0.835 OAI B2U 23 B2U CAJ C18 C 0 1 N N N -2.097 1.877 6.151 3.932 1.153 1.219 CAJ B2U 24 B2U OAK O5 O 0 1 N N N -3.148 2.001 5.523 3.772 1.926 2.143 OAK B2U 25 B2U CAE C19 C 0 1 Y N N -2.078 1.252 7.392 2.785 0.604 0.465 CAE B2U 26 B2U CAF C20 C 0 1 Y N N -3.175 0.500 7.795 1.500 1.118 0.665 CAF B2U 27 B2U OBB O6 O 0 1 N N N -3.882 -0.072 6.784 1.296 2.125 1.547 OBB B2U 28 B2U HD1 H1 H 0 1 N N N -5.611 -3.956 13.881 -2.793 -2.165 -0.973 HD1 B2U 29 B2U HE1 H2 H 0 1 N N N -7.585 -5.131 14.786 -2.589 -4.061 0.585 HE1 B2U 30 B2U HZ H3 H 0 1 N N N -9.827 -4.114 14.588 -3.909 -4.094 2.663 HZ B2U 31 B2U HE2 H4 H 0 1 N N N -10.096 -1.923 13.479 -5.433 -2.231 3.184 HE2 B2U 32 B2U HD2 H5 H 0 1 N N N -8.120 -0.745 12.576 -5.633 -0.333 1.628 HD2 B2U 33 B2U HB1 H6 H 0 1 N N N -4.737 -1.901 13.246 -4.160 -0.314 -1.737 HB1 B2U 34 B2U HB2 H7 H 0 1 N N N -5.782 -0.524 12.756 -5.353 0.445 -0.657 HB2 B2U 35 B2U HAM H8 H 0 1 N N N -6.415 -2.130 10.729 -3.457 1.387 0.696 HAM B2U 36 B2U H1 H9 H 0 1 N N N -3.146 -4.182 11.611 -4.793 3.735 -1.784 H1 B2U 37 B2U H H10 H 0 1 N N N -4.578 -0.030 10.971 -1.817 -0.133 -1.181 H B2U 38 B2U HAB H11 H 0 1 N N N -1.931 -0.847 10.635 -0.177 -0.873 -1.519 HAB B2U 39 B2U HAH H12 H 0 1 N N N 0.990 1.474 7.531 4.322 -2.058 -0.813 HAH B2U 40 B2U HAG H13 H 0 1 N N N 0.439 2.663 8.760 4.803 -0.526 -1.578 HAG B2U 41 B2U HAI H14 H 0 1 N N N -0.931 3.815 7.168 4.967 -1.254 1.373 HAI B2U 42 B2U HA2 H15 H 0 1 N N N 1.494 4.306 7.022 7.044 -0.403 -0.696 HA2 B2U 43 B2U HA3 H16 H 0 1 N N N 1.695 2.988 5.818 7.373 -0.772 1.014 HA3 B2U 44 B2U HA1 H17 H 0 1 N N N 0.717 4.438 5.409 6.810 -2.057 -0.081 HA1 B2U 45 B2U H2 H18 H 0 1 N N N -3.844 0.485 6.016 1.373 3.008 1.161 H2 B2U 46 # # 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 B2U OAK CAJ DOUB N N 1 B2U OAI CAJ SING N N 2 B2U OAI CAH SING N N 3 B2U CAJ CAE SING N N 4 B2U CAL CAH SING N N 5 B2U CAH CAG SING N N 6 B2U OBB CAF SING N N 7 B2U CAE CAF DOUB Y N 8 B2U CAE CAD SING Y N 9 B2U CAF CAA SING Y N 10 B2U CAG CAD SING N N 11 B2U CAD CAC DOUB Y N 12 B2U OAX CAN DOUB N N 13 B2U CAA CAN SING N N 14 B2U CAA CAB DOUB Y N 15 B2U CAN N SING N N 16 B2U CAC CAB SING Y N 17 B2U CAC CLA SING N N 18 B2U OXT C DOUB N N 19 B2U N CA SING N N 20 B2U C CA SING N N 21 B2U C O SING N N 22 B2U CA CB SING N N 23 B2U CB CG SING N N 24 B2U CD2 CG DOUB Y N 25 B2U CD2 CE2 SING Y N 26 B2U CG CD1 SING Y N 27 B2U CE2 CZ DOUB Y N 28 B2U CD1 CE1 DOUB Y N 29 B2U CZ CE1 SING Y N 30 B2U CD1 HD1 SING N N 31 B2U CE1 HE1 SING N N 32 B2U CZ HZ SING N N 33 B2U CE2 HE2 SING N N 34 B2U CD2 HD2 SING N N 35 B2U CB HB1 SING N N 36 B2U CB HB2 SING N N 37 B2U CA HAM SING N N 38 B2U O H1 SING N N 39 B2U N H SING N N 40 B2U CAB HAB SING N N 41 B2U CAG HAH SING N N 42 B2U CAG HAG SING N N 43 B2U CAH HAI SING N N 44 B2U CAL HA2 SING N N 45 B2U CAL HA3 SING N N 46 B2U CAL HA1 SING N N 47 B2U OBB H2 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 B2U SMILES ACDLabs 12.01 "c1ccccc1CC(C(O)=O)NC(=O)c3cc(Cl)c2CC(C)OC(c2c3O)=O" B2U InChI InChI 1.03 "InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15-/m1/s1" B2U InChIKey InChI 1.03 RWQKHEORZBHNRI-MEBBXXQBSA-N B2U SMILES_CANONICAL CACTVS 3.385 "C[C@@H]1Cc2c(Cl)cc(c(O)c2C(=O)O1)C(=O)N[C@H](Cc3ccccc3)C(O)=O" B2U SMILES CACTVS 3.385 "C[CH]1Cc2c(Cl)cc(c(O)c2C(=O)O1)C(=O)N[CH](Cc3ccccc3)C(O)=O" B2U SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C[C@@H]1Cc2c(cc(c(c2C(=O)O1)O)C(=O)N[C@H](Cc3ccccc3)C(=O)O)Cl" B2U SMILES "OpenEye OEToolkits" 2.0.6 "CC1Cc2c(cc(c(c2C(=O)O1)O)C(=O)NC(Cc3ccccc3)C(=O)O)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 B2U "SYSTEMATIC NAME" ACDLabs 12.01 "N-[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-D-phenylalanine" B2U "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{R})-2-[[(3~{R})-5-chloranyl-3-methyl-8-oxidanyl-1-oxidanylidene-3,4-dihydroisochromen-7-yl]carbonylamino]-3-phenyl-propanoic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site B2U "Create component" 2019-01-09 PDBJ B2U "Initial release" 2019-02-27 RCSB ##