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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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                1.02b YIMDLWDNDGKDTJ-USRAFFTGBS 
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 
# 
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 
# 
