data_DM8 # _chem_comp.id DM8 _chem_comp.name "2'-BROMO-4'-EPIDAUNORUBICIN" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C27 H28 Br N O10" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "WP401; DAUNOMYCIN DERIVATIVE; DAUNORUBICIN DERIVATIVE" _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 606.416 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DM8 _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 288D _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 DM8 C1 C1 C 0 1 Y N N 15.274 18.233 5.160 0.065 0.259 -6.672 C1 DM8 1 DM8 C2 C2 C 0 1 Y N N 16.433 18.990 5.192 1.231 -0.077 -7.342 C2 DM8 2 DM8 C3 C3 C 0 1 Y N N 17.770 18.382 5.139 2.396 -0.319 -6.644 C3 DM8 3 DM8 C4 C4 C 0 1 Y N N 17.843 16.929 5.032 2.418 -0.229 -5.255 C4 DM8 4 DM8 C5 C5 C 0 1 N N N 16.674 14.730 4.915 1.248 0.210 -3.095 C5 DM8 5 DM8 C6 C6 C 0 1 Y N N 15.426 12.608 4.888 -0.100 0.070 -1.002 C6 DM8 6 DM8 C7 C7 C 0 1 N N S 14.139 10.412 4.808 -1.314 -0.107 1.158 C7 DM8 7 DM8 C8 C8 C 0 1 N N N 12.801 9.789 4.728 -2.609 0.393 1.793 C8 DM8 8 DM8 C9 C9 C 0 1 N N S 11.663 10.538 5.336 -3.789 -0.207 1.020 C9 DM8 9 DM8 C10 C10 C 0 1 N N N 11.604 12.036 4.877 -3.835 0.438 -0.362 C10 DM8 10 DM8 C11 C11 C 0 1 Y N N 12.975 14.015 4.941 -2.441 0.559 -2.416 C11 DM8 11 DM8 C12 C12 C 0 1 N N N 14.125 16.183 5.059 -1.171 0.712 -4.556 C12 DM8 12 DM8 C13 C13 C 0 1 N N N 10.342 9.899 4.963 -3.600 -1.696 0.880 C13 DM8 13 DM8 C14 C14 C 0 1 N N N 10.005 8.931 5.801 -4.053 -2.620 1.980 C14 DM8 14 DM8 C15 C15 C 0 1 Y N N 15.409 16.834 5.075 0.064 0.354 -5.286 C15 DM8 15 DM8 C16 C16 C 0 1 Y N N 16.626 16.234 5.000 1.249 0.103 -4.567 C16 DM8 16 DM8 C17 C17 C 0 1 Y N N 15.398 14.004 4.947 -0.039 0.263 -2.379 C17 DM8 17 DM8 C18 C18 C 0 1 Y N N 14.122 14.753 4.963 -1.228 0.509 -3.097 C18 DM8 18 DM8 C19 C19 C 0 1 Y N N 12.913 12.616 4.899 -2.485 0.363 -1.029 C19 DM8 19 DM8 C20 C20 C 0 1 Y N N 14.147 11.988 4.851 -1.329 0.119 -0.331 C20 DM8 20 DM8 C21 C21 C 0 1 N N N 20.319 16.808 5.011 4.565 -0.784 -5.546 C21 DM8 21 DM8 O4 O4 O 0 1 N N N 19.021 16.304 4.995 3.566 -0.468 -4.574 O4 DM8 22 DM8 O5 O5 O 0 1 N N N 17.711 14.049 4.856 2.296 0.249 -2.479 O5 DM8 23 DM8 O6 O6 O 0 1 N N N 16.522 11.918 4.845 1.038 -0.167 -0.305 O6 DM8 24 DM8 O7 O7 O 0 1 N N N 14.812 10.154 6.083 -0.207 0.594 1.729 O7 DM8 25 DM8 O9 O9 O 0 1 N N N 11.685 10.527 6.814 -5.007 0.059 1.717 O9 DM8 26 DM8 O11 O11 O 0 1 N N N 11.778 14.756 5.000 -3.588 0.799 -3.098 O11 DM8 27 DM8 O12 O12 O 0 1 N N N 13.090 16.892 5.080 -2.128 1.167 -5.153 O12 DM8 28 DM8 O13 O13 O 0 1 N N N 9.358 10.261 3.922 -3.085 -2.148 -0.114 O13 DM8 29 DM8 "C1'" C1* C 0 1 N N R 15.734 9.125 6.217 0.516 -0.349 2.520 "C1'" DM8 30 DM8 "C2'" C2* C 0 1 N N R 16.374 9.178 7.631 1.874 0.243 2.903 "C2'" DM8 31 DM8 "C3'" C3* C 0 1 N N R 15.317 8.898 8.650 1.651 1.543 3.681 "C3'" DM8 32 DM8 "C4'" C4* C 0 1 N N R 14.669 7.490 8.437 0.711 1.255 4.857 "C4'" DM8 33 DM8 "C5'" C5* C 0 1 N N S 13.895 7.563 7.065 -0.559 0.586 4.327 "C5'" DM8 34 DM8 "C6'" C6* C 0 1 N N N 13.306 6.228 6.622 -1.518 0.325 5.491 "C6'" DM8 35 DM8 "O5'" O5* O 0 1 N N N 14.958 7.857 6.030 -0.228 -0.650 3.699 "O5'" DM8 36 DM8 "O4'" O4* O 0 1 N N N 13.738 7.215 9.515 0.369 2.479 5.510 "O4'" DM8 37 DM8 "N3'" N3* N 0 1 N N N 15.872 8.945 10.107 2.935 2.045 4.189 "N3'" DM8 38 DM8 BR BR BR 0 0 N N N 17.849 8.110 7.610 2.859 -1.034 4.027 BR DM8 39 DM8 H1 H1 H 0 1 N N N 14.286 18.722 5.200 -0.841 0.448 -7.227 H1 DM8 40 DM8 H2 H2 H 0 1 N N N 16.290 20.081 5.260 1.227 -0.150 -8.419 H2 DM8 41 DM8 H3 H3 H 0 1 N N N 18.686 18.994 5.178 3.298 -0.580 -7.179 H3 DM8 42 DM8 H7 H7 H 0 1 N N N 14.614 9.978 3.897 -1.204 -1.173 1.358 H7 DM8 43 DM8 H81 1H8 H 0 1 N N N 12.564 9.554 3.663 -2.649 1.480 1.737 H81 DM8 44 DM8 H82 2H8 H 0 1 N N N 12.843 8.762 5.161 -2.653 0.076 2.835 H82 DM8 45 DM8 H101 1H10 H 0 0 N N N 11.117 12.146 3.879 -4.128 1.483 -0.260 H101 DM8 46 DM8 H102 2H10 H 0 0 N N N 10.877 12.627 5.481 -4.569 -0.082 -0.977 H102 DM8 47 DM8 H141 1H14 H 0 0 N N N 9.032 8.460 5.526 -3.835 -3.651 1.701 H141 DM8 48 DM8 H142 2H14 H 0 0 N N N 10.814 8.168 5.884 -3.526 -2.374 2.902 H142 DM8 49 DM8 H143 3H14 H 0 0 N N N 9.995 9.293 6.855 -5.126 -2.504 2.133 H143 DM8 50 DM8 H211 1H21 H 0 0 N N N 21.303 16.285 4.980 5.510 -0.985 -5.043 H211 DM8 51 DM8 H212 2H21 H 0 0 N N N 20.353 17.532 4.164 4.258 -1.666 -6.109 H212 DM8 52 DM8 H213 3H21 H 0 0 N N N 20.364 17.448 5.922 4.687 0.056 -6.228 H213 DM8 53 DM8 H6 H6 H 0 1 N N N 16.541 10.969 4.804 1.139 -1.127 -0.253 H6 DM8 54 DM8 H9 H9 H 0 1 N N N 10.960 11.003 7.201 -5.722 -0.319 1.187 H9 DM8 55 DM8 H11 H11 H 0 1 N N N 10.979 14.242 4.984 -3.936 -0.061 -3.371 H11 DM8 56 DM8 "H1'" H1* H 0 1 N N N 16.562 9.201 5.475 0.669 -1.263 1.945 "H1'" DM8 57 DM8 "H2'" H2* H 0 1 N N N 16.758 10.181 7.929 2.447 0.452 2.000 "H2'" DM8 58 DM8 "H3'" H3* H 0 1 N N N 14.554 9.700 8.513 1.200 2.289 3.027 "H3'" DM8 59 DM8 "H4'" H4* H 0 1 N N N 15.436 6.681 8.427 1.205 0.589 5.565 "H4'" DM8 60 DM8 "H5'" H5* H 0 1 N N N 13.070 8.305 7.172 -1.039 1.243 3.603 "H5'" DM8 61 DM8 "H6'1" 1H6* H 0 0 N N N 12.758 6.279 5.651 -2.425 -0.146 5.115 "H6'1" DM8 62 DM8 "H6'2" 2H6* H 0 0 N N N 14.095 5.441 6.586 -1.039 -0.334 6.215 "H6'2" DM8 63 DM8 "H6'3" 3H6* H 0 0 N N N 12.653 5.801 7.419 -1.771 1.269 5.972 "H6'3" DM8 64 DM8 "HO4'" *HO4 H 0 0 N N N 13.344 6.360 9.385 -0.226 2.252 6.237 "HO4'" DM8 65 DM8 "HN'1" 1HN* H 0 0 N N N 15.150 8.753 10.802 3.517 2.219 3.383 "HN'1" DM8 66 DM8 "HN'2" 2HN* H 0 0 N N N 16.338 9.832 10.294 2.749 2.942 4.612 "HN'2" DM8 67 # # 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 DM8 C1 C2 DOUB Y N 1 DM8 C1 C15 SING Y N 2 DM8 C1 H1 SING N N 3 DM8 C2 C3 SING Y N 4 DM8 C2 H2 SING N N 5 DM8 C3 C4 DOUB Y N 6 DM8 C3 H3 SING N N 7 DM8 C4 C16 SING Y N 8 DM8 C4 O4 SING N N 9 DM8 C5 C16 SING N N 10 DM8 C5 C17 SING N N 11 DM8 C5 O5 DOUB N N 12 DM8 C6 C17 DOUB Y N 13 DM8 C6 C20 SING Y N 14 DM8 C6 O6 SING N N 15 DM8 C7 C8 SING N N 16 DM8 C7 C20 SING N N 17 DM8 C7 O7 SING N N 18 DM8 C7 H7 SING N N 19 DM8 C8 C9 SING N N 20 DM8 C8 H81 SING N N 21 DM8 C8 H82 SING N N 22 DM8 C9 C10 SING N N 23 DM8 C9 C13 SING N N 24 DM8 C9 O9 SING N N 25 DM8 C10 C19 SING N N 26 DM8 C10 H101 SING N N 27 DM8 C10 H102 SING N N 28 DM8 C11 C18 DOUB Y N 29 DM8 C11 C19 SING Y N 30 DM8 C11 O11 SING N N 31 DM8 C12 C15 SING N N 32 DM8 C12 C18 SING N N 33 DM8 C12 O12 DOUB N N 34 DM8 C13 C14 SING N N 35 DM8 C13 O13 DOUB N N 36 DM8 C14 H141 SING N N 37 DM8 C14 H142 SING N N 38 DM8 C14 H143 SING N N 39 DM8 C15 C16 DOUB Y N 40 DM8 C17 C18 SING Y N 41 DM8 C19 C20 DOUB Y N 42 DM8 C21 O4 SING N N 43 DM8 C21 H211 SING N N 44 DM8 C21 H212 SING N N 45 DM8 C21 H213 SING N N 46 DM8 O6 H6 SING N N 47 DM8 O7 "C1'" SING N N 48 DM8 O9 H9 SING N N 49 DM8 O11 H11 SING N N 50 DM8 "C1'" "C2'" SING N N 51 DM8 "C1'" "O5'" SING N N 52 DM8 "C1'" "H1'" SING N N 53 DM8 "C2'" "C3'" SING N N 54 DM8 "C2'" BR SING N N 55 DM8 "C2'" "H2'" SING N N 56 DM8 "C3'" "C4'" SING N N 57 DM8 "C3'" "N3'" SING N N 58 DM8 "C3'" "H3'" SING N N 59 DM8 "C4'" "C5'" SING N N 60 DM8 "C4'" "O4'" SING N N 61 DM8 "C4'" "H4'" SING N N 62 DM8 "C5'" "C6'" SING N N 63 DM8 "C5'" "O5'" SING N N 64 DM8 "C5'" "H5'" SING N N 65 DM8 "C6'" "H6'1" SING N N 66 DM8 "C6'" "H6'2" SING N N 67 DM8 "C6'" "H6'3" SING N N 68 DM8 "O4'" "HO4'" SING N N 69 DM8 "N3'" "HN'1" SING N N 70 DM8 "N3'" "HN'2" SING N N 71 # # 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 DM8 SMILES ACDLabs 10.04 "O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)C)CC5OC4OC(C(O)C(N)C4Br)C" DM8 SMILES_CANONICAL CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](N)[C@H]5Br)c4c(O)c3C(=O)c12)C(C)=O" DM8 SMILES CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5O[CH](C)[CH](O)[CH](N)[CH]5Br)c4c(O)c3C(=O)c12)C(C)=O" DM8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)Br)N)O" DM8 SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(C(C(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)Br)N)O" DM8 InChI InChI 1.03 "InChI=1S/C27H28BrNO10/c1-9-21(31)20(29)19(28)26(38-9)39-14-8-27(36,10(2)30)7-12-16(14)25(35)18-17(23(12)33)22(32)11-5-4-6-13(37-3)15(11)24(18)34/h4-6,9,14,19-21,26,31,33,35-36H,7-8,29H2,1-3H3/t9-,14-,19+,20-,21-,26-,27-/m0/s1" DM8 InChIKey InChI 1.03 RNTSDANIDLGPLQ-VQBVCDDFSA-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 DM8 "SYSTEMATIC NAME" ACDLabs 10.04 "(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2-bromo-2,3,6-trideoxy-alpha-L-mannopyranoside" DM8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(7S,9S)-7-[(2R,3R,4R,5R,6S)-4-amino-3-bromo-5-hydroxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DM8 "Create component" 1999-07-08 RCSB DM8 "Modify descriptor" 2011-06-04 RCSB DM8 "Modify synonyms" 2020-06-05 PDBE # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 DM8 WP401 ? ? 2 DM8 "DAUNOMYCIN DERIVATIVE" ? ? 3 DM8 "DAUNORUBICIN DERIVATIVE" ? ? ##