data_CMD # _chem_comp.id CMD _chem_comp.name "3'-DESAMINO-3'-(3-CYANO-4-MORPHOLINYL)-DOXORUBICIN" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C32 H34 N2 O12" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 638.619 _chem_comp.one_letter_code ? _chem_comp.three_letter_code CMD _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 236D _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 CMD C1 C1 C 0 1 Y N N 15.466 18.321 5.079 1.233 -0.769 6.726 C1 CMD 1 CMD C2 C2 C 0 1 Y N N 16.658 19.042 5.036 2.333 -0.139 7.287 C2 CMD 2 CMD C3 C3 C 0 1 Y N N 17.952 18.377 4.956 3.197 0.596 6.503 C3 CMD 3 CMD C4 C4 C 0 1 Y N N 17.974 16.909 4.866 2.975 0.718 5.134 C4 CMD 4 CMD O4 O4 O 0 1 N N N 19.099 16.196 4.775 3.827 1.443 4.367 O4 CMD 5 CMD C5 C5 C 0 1 Y N N 16.711 16.272 4.892 1.868 0.093 4.555 C5 CMD 6 CMD C6 C6 C 0 1 N N N 16.655 14.781 4.839 1.615 0.203 3.106 C6 CMD 7 CMD O6 O6 O 0 1 N N N 17.642 14.051 4.743 2.478 0.627 2.360 O6 CMD 8 CMD C7 C7 C 0 1 Y N N 15.330 14.104 4.882 0.301 -0.200 2.573 C7 CMD 9 CMD C8 C8 C 0 1 Y N N 15.288 12.703 4.818 -0.085 0.151 1.283 C8 CMD 10 CMD O8 O8 O 0 1 N N N 16.354 11.962 4.738 0.755 0.874 0.502 O8 CMD 11 CMD C9 C9 C 0 1 Y N N 14.023 12.081 4.828 -1.338 -0.234 0.787 C9 CMD 12 CMD C10 C10 C 0 1 N N S 14.034 10.499 4.738 -1.688 0.192 -0.615 C10 CMD 13 CMD O10 O10 O 0 1 N N N 14.817 10.127 5.901 -0.547 0.017 -1.458 O10 CMD 14 CMD C11 C11 C 0 1 N N N 12.670 9.885 4.674 -2.847 -0.639 -1.159 C11 CMD 15 CMD C12 C12 C 0 1 N N S 11.621 10.632 5.442 -3.984 -0.613 -0.130 C12 CMD 16 CMD O12 O12 O 0 1 N N N 11.790 10.488 6.866 -5.160 -1.193 -0.697 O12 CMD 17 CMD C13 C13 C 0 1 N N N 10.229 10.009 5.159 -4.266 0.809 0.279 C13 CMD 18 CMD O13 O13 O 0 1 N N N 9.874 10.409 4.049 -3.749 1.266 1.270 O13 CMD 19 CMD C14 C14 C 0 1 N N N 9.854 8.577 5.554 -5.192 1.662 -0.548 C14 CMD 20 CMD O14 O14 O 0 1 N N N 8.414 8.290 5.655 -5.298 2.960 0.040 O14 CMD 21 CMD C15 C15 C 0 1 N N N 11.503 12.134 4.983 -3.547 -1.422 1.088 C15 CMD 22 CMD C16 C16 C 0 1 Y N N 12.802 12.746 4.935 -2.192 -0.969 1.569 C16 CMD 23 CMD C17 C17 C 0 1 Y N N 12.884 14.152 4.994 -1.818 -1.332 2.870 C17 CMD 24 CMD O17 O17 O 0 1 N N N 11.731 14.919 5.095 -2.668 -2.057 3.638 O17 CMD 25 CMD C18 C18 C 0 1 Y N N 14.073 14.888 4.999 -0.578 -0.952 3.379 C18 CMD 26 CMD C19 C19 C 0 1 N N N 14.180 16.325 5.047 -0.176 -1.326 4.747 C19 CMD 27 CMD O19 O19 O 0 1 N N N 13.197 17.047 5.154 -0.797 -2.171 5.363 O19 CMD 28 CMD C20 C20 C 0 1 Y N N 15.516 16.920 5.010 0.993 -0.661 5.361 C20 CMD 29 CMD C21 C21 C 0 1 N N N 20.398 17.007 4.770 4.838 1.951 5.240 C21 CMD 30 CMD "C1'" C1* C 0 1 N N R 15.553 8.966 5.975 -0.371 1.240 -2.175 "C1'" CMD 31 CMD "C2'" C2* C 0 1 N N N 16.585 9.014 7.064 1.006 1.247 -2.841 "C2'" CMD 32 CMD "C3'" C3* C 0 1 N N S 15.860 9.166 8.424 1.109 0.045 -3.787 "C3'" CMD 33 CMD "C4'" C4* C 0 1 N N S 14.896 7.960 8.590 -0.081 0.077 -4.751 "C4'" CMD 34 CMD "O4'" O4* O 0 1 N N N 15.739 6.770 8.723 0.024 1.219 -5.604 "O4'" CMD 35 CMD "C5'" C5* C 0 1 N N S 13.882 7.940 7.475 -1.377 0.159 -3.941 "C5'" CMD 36 CMD "O5'" O5* O 0 1 N N N 14.600 7.850 6.141 -1.387 1.357 -3.169 "O5'" CMD 37 CMD "C6'" C6* C 0 1 N N N 13.011 6.655 7.459 -2.574 0.159 -4.894 "C6'" CMD 38 CMD "N3'" N3* N 0 1 N N N 16.869 9.163 9.534 2.364 0.122 -4.546 "N3'" CMD 39 CMD C33 C33 C 0 1 N N S 16.156 9.076 10.761 2.679 -1.245 -4.981 C33 CMD 40 CMD C23 C23 C 0 1 N N N 16.669 10.113 11.839 4.063 -1.269 -5.630 C23 CMD 41 CMD O16 O16 O 0 1 N N N 18.129 10.017 11.753 5.052 -0.900 -4.670 O16 CMD 42 CMD C63 C63 C 0 1 N N N 18.631 10.626 10.542 4.777 0.443 -4.276 C63 CMD 43 CMD C53 C53 C 0 1 N N N 17.763 10.263 9.337 3.411 0.511 -3.592 C53 CMD 44 CMD C73 C73 C 0 1 N N N 16.432 7.672 11.305 1.671 -1.692 -5.957 C73 CMD 45 CMD N73 N73 N 0 1 N N N 17.286 7.055 11.839 0.894 -2.038 -6.710 N73 CMD 46 CMD H1 H1 H 0 1 N N N 14.501 18.849 5.166 0.564 -1.344 7.348 H1 CMD 47 CMD H2 H2 H 0 1 N N N 16.577 20.141 5.065 2.515 -0.226 8.348 H2 CMD 48 CMD H3 H3 H 0 1 N N N 18.884 18.965 4.963 4.050 1.081 6.954 H3 CMD 49 CMD HO8 HO8 H 0 1 N N N 16.325 11.013 4.694 0.612 1.804 0.724 HO8 CMD 50 CMD H10 H10 H 0 1 N N N 14.473 10.113 3.788 -1.972 1.244 -0.610 H10 CMD 51 CMD H111 1H11 H 0 0 N N N 12.353 9.748 3.613 -2.519 -1.667 -1.317 H111 CMD 52 CMD H112 2H11 H 0 0 N N N 12.706 8.819 5.000 -3.194 -0.215 -2.101 H112 CMD 53 CMD HO12 2HO1 H 0 0 N N N 11.125 10.961 7.352 -5.841 -1.171 -0.011 HO12 CMD 54 CMD H141 1H14 H 0 0 N N N 10.335 7.853 4.855 -4.796 1.753 -1.559 H141 CMD 55 CMD H142 2H14 H 0 0 N N N 10.361 8.302 6.508 -6.178 1.198 -0.584 H142 CMD 56 CMD HO14 4HO1 H 0 0 N N N 8.181 7.402 5.899 -5.898 3.472 -0.518 HO14 CMD 57 CMD H151 1H15 H 0 0 N N N 10.962 12.230 4.012 -3.498 -2.478 0.819 H151 CMD 58 CMD H152 2H15 H 0 0 N N N 10.795 12.710 5.624 -4.275 -1.289 1.887 H152 CMD 59 CMD HO17 7HO1 H 0 0 N N N 11.786 15.866 5.134 -3.216 -1.424 4.122 HO17 CMD 60 CMD H211 1H21 H 0 0 N N N 21.337 16.411 4.694 5.549 2.544 4.666 H211 CMD 61 CMD H212 2H21 H 0 0 N N N 20.365 17.772 3.960 4.377 2.577 6.004 H212 CMD 62 CMD H213 3H21 H 0 0 N N N 20.437 17.668 5.666 5.358 1.120 5.716 H213 CMD 63 CMD "H1'" H1* H 0 1 N N N 16.141 8.823 5.038 -0.443 2.079 -1.483 "H1'" CMD 64 CMD "H2'1" 1H2* H 0 0 N N N 17.271 8.135 7.041 1.133 2.169 -3.407 "H2'1" CMD 65 CMD "H2'2" 2H2* H 0 0 N N N 17.348 9.809 6.895 1.780 1.176 -2.077 "H2'2" CMD 66 CMD "H3'" H3* H 0 1 N N N 15.291 10.124 8.458 1.087 -0.878 -3.209 "H3'" CMD 67 CMD "H4'" H4* H 0 1 N N N 14.261 8.019 9.505 -0.086 -0.829 -5.356 "H4'" CMD 68 CMD "HO4'" *HO4 H 0 0 N N N 15.149 6.032 8.824 -0.742 1.200 -6.193 "HO4'" CMD 69 CMD "H5'" H5* H 0 1 N N N 13.268 8.857 7.632 -1.443 -0.701 -3.276 "H5'" CMD 70 CMD "H6'1" 1H6* H 0 0 N N N 12.260 6.640 6.634 -3.497 0.218 -4.318 "H6'1" CMD 71 CMD "H6'2" 2H6* H 0 0 N N N 13.651 5.742 7.427 -2.507 1.019 -5.562 "H6'2" CMD 72 CMD "H6'3" 3H6* H 0 0 N N N 12.516 6.499 8.446 -2.570 -0.758 -5.482 "H6'3" CMD 73 CMD H33 H33 H 0 1 N N N 15.077 9.290 10.574 2.670 -1.911 -4.119 H33 CMD 74 CMD H231 1H23 H 0 0 N N N 16.268 11.145 11.710 4.086 -0.565 -6.462 H231 CMD 75 CMD H232 2H23 H 0 0 N N N 16.257 9.952 12.862 4.273 -2.273 -6.000 H232 CMD 76 CMD H631 1H63 H 0 0 N N N 18.736 11.730 10.652 4.774 1.085 -5.157 H631 CMD 77 CMD H632 2H63 H 0 0 N N N 19.701 10.368 10.367 5.547 0.783 -3.583 H632 CMD 78 CMD H531 1H53 H 0 0 N N N 18.405 10.078 8.444 3.228 1.529 -3.248 H531 CMD 79 CMD H532 2H53 H 0 0 N N N 17.196 11.158 8.990 3.397 -0.167 -2.740 H532 CMD 80 # 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 CMD C1 C2 DOUB Y N 1 CMD C1 C20 SING Y N 2 CMD C1 H1 SING N N 3 CMD C2 C3 SING Y N 4 CMD C2 H2 SING N N 5 CMD C3 C4 DOUB Y N 6 CMD C3 H3 SING N N 7 CMD C4 O4 SING N N 8 CMD C4 C5 SING Y N 9 CMD O4 C21 SING N N 10 CMD C5 C6 SING N N 11 CMD C5 C20 DOUB Y N 12 CMD C6 O6 DOUB N N 13 CMD C6 C7 SING N N 14 CMD C7 C8 DOUB Y N 15 CMD C7 C18 SING Y N 16 CMD C8 O8 SING N N 17 CMD C8 C9 SING Y N 18 CMD O8 HO8 SING N N 19 CMD C9 C10 SING N N 20 CMD C9 C16 DOUB Y N 21 CMD C10 O10 SING N N 22 CMD C10 C11 SING N N 23 CMD C10 H10 SING N N 24 CMD O10 "C1'" SING N N 25 CMD C11 C12 SING N N 26 CMD C11 H111 SING N N 27 CMD C11 H112 SING N N 28 CMD C12 O12 SING N N 29 CMD C12 C13 SING N N 30 CMD C12 C15 SING N N 31 CMD O12 HO12 SING N N 32 CMD C13 O13 DOUB N N 33 CMD C13 C14 SING N N 34 CMD C14 O14 SING N N 35 CMD C14 H141 SING N N 36 CMD C14 H142 SING N N 37 CMD O14 HO14 SING N N 38 CMD C15 C16 SING N N 39 CMD C15 H151 SING N N 40 CMD C15 H152 SING N N 41 CMD C16 C17 SING Y N 42 CMD C17 O17 SING N N 43 CMD C17 C18 DOUB Y N 44 CMD O17 HO17 SING N N 45 CMD C18 C19 SING N N 46 CMD C19 O19 DOUB N N 47 CMD C19 C20 SING N N 48 CMD C21 H211 SING N N 49 CMD C21 H212 SING N N 50 CMD C21 H213 SING N N 51 CMD "C1'" "C2'" SING N N 52 CMD "C1'" "O5'" SING N N 53 CMD "C1'" "H1'" SING N N 54 CMD "C2'" "C3'" SING N N 55 CMD "C2'" "H2'1" SING N N 56 CMD "C2'" "H2'2" SING N N 57 CMD "C3'" "C4'" SING N N 58 CMD "C3'" "N3'" SING N N 59 CMD "C3'" "H3'" SING N N 60 CMD "C4'" "O4'" SING N N 61 CMD "C4'" "C5'" SING N N 62 CMD "C4'" "H4'" SING N N 63 CMD "O4'" "HO4'" SING N N 64 CMD "C5'" "O5'" SING N N 65 CMD "C5'" "C6'" SING N N 66 CMD "C5'" "H5'" SING N N 67 CMD "C6'" "H6'1" SING N N 68 CMD "C6'" "H6'2" SING N N 69 CMD "C6'" "H6'3" SING N N 70 CMD "N3'" C33 SING N N 71 CMD "N3'" C53 SING N N 72 CMD C33 C23 SING N N 73 CMD C33 C73 SING N N 74 CMD C33 H33 SING N N 75 CMD C23 O16 SING N N 76 CMD C23 H231 SING N N 77 CMD C23 H232 SING N N 78 CMD O16 C63 SING N N 79 CMD C63 C53 SING N N 80 CMD C63 H631 SING N N 81 CMD C63 H632 SING N N 82 CMD C53 H531 SING N N 83 CMD C53 H532 SING N N 84 CMD C73 N73 TRIP N N 85 # 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 CMD SMILES ACDLabs 10.04 "N#CC6N(C5C(O)C(OC(OC4c3c(O)c2C(=O)c1c(OC)cccc1C(=O)c2c(O)c3CC(O)(C(=O)CO)C4)C5)C)CCOC6" CMD SMILES_CANONICAL CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@@H]([C@H](O)[C@H](C)O5)N6CCOC[C@@H]6C#N)c4c(O)c3C(=O)c12)C(=O)CO" CMD SMILES CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH]([CH](O)[CH](C)O5)N6CCOC[CH]6C#N)c4c(O)c3C(=O)c12)C(=O)CO" CMD 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(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)[N@]6CCOC[C@@H]6C#N)O" CMD SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N6CCOCC6C#N)O" CMD InChI InChI 1.03 ;InChI=1S/C32H34N2O12/c1-14-27(37)18(34-6-7-44-13-15(34)11-33)8-22(45-14)46-20-10-32(42,21(36)12-35)9-17-24(20)31(41)26-25(29(17)39)28(38)16-4-3-5-19(43-2)23(16)30(26)40/h3-5,14-15,18,20,22,27,35,37,39,41-42H,6-10,12-13H2,1-2H3/t14-,15-,18-,20-,22-,27+,32-/m0/s1 ; CMD InChIKey InChI 1.03 YIMDLWDNDGKDTJ-USRAFFTGSA-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 CMD "SYSTEMATIC NAME" ACDLabs 10.04 "(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-[(3S)-3-cyanomorpholin-4-yl]-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" CMD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3S,4S)-4-[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyethanoyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]morpholine-3-carbonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CMD "Create component" 1999-07-08 RCSB CMD "Modify descriptor" 2011-06-04 RCSB #