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                    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                        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 InChI            InChI                1.02b 
InChI=1/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                1.02b IURHBLXSEHXXFF-XGGCRALDBG 
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 
# 
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 
# 
