data_6OS # _chem_comp.id 6OS _chem_comp.name Neplanocin-A _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H13 N5 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-05-16 _chem_comp.pdbx_modified_date 2021-03-13 _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 263.253 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 6OS _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 5JXW _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 6OS C2 C1 C 0 1 Y N N -26.038 -29.425 -1.732 -3.562 -1.079 1.416 C2 6OS 1 6OS C4 C2 C 0 1 Y N N -26.403 -28.641 -3.894 -1.676 -0.298 0.360 C4 6OS 2 6OS C5 C3 C 0 1 Y N N -25.463 -29.631 -4.422 -2.483 0.502 -0.466 C5 6OS 3 6OS C6 C4 C 0 1 Y N N -24.822 -30.521 -3.439 -3.875 0.449 -0.285 C6 6OS 4 6OS "O3'" O1 O 0 1 N N N -29.097 -23.778 -5.857 3.870 -1.002 -1.321 "O3'" 6OS 5 6OS "C3'" C5 C 0 1 N N R -28.677 -25.098 -6.219 2.616 -0.388 -1.017 "C3'" 6OS 6 6OS "C2'" C6 C 0 1 N N S -27.410 -25.611 -5.510 1.597 -1.451 -0.541 "C2'" 6OS 7 6OS "O2'" O2 O 0 1 N N N -26.816 -24.681 -4.607 2.263 -2.583 0.021 "O2'" 6OS 8 6OS "C4'" C7 C 0 1 N N N -29.715 -26.146 -5.948 2.761 0.555 0.155 "C4'" 6OS 9 6OS "C5'" C8 C 0 1 N N N -31.151 -26.099 -6.445 3.888 1.542 0.319 "C5'" 6OS 10 6OS "O5'" O3 O 0 1 N N N -32.066 -26.447 -5.388 3.711 2.269 1.537 "O5'" 6OS 11 6OS "C6'" C9 C 0 1 N N N -29.240 -27.151 -5.227 1.783 0.403 1.005 "C6'" 6OS 12 6OS "C1'" C10 C 0 1 N N R -27.828 -26.873 -4.776 0.822 -0.668 0.543 "C1'" 6OS 13 6OS N9 N1 N 0 1 Y N N -26.832 -27.951 -4.919 -0.382 -0.060 -0.029 N9 6OS 14 6OS N3 N2 N 0 1 Y N N -26.655 -28.578 -2.570 -2.253 -1.066 1.279 N3 6OS 15 6OS N1 N3 N 0 1 Y N N -25.161 -30.361 -2.140 -4.361 -0.349 0.660 N1 6OS 16 6OS C8 C11 C 0 1 Y N N -26.267 -28.439 -6.045 -0.422 0.847 -1.047 C8 6OS 17 6OS N7 N4 N 0 1 Y N N -25.420 -29.460 -5.753 -1.656 1.175 -1.301 N7 6OS 18 6OS N6 N5 N 0 1 N N N -23.938 -31.465 -3.824 -4.721 1.214 -1.068 N6 6OS 19 6OS H1 H1 H 0 1 N N N -26.256 -29.352 -0.677 -3.998 -1.715 2.173 H1 6OS 20 6OS H2 H2 H 0 1 N N N -28.402 -23.160 -6.051 4.562 -0.377 -1.577 H2 6OS 21 6OS H3 H3 H 0 1 N N N -28.469 -25.111 -7.299 2.233 0.144 -1.888 H3 6OS 22 6OS H4 H4 H 0 1 N N N -26.678 -25.889 -6.283 0.937 -1.751 -1.355 H4 6OS 23 6OS H5 H5 H 0 1 N N N -26.044 -25.070 -4.213 2.842 -3.047 -0.599 H5 6OS 24 6OS H6 H6 H 0 1 N N N -31.378 -25.083 -6.799 4.838 1.008 0.349 H6 6OS 25 6OS H7 H7 H 0 1 N N N -31.270 -26.811 -7.275 3.888 2.236 -0.521 H7 6OS 26 6OS H8 H8 H 0 1 N N N -32.957 -26.413 -5.716 4.401 2.924 1.708 H8 6OS 27 6OS H9 H9 H 0 1 N N N -29.791 -28.050 -4.993 1.675 0.967 1.920 H9 6OS 28 6OS H10 H10 H 0 1 N N N -27.879 -26.616 -3.708 0.559 -1.325 1.372 H10 6OS 29 6OS H11 H11 H 0 1 N N N -26.462 -28.068 -7.040 0.442 1.235 -1.565 H11 6OS 30 6OS H12 H12 H 0 1 N N N -23.619 -31.971 -3.022 -4.354 1.796 -1.752 H12 6OS 31 6OS H13 H13 H 0 1 N N N -24.381 -32.096 -4.461 -5.681 1.169 -0.933 H13 6OS 32 # # 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 6OS "C5'" "C4'" SING N N 1 6OS "C5'" "O5'" SING N N 2 6OS "C3'" "C4'" SING N N 3 6OS "C3'" "O3'" SING N N 4 6OS "C3'" "C2'" SING N N 5 6OS C8 N7 DOUB Y N 6 6OS C8 N9 SING Y N 7 6OS "C4'" "C6'" DOUB N N 8 6OS N7 C5 SING Y N 9 6OS "C2'" "C1'" SING N N 10 6OS "C2'" "O2'" SING N N 11 6OS "C6'" "C1'" SING N N 12 6OS N9 "C1'" SING N N 13 6OS N9 C4 SING Y N 14 6OS C5 C4 DOUB Y N 15 6OS C5 C6 SING Y N 16 6OS C4 N3 SING Y N 17 6OS N6 C6 SING N N 18 6OS C6 N1 DOUB Y N 19 6OS N3 C2 DOUB Y N 20 6OS N1 C2 SING Y N 21 6OS C2 H1 SING N N 22 6OS "O3'" H2 SING N N 23 6OS "C3'" H3 SING N N 24 6OS "C2'" H4 SING N N 25 6OS "O2'" H5 SING N N 26 6OS "C5'" H6 SING N N 27 6OS "C5'" H7 SING N N 28 6OS "O5'" H8 SING N N 29 6OS "C6'" H9 SING N N 30 6OS "C1'" H10 SING N N 31 6OS C8 H11 SING N N 32 6OS N6 H12 SING N N 33 6OS N6 H13 SING N N 34 # # 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 6OS SMILES ACDLabs 12.01 "c1nc2c(c(n1)N)ncn2C3C(C(O)C(=C3)CO)O" 6OS InChI InChI 1.03 "InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1" 6OS InChIKey InChI 1.03 XUGWUUDOWNZAGW-VDAHYXPESA-N 6OS SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n(cnc12)[C@@H]3C=C(CO)[C@@H](O)[C@H]3O" 6OS SMILES CACTVS 3.385 "Nc1ncnc2n(cnc12)[CH]3C=C(CO)[CH](O)[CH]3O" 6OS SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1nc(c2c(n1)n(cn2)[C@@H]3C=C([C@H]([C@H]3O)O)CO)N" 6OS SMILES "OpenEye OEToolkits" 2.0.4 "c1nc(c2c(n1)n(cn2)C3C=C(C(C3O)O)CO)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 6OS "SYSTEMATIC NAME" ACDLabs 12.01 "(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol" 6OS "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "(1~{S},2~{R},5~{R})-5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 6OS "Create component" 2016-05-16 RCSB 6OS "Initial release" 2016-05-25 RCSB 6OS "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 6OS _pdbx_chem_comp_synonyms.name "(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##