data_DSI # _chem_comp.id DSI _chem_comp.name "4-HYDROXY-6-(1H-INDOLE-2-CARBONYL)-8-METHYL-3,6,7,8-TETRAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C22 H19 N3 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(+)DUOCARMYCIN SA-INDOLE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2020-06-17 _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 389.404 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DSI _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 1DSI _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 DSI C20 C20 C 0 1 Y N N -0.433 0.204 3.012 0.468 -0.071 -5.755 C20 DSI 1 DSI C21 C21 C 0 1 Y N N -0.709 0.284 1.616 -0.833 0.088 -5.239 C21 DSI 2 DSI C22 C22 C 0 1 Y N N 0.266 0.004 0.647 -1.914 0.133 -6.114 C22 DSI 3 DSI C23 C23 C 0 1 Y N N 1.552 -0.382 1.058 -1.703 0.022 -7.471 C23 DSI 4 DSI C25 C25 C 0 1 Y N N 0.878 -0.158 3.392 0.656 -0.182 -7.139 C25 DSI 5 DSI C24 C24 C 0 1 Y N N 1.854 -0.468 2.427 -0.419 -0.135 -7.976 C24 DSI 6 DSI C18 C18 C 0 1 Y N N -2.618 0.822 2.771 0.607 0.065 -3.522 C18 DSI 7 DSI C19 C19 C 0 1 Y N N -1.650 0.526 3.737 1.352 -0.076 -4.650 C19 DSI 8 DSI N17 N17 N 0 1 Y N N -2.042 0.647 1.522 -0.725 0.169 -3.871 N17 DSI 9 DSI C16 C16 C 0 1 N N N -4.038 1.198 2.911 1.135 0.106 -2.151 C16 DSI 10 DSI O16 O16 O 0 1 N N N -4.752 1.188 1.909 2.336 0.110 -1.962 O16 DSI 11 DSI C6 C6 C 0 1 Y N N -8.381 1.581 4.410 2.151 -0.066 2.150 C6 DSI 12 DSI C7 C7 C 0 1 Y N N -7.142 1.341 3.797 1.960 -0.020 0.787 C7 DSI 13 DSI O6 O6 O 0 1 N N N -9.557 1.244 3.806 3.409 -0.166 2.656 O6 DSI 14 DSI C8 C8 C 0 1 Y N N -5.958 1.749 4.456 0.671 0.081 0.241 C8 DSI 15 DSI N12 N12 N 0 1 N N N -4.621 1.590 4.120 0.287 0.140 -1.103 N12 DSI 16 DSI C11 C11 C 0 1 N N N -3.806 1.993 5.303 -1.170 0.243 -1.205 C11 DSI 17 DSI C10 C10 C 0 1 N N S -4.687 2.834 6.225 -1.673 0.244 0.247 C10 DSI 18 DSI C13 C13 C 0 1 N N N -4.603 4.342 5.926 -2.587 -0.957 0.496 C13 DSI 19 DSI C9 C9 C 0 1 Y N N -5.992 2.408 5.663 -0.417 0.137 1.083 C9 DSI 20 DSI C5 C5 C 0 1 Y N N -8.415 2.233 5.660 1.054 -0.011 3.013 C5 DSI 21 DSI C4 C4 C 0 1 Y N N -7.202 2.644 6.283 -0.240 0.091 2.474 C4 DSI 22 DSI C3 C3 C 0 1 Y N N -7.558 3.289 7.542 -1.141 0.122 3.566 C3 DSI 23 DSI C2 C2 C 0 1 Y N N -8.949 3.241 7.627 -0.408 0.049 4.710 C2 DSI 24 DSI N1 N1 N 0 1 Y N N -9.450 2.609 6.502 0.930 -0.035 4.384 N1 DSI 25 DSI C14 C14 C 0 1 N N N -9.778 3.757 8.714 -0.955 0.053 6.073 C14 DSI 26 DSI O15 O15 O 0 1 N N N -11.128 3.464 8.580 -0.125 -0.029 7.132 O15 DSI 27 DSI O14 O14 O 0 1 N N N -9.368 4.402 9.681 -2.156 0.132 6.246 O14 DSI 28 DSI C15 C15 C 0 1 N N N -11.959 3.677 9.708 -0.666 -0.025 8.480 C15 DSI 29 DSI H22 H22 H 0 1 N N N 0.025 0.072 -0.403 -2.916 0.255 -5.731 H22 DSI 30 DSI H23 H23 H 0 1 N N N 2.308 -0.611 0.321 -2.544 0.058 -8.147 H23 DSI 31 DSI H25 H25 H 0 1 N N N 1.130 -0.211 4.439 1.651 -0.305 -7.541 H25 DSI 32 DSI H24 H24 H 0 1 N N N 2.844 -0.764 2.742 -0.271 -0.221 -9.043 H24 DSI 33 DSI H19 H19 H 0 1 N N N -1.800 0.521 4.799 2.427 -0.176 -4.694 H19 DSI 34 DSI H17 H17 H 0 1 N N N -2.572 0.789 0.674 -1.464 0.282 -3.252 H17 DSI 35 DSI H7 H7 H 0 1 N N N -7.104 0.825 2.850 2.815 -0.063 0.128 H7 DSI 36 DSI H6 H6 H 0 1 N N N -10.332 1.564 4.269 3.603 -1.110 2.738 H6 DSI 37 DSI H111 1H11 H 0 0 N N N -2.922 2.564 5.021 -1.450 1.172 -1.703 H111 DSI 38 DSI H112 2H11 H 0 0 N N N -3.537 1.098 5.863 -1.574 -0.612 -1.745 H112 DSI 39 DSI H10 H10 H 0 1 N N N -4.565 2.583 7.273 -2.198 1.173 0.467 H10 DSI 40 DSI H131 1H13 H 0 0 N N N -4.495 4.431 4.855 -3.456 -0.893 -0.157 H131 DSI 41 DSI H132 2H13 H 0 0 N N N -5.544 4.809 6.200 -2.042 -1.878 0.287 H132 DSI 42 DSI H133 3H13 H 0 0 N N N -4.835 4.549 4.855 -2.913 -0.956 1.536 H133 DSI 43 DSI H3 H3 H 0 1 N N N -6.929 3.727 8.302 -2.217 0.192 3.502 H3 DSI 44 DSI H1 H1 H 0 1 N N N -10.442 2.480 6.374 1.663 -0.102 5.017 H1 DSI 45 DSI H151 1H15 H 0 0 N N N -12.979 3.391 9.450 0.150 -0.099 9.199 H151 DSI 46 DSI H152 2H15 H 0 0 N N N -11.956 4.728 10.003 -1.215 0.900 8.648 H152 DSI 47 DSI H153 3H15 H 0 0 N N N -11.623 3.063 10.544 -1.338 -0.874 8.605 H153 DSI 48 # # 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 DSI C20 C21 DOUB Y N 1 DSI C20 C25 SING Y N 2 DSI C20 C19 SING Y N 3 DSI C21 C22 SING Y N 4 DSI C21 N17 SING Y N 5 DSI C22 C23 DOUB Y N 6 DSI C22 H22 SING N N 7 DSI C23 C24 SING Y N 8 DSI C23 H23 SING N N 9 DSI C25 C24 DOUB Y N 10 DSI C25 H25 SING N N 11 DSI C24 H24 SING N N 12 DSI C18 C19 DOUB Y N 13 DSI C18 N17 SING Y N 14 DSI C18 C16 SING N N 15 DSI C19 H19 SING N N 16 DSI N17 H17 SING N N 17 DSI C16 O16 DOUB N N 18 DSI C16 N12 SING N N 19 DSI C6 C7 DOUB Y N 20 DSI C6 O6 SING N N 21 DSI C6 C5 SING Y N 22 DSI C7 C8 SING Y N 23 DSI C7 H7 SING N N 24 DSI O6 H6 SING N N 25 DSI C8 N12 SING N N 26 DSI C8 C9 DOUB Y N 27 DSI N12 C11 SING N N 28 DSI C11 C10 SING N N 29 DSI C11 H111 SING N N 30 DSI C11 H112 SING N N 31 DSI C10 C13 SING N N 32 DSI C10 C9 SING N N 33 DSI C10 H10 SING N N 34 DSI C13 H131 SING N N 35 DSI C13 H132 SING N N 36 DSI C13 H133 SING N N 37 DSI C9 C4 SING Y N 38 DSI C5 C4 DOUB Y N 39 DSI C5 N1 SING Y N 40 DSI C4 C3 SING Y N 41 DSI C3 C2 DOUB Y N 42 DSI C3 H3 SING N N 43 DSI C2 N1 SING Y N 44 DSI C2 C14 SING N N 45 DSI N1 H1 SING N N 46 DSI C14 O15 SING N N 47 DSI C14 O14 DOUB N N 48 DSI O15 C15 SING N N 49 DSI C15 H151 SING N N 50 DSI C15 H152 SING N N 51 DSI C15 H153 SING N N 52 # # 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 DSI SMILES ACDLabs 10.04 "O=C(OC)c2nc1c(O)cc3c(c1c2)C(CN3C(=O)c5cc4ccccc4n5)C" DSI SMILES_CANONICAL CACTVS 3.341 "COC(=O)c1[nH]c2c(O)cc3N(C[C@@H](C)c3c2c1)C(=O)c4[nH]c5ccccc5c4" DSI SMILES CACTVS 3.341 "COC(=O)c1[nH]c2c(O)cc3N(C[CH](C)c3c2c1)C(=O)c4[nH]c5ccccc5c4" DSI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1CN(c2c1c3cc([nH]c3c(c2)O)C(=O)OC)C(=O)c4cc5ccccc5[nH]4" DSI SMILES "OpenEye OEToolkits" 1.5.0 "CC1CN(c2c1c3cc([nH]c3c(c2)O)C(=O)OC)C(=O)c4cc5ccccc5[nH]4" DSI InChI InChI 1.03 "InChI=1S/C22H19N3O4/c1-11-10-25(21(27)15-7-12-5-3-4-6-14(12)23-15)17-9-18(26)20-13(19(11)17)8-16(24-20)22(28)29-2/h3-9,11,23-24,26H,10H2,1-2H3/t11-/m1/s1" DSI InChIKey InChI 1.03 SVXVQSGKGYZESS-LLVKDONJSA-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 DSI "SYSTEMATIC NAME" ACDLabs 10.04 "methyl (8S)-4-hydroxy-6-(1H-indol-2-ylcarbonyl)-8-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate" DSI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (8S)-4-hydroxy-6-(1H-indol-2-ylcarbonyl)-8-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DSI "Create component" 1999-07-08 RCSB DSI "Modify descriptor" 2011-06-04 RCSB DSI "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id DSI _pdbx_chem_comp_synonyms.name "(+)DUOCARMYCIN SA-INDOLE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##