data_DM9 # _chem_comp.id DM9 _chem_comp.name "N-HYDROXYMETHYL-N-(2-METHOXYETHYL)-DAUNOMYCIN" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C31 H39 N O12" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-30 _chem_comp.pdbx_modified_date 2011-06-04 _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 617.641 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DM9 _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 482D _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 DM9 C1 C1 C 0 1 Y N N 15.566 18.348 5.136 1.521 0.826 -6.498 C1 DM9 1 DM9 C2 C2 C 0 1 Y N N 16.770 19.075 5.151 2.803 0.537 -6.843 C2 DM9 2 DM9 C3 C3 C 0 1 Y N N 18.020 18.424 5.050 3.693 -0.041 -5.940 C3 DM9 3 DM9 C4 C4 C 0 1 Y N N 18.011 17.033 4.940 3.320 -0.346 -4.665 C4 DM9 4 DM9 O4 O4 O 0 1 N N N 19.235 16.401 4.836 4.210 -0.909 -3.807 O4 DM9 5 DM9 C5 C5 C 0 1 Y N N 16.763 14.875 4.847 1.581 -0.369 -2.941 C5 DM9 6 DM9 O5 O5 O 0 1 N N N 17.916 14.159 4.753 2.446 -0.932 -2.057 O5 DM9 7 DM9 C6 C6 C 0 1 Y N N 15.422 12.725 4.783 -0.194 -0.370 -1.255 C6 DM9 8 DM9 O6 O6 O 0 1 N N N 16.593 11.963 4.706 0.646 -0.936 -0.350 O6 DM9 9 DM9 C7 C7 C 0 1 N N S 14.157 10.573 4.716 -1.891 -0.431 0.514 C7 DM9 10 DM9 O7 O7 O 0 1 N N N 14.761 10.203 6.077 -0.838 -0.069 1.410 O7 DM9 11 DM9 C8 C8 C 0 1 N N N 12.806 9.899 4.530 -3.165 0.312 0.909 C8 DM9 12 DM9 C9 C9 C 0 1 N N S 11.695 10.716 5.294 -4.219 0.074 -0.177 C9 DM9 13 DM9 O9 O9 O 0 1 N N N 11.831 10.661 6.722 -5.489 0.554 0.269 O9 DM9 14 DM9 C10 C10 C 0 1 N N N 11.623 12.217 4.872 -3.795 0.832 -1.432 C10 DM9 15 DM9 C11 C11 C 0 1 Y N N 13.073 14.229 4.944 -1.979 0.798 -3.080 C11 DM9 16 DM9 O11 O11 O 0 1 N N N 11.864 14.870 5.026 -2.866 1.362 -3.942 O11 DM9 17 DM9 C12 C12 C 0 1 Y N N 14.326 16.304 5.028 -0.246 0.823 -4.809 C12 DM9 18 DM9 O12 O12 O 0 1 N N N 13.199 16.976 5.103 -1.110 1.387 -5.692 O12 DM9 19 DM9 C13 C13 C 0 1 N N N 10.408 9.987 5.067 -4.312 -1.399 -0.481 C13 DM9 20 DM9 O13 O13 O 0 1 N N N 9.668 10.374 4.059 -3.663 -1.871 -1.382 O13 DM9 21 DM9 C14 C14 C 0 1 N N N 9.977 8.858 5.991 -5.215 -2.282 0.340 C14 DM9 22 DM9 C15 C15 C 0 1 Y N N 15.593 16.965 5.031 1.067 0.537 -5.194 C15 DM9 23 DM9 C16 C16 C 0 1 Y N N 16.810 16.299 4.942 1.999 -0.071 -4.241 C16 DM9 24 DM9 C17 C17 C 0 1 Y N N 15.499 14.146 4.857 0.268 -0.083 -2.556 C17 DM9 25 DM9 C18 C18 C 0 1 Y N N 14.293 14.892 4.943 -0.664 0.524 -3.509 C18 DM9 26 DM9 C19 C19 C 0 1 Y N N 13.003 12.826 4.867 -2.370 0.498 -1.800 C19 DM9 27 DM9 C20 C20 C 0 1 Y N N 14.151 12.061 4.791 -1.486 -0.081 -0.896 C20 DM9 28 DM9 C21 C21 C 0 1 N N N 20.516 17.202 4.836 5.437 -1.057 -4.525 C21 DM9 29 DM9 "C1'" C1* C 0 1 N N R 15.679 9.022 6.190 -0.747 -1.112 2.382 "C1'" DM9 30 DM9 "C2'" C2* C 0 1 N N N 16.526 9.188 7.433 0.576 -0.986 3.141 "C2'" DM9 31 DM9 "C3'" C3* C 0 1 N N S 15.647 8.880 8.676 0.637 0.389 3.813 "C3'" DM9 32 DM9 "C4'" C4* C 0 1 N N S 14.768 7.623 8.553 -0.622 0.579 4.665 "C4'" DM9 33 DM9 "O4'" O4* O 0 1 N N N 15.779 6.531 8.392 -0.609 -0.351 5.749 "O4'" DM9 34 DM9 "C5'" C5* C 0 1 N N S 13.940 7.661 7.218 -1.855 0.331 3.792 "C5'" DM9 35 DM9 "O5'" O5* O 0 1 N N N 14.849 7.861 6.058 -1.838 -1.005 3.295 "O5'" DM9 36 DM9 "C6'" C6* C 0 1 N N N 13.113 6.376 7.039 -3.119 0.547 4.627 "C6'" DM9 37 DM9 "N3'" N3* N 0 1 N N N 16.299 9.159 9.980 1.827 0.466 4.671 "N3'" DM9 38 DM9 C31 C31 C 0 1 N N N 17.752 9.461 9.816 1.870 1.831 5.212 C31 DM9 39 DM9 O31 O31 O 0 1 N N N 18.017 10.926 10.096 1.179 1.870 6.462 O31 DM9 40 DM9 C41 C41 C 0 1 N N N 15.998 8.105 11.049 2.993 0.325 3.788 C41 DM9 41 DM9 C42 C42 C 0 1 N N N 16.857 8.315 12.307 4.275 0.397 4.621 C42 DM9 42 DM9 O42 O42 O 0 1 N N N 17.444 6.968 12.767 4.277 -0.658 5.584 O42 DM9 43 DM9 C43 C43 C 0 1 N N N 17.449 5.736 11.900 5.492 -0.537 6.326 C43 DM9 44 DM9 H1 H1 H 0 1 N N N 14.594 18.865 5.207 0.853 1.274 -7.219 H1 DM9 45 DM9 H2 H2 H 0 1 N N N 16.733 20.173 5.243 3.141 0.761 -7.844 H2 DM9 46 DM9 H3 H3 H 0 1 N N N 18.970 18.982 5.056 4.702 -0.254 -6.259 H3 DM9 47 DM9 HO5 HO5 H 0 1 N N N 17.884 13.211 4.689 2.888 -0.205 -1.598 HO5 DM9 48 DM9 HO6 HO6 H 0 1 N N N 16.541 11.015 4.656 1.117 -0.212 0.084 HO6 DM9 49 DM9 H7 H7 H 0 1 N N N 14.709 10.224 3.812 -2.067 -1.504 0.582 H7 DM9 50 DM9 H81 1H8 H 0 1 N N N 12.554 9.752 3.453 -3.530 -0.065 1.864 H81 DM9 51 DM9 H82 2H8 H 0 1 N N N 12.825 8.827 4.837 -2.956 1.379 0.991 H82 DM9 52 DM9 HO9 HO9 H 0 1 N N N 11.161 11.153 7.182 -6.119 0.384 -0.444 HO9 DM9 53 DM9 H101 1H10 H 0 0 N N N 11.106 12.349 3.892 -4.453 0.559 -2.257 H101 DM9 54 DM9 H102 2H10 H 0 0 N N N 10.915 12.795 5.511 -3.877 1.904 -1.249 H102 DM9 55 DM9 HO11 HO11 H 0 0 N N N 11.029 14.416 5.026 -2.783 2.320 -3.841 HO11 DM9 56 DM9 HO12 HO12 H 0 0 N N N 12.356 16.536 5.101 -1.023 2.345 -5.595 HO12 DM9 57 DM9 H141 1H14 H 0 0 N N N 9.018 8.314 5.821 -5.150 -3.307 -0.023 H141 DM9 58 DM9 H142 2H14 H 0 0 N N N 10.799 8.106 6.027 -4.905 -2.247 1.385 H142 DM9 59 DM9 H143 3H14 H 0 0 N N N 9.976 9.246 7.036 -6.243 -1.930 0.255 H143 DM9 60 DM9 H211 1H21 H 0 0 N N N 21.503 16.691 4.752 6.187 -1.508 -3.874 H211 DM9 61 DM9 H212 2H21 H 0 0 N N N 20.448 17.967 4.028 5.276 -1.698 -5.391 H212 DM9 62 DM9 H213 3H21 H 0 0 N N N 20.529 17.839 5.750 5.785 -0.079 -4.856 H213 DM9 63 DM9 "H1'" H1* H 0 1 N N N 16.449 8.915 5.391 -0.787 -2.079 1.882 "H1'" DM9 64 DM9 "H2'1" 1H2* H 0 0 N N N 17.454 8.571 7.402 1.407 -1.088 2.443 "H2'1" DM9 65 DM9 "H2'2" 2H2* H 0 0 N N N 17.009 10.191 7.489 0.637 -1.766 3.899 "H2'2" DM9 66 DM9 "H3'" H3* H 0 1 N N N 14.855 9.665 8.679 0.684 1.167 3.051 "H3'" DM9 67 DM9 "H4'" H4* H 0 1 N N N 14.064 7.513 9.410 -0.652 1.596 5.057 "H4'" DM9 68 DM9 "HO4'" HO4* H 0 0 N N N 15.236 5.755 8.316 -1.421 -0.204 6.253 "HO4'" DM9 69 DM9 "H5'" H5* H 0 1 N N N 13.229 8.518 7.273 -1.850 1.029 2.955 "H5'" DM9 70 DM9 "H6'1" 1H6* H 0 0 N N N 12.525 6.403 6.091 -3.999 0.379 4.005 "H6'1" DM9 71 DM9 "H6'2" 2H6* H 0 0 N N N 13.753 5.465 7.098 -3.126 -0.152 5.463 "H6'2" DM9 72 DM9 "H6'3" 3H6* H 0 0 N N N 12.459 6.183 7.921 -3.133 1.568 5.007 "H6'3" DM9 73 DM9 H311 1H31 H 0 0 N N N 18.389 8.795 10.443 2.907 2.131 5.361 H311 DM9 74 DM9 H312 2H31 H 0 0 N N N 18.130 9.153 8.813 1.392 2.515 4.511 H312 DM9 75 DM9 HO31 HO31 H 0 0 N N N 18.941 11.118 9.991 1.230 2.781 6.782 HO31 DM9 76 DM9 H411 1H41 H 0 0 N N N 14.911 8.075 11.297 2.992 1.131 3.053 H411 DM9 77 DM9 H412 2H41 H 0 0 N N N 16.111 7.071 10.645 2.947 -0.634 3.275 H412 DM9 78 DM9 H421 1H42 H 0 0 N N N 17.647 9.085 12.151 4.322 1.358 5.134 H421 DM9 79 DM9 H422 2H42 H 0 0 N N N 16.291 8.826 13.120 5.140 0.293 3.966 H422 DM9 80 DM9 H431 1H43 H 0 0 N N N 17.874 4.760 12.233 5.538 -1.326 7.077 H431 DM9 81 DM9 H432 2H43 H 0 0 N N N 16.397 5.549 11.579 6.341 -0.630 5.649 H432 DM9 82 DM9 H433 3H43 H 0 0 N N N 17.946 6.006 10.939 5.523 0.434 6.817 H433 DM9 83 # 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 DM9 C1 C2 DOUB Y N 1 DM9 C1 C15 SING Y N 2 DM9 C1 H1 SING N N 3 DM9 C2 C3 SING Y N 4 DM9 C2 H2 SING N N 5 DM9 C3 C4 DOUB Y N 6 DM9 C3 H3 SING N N 7 DM9 C4 O4 SING N N 8 DM9 C4 C16 SING Y N 9 DM9 O4 C21 SING N N 10 DM9 C5 O5 SING N N 11 DM9 C5 C16 DOUB Y N 12 DM9 C5 C17 SING Y N 13 DM9 O5 HO5 SING N N 14 DM9 C6 O6 SING N N 15 DM9 C6 C17 DOUB Y N 16 DM9 C6 C20 SING Y N 17 DM9 O6 HO6 SING N N 18 DM9 C7 O7 SING N N 19 DM9 C7 C8 SING N N 20 DM9 C7 C20 SING N N 21 DM9 C7 H7 SING N N 22 DM9 O7 "C1'" SING N N 23 DM9 C8 C9 SING N N 24 DM9 C8 H81 SING N N 25 DM9 C8 H82 SING N N 26 DM9 C9 O9 SING N N 27 DM9 C9 C10 SING N N 28 DM9 C9 C13 SING N N 29 DM9 O9 HO9 SING N N 30 DM9 C10 C19 SING N N 31 DM9 C10 H101 SING N N 32 DM9 C10 H102 SING N N 33 DM9 C11 O11 SING N N 34 DM9 C11 C18 DOUB Y N 35 DM9 C11 C19 SING Y N 36 DM9 O11 HO11 SING N N 37 DM9 C12 O12 SING N N 38 DM9 C12 C15 DOUB Y N 39 DM9 C12 C18 SING Y N 40 DM9 O12 HO12 SING N N 41 DM9 C13 O13 DOUB N N 42 DM9 C13 C14 SING N N 43 DM9 C14 H141 SING N N 44 DM9 C14 H142 SING N N 45 DM9 C14 H143 SING N N 46 DM9 C15 C16 SING Y N 47 DM9 C17 C18 SING Y N 48 DM9 C19 C20 DOUB Y N 49 DM9 C21 H211 SING N N 50 DM9 C21 H212 SING N N 51 DM9 C21 H213 SING N N 52 DM9 "C1'" "C2'" SING N N 53 DM9 "C1'" "O5'" SING N N 54 DM9 "C1'" "H1'" SING N N 55 DM9 "C2'" "C3'" SING N N 56 DM9 "C2'" "H2'1" SING N N 57 DM9 "C2'" "H2'2" SING N N 58 DM9 "C3'" "C4'" SING N N 59 DM9 "C3'" "N3'" SING N N 60 DM9 "C3'" "H3'" SING N N 61 DM9 "C4'" "O4'" SING N N 62 DM9 "C4'" "C5'" SING N N 63 DM9 "C4'" "H4'" SING N N 64 DM9 "O4'" "HO4'" SING N N 65 DM9 "C5'" "O5'" SING N N 66 DM9 "C5'" "C6'" SING N N 67 DM9 "C5'" "H5'" SING N N 68 DM9 "C6'" "H6'1" SING N N 69 DM9 "C6'" "H6'2" SING N N 70 DM9 "C6'" "H6'3" SING N N 71 DM9 "N3'" C31 SING N N 72 DM9 "N3'" C41 SING N N 73 DM9 C31 O31 SING N N 74 DM9 C31 H311 SING N N 75 DM9 C31 H312 SING N N 76 DM9 O31 HO31 SING N N 77 DM9 C41 C42 SING N N 78 DM9 C41 H411 SING N N 79 DM9 C41 H412 SING N N 80 DM9 C42 O42 SING N N 81 DM9 C42 H421 SING N N 82 DM9 C42 H422 SING N N 83 DM9 O42 C43 SING N N 84 DM9 C43 H431 SING N N 85 DM9 C43 H432 SING N N 86 DM9 C43 H433 SING N N 87 # 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 DM9 SMILES ACDLabs 10.04 "O=C(C)C5(O)CC(OC1OC(C(O)C(N(CCOC)CO)C1)C)c4c(O)c3c(O)c2c(OC)cccc2c(O)c3c(O)c4C5" DM9 SMILES_CANONICAL CACTVS 3.341 "COCCN(CO)[C@H]1C[C@@H](O[C@@H](C)[C@H]1O)O[C@H]2C[C@@](O)(Cc3c(O)c4c(O)c5cccc(OC)c5c(O)c4c(O)c23)C(C)=O" DM9 SMILES CACTVS 3.341 "COCCN(CO)[CH]1C[CH](O[CH](C)[CH]1O)O[CH]2C[C](O)(Cc3c(O)c4c(O)c5cccc(OC)c5c(O)c4c(O)c23)C(C)=O" DM9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)c(c5cccc(c5c4O)OC)O)O)(C(=O)C)O)[N@@](CCOC)CO)O" DM9 SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3O)c(c5cccc(c5c4O)OC)O)O)(C(=O)C)O)N(CCOC)CO)O" DM9 InChI InChI 1.03 "InChI=1S/C31H39NO12/c1-14-26(35)18(32(13-33)8-9-41-3)10-21(43-14)44-20-12-31(40,15(2)34)11-17-23(20)30(39)25-24(28(17)37)27(36)16-6-5-7-19(42-4)22(16)29(25)38/h5-7,14,18,20-21,26,33,35-40H,8-13H2,1-4H3/t14-,18-,20-,21-,26+,31-/m0/s1" DM9 InChIKey InChI 1.03 IURHBLXSEHXXFF-XGGCRALDSA-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 DM9 "SYSTEMATIC NAME" ACDLabs 10.04 "(1S,3S)-3-acetyl-3,5,6,11,12-pentahydroxy-10-methoxy-1,2,3,4-tetrahydrotetracen-1-yl 2,3,6-trideoxy-3-[(hydroxymethyl)(2-methoxyethyl)amino]-alpha-L-lyxo-hexopyranoside" DM9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "1-[(2S,4S)-2,5,6,11,12-pentahydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-(hydroxymethyl-(2-methoxyethyl)amino)-6-methyl-oxan-2-yl]oxy-7-methoxy-3,4-dihydro-1H-tetracen-2-yl]ethanone" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DM9 "Create component" 1999-07-30 RCSB DM9 "Modify descriptor" 2011-06-04 RCSB #