data_DM6
# 
_chem_comp.id                                    DM6 
_chem_comp.name                                  "4'-EPIDOXORUBICIN" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H30 N O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "4'-EPIADRIAMYCIN" 
_chem_comp.pdbx_formal_charge                    1 
_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                        544.527 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM6 
_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        1D54 
_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 
DM6 C1     C1   C 0 1 Y N N -12.455 18.476 5.182  6.084  -0.803 -0.683 C1     DM6 1  
DM6 C2     C2   C 0 1 Y N N -11.236 19.166 5.198  7.044  0.037  -0.142 C2     DM6 2  
DM6 C3     C3   C 0 1 Y N N -10.062 18.558 5.108  6.680  1.219  0.469  C3     DM6 3  
DM6 C4     C4   C 0 1 Y N N -9.992  17.168 4.949  5.340  1.586  0.550  C4     DM6 4  
DM6 C5     C5   C 0 1 N N N -11.208 14.923 4.817  2.933  1.117  0.084  C5     DM6 5  
DM6 C6     C6   C 0 1 Y N N -12.508 12.875 4.732  0.576  0.305  0.120  C6     DM6 6  
DM6 C7     C7   C 0 1 N N S -13.668 10.642 4.811  -1.812 -0.375 0.235  C7     DM6 7  
DM6 C8     C8   C 0 1 N N N -14.993 10.012 4.483  -2.780 -1.299 -0.500 C8     DM6 8  
DM6 C9     C9   C 0 1 N N S -16.170 10.603 5.304  -2.305 -2.744 -0.314 C9     DM6 9  
DM6 C10    C10  C 0 1 N N N -16.299 12.096 4.928  -1.013 -2.930 -1.108 C10    DM6 10 
DM6 C11    C11  C 0 1 Y N N -14.932 14.240 4.907  1.319  -2.073 -1.110 C11    DM6 11 
DM6 C12    C12  C 0 1 N N N -13.713 16.395 5.050  3.703  -1.342 -1.185 C12    DM6 12 
DM6 C13    C13  C 0 1 N N N -17.501 9.899  4.907  -2.046 -3.011 1.147  C13    DM6 13 
DM6 C14    C14  C 0 1 N N N -18.185 9.336  6.161  -3.178 -3.431 2.048  C14    DM6 14 
DM6 C15    C15  C 0 1 Y N N -12.402 17.089 5.034  4.740  -0.456 -0.613 C15    DM6 15 
DM6 C16    C16  C 0 1 Y N N -11.214 16.414 4.922  4.360  0.747  0.014  C16    DM6 16 
DM6 C17    C17  C 0 1 Y N N -12.505 14.257 4.848  1.911  0.095  -0.211 C17    DM6 17 
DM6 C18    C18  C 0 1 Y N N -13.705 14.935 4.949  2.289  -1.113 -0.834 C18    DM6 18 
DM6 C19    C19  C 0 1 Y N N -14.940 12.811 4.822  -0.022 -1.846 -0.771 C19    DM6 19 
DM6 C20    C20  C 0 1 Y N N -13.758 12.141 4.764  -0.388 -0.673 -0.161 C20    DM6 20 
DM6 C21    C21  C 0 1 N N N -7.591  17.145 5.214  6.195  3.368  1.595  C21    DM6 21 
DM6 O4     O4   O 0 1 N N N -8.857  16.470 4.901  4.986  2.749  1.152  O4     DM6 22 
DM6 O5     O5   O 0 1 N N N -10.157 14.262 4.705  2.604  2.248  0.385  O5     DM6 23 
DM6 O6     O6   O 0 1 N N N -11.387 12.127 4.727  0.204  1.464  0.719  O6     DM6 24 
DM6 O7     O7   O 0 1 N N N -13.189 10.250 6.124  -2.116 0.982  -0.090 O7     DM6 25 
DM6 O9     O9   O 0 1 N N N -16.055 10.533 6.727  -3.302 -3.646 -0.798 O9     DM6 26 
DM6 O11    O11  O 0 1 N N N -16.128 14.873 4.880  1.674  -3.235 -1.712 O11    DM6 27 
DM6 O12    O12  O 0 1 N N N -14.769 17.036 5.023  4.012  -2.248 -1.934 O12    DM6 28 
DM6 O13    O13  O 0 1 N N N -17.924 10.311 3.822  -0.931 -2.887 1.595  O13    DM6 29 
DM6 O14    O14  O 0 1 N N N -19.009 8.272  5.685  -2.684 -3.621 3.376  O14    DM6 30 
DM6 "C1'"  C1*  C 0 1 N N R -12.292 9.154  6.071  -2.933 1.488  0.968  "C1'"  DM6 31 
DM6 "C2'"  C2*  C 0 1 N N N -11.513 9.224  7.341  -2.992 3.015  0.879  "C2'"  DM6 32 
DM6 "C3'"  C3*  C 0 1 N N S -12.410 8.930  8.564  -3.566 3.414  -0.485 "C3'"  DM6 33 
DM6 "C4'"  C4*  C 0 1 N N R -13.158 7.641  8.363  -4.906 2.696  -0.682 "C4'"  DM6 34 
DM6 "C5'"  C5*  C 0 1 N N S -13.912 7.661  7.061  -4.702 1.193  -0.476 "C5'"  DM6 35 
DM6 "C6'"  C6*  C 0 1 N N N -14.663 6.349  6.738  -6.027 0.464  -0.702 "C6'"  DM6 36 
DM6 "O4'"  O4*  O 0 1 N N N -13.929 7.310  9.490  -5.387 2.937  -2.006 "O4'"  DM6 37 
DM6 "O5'"  O5*  O 0 1 N N N -13.010 7.907  5.960  -4.247 0.947  0.853  "O5'"  DM6 38 
DM6 "N3'"  N3*  N 1 1 N N N -11.502 8.790  9.734  -3.771 4.868  -0.527 "N3'"  DM6 39 
DM6 H1     H1   H 0 1 N N N -13.418 19.003 5.282  6.379  -1.726 -1.160 H1     DM6 40 
DM6 H2     H2   H 0 1 N N N -11.197 20.264 5.287  8.088  -0.237 -0.198 H2     DM6 41 
DM6 H3     H3   H 0 1 N N N -9.163  19.194 5.164  7.439  1.864  0.886  H3     DM6 42 
DM6 H7     H7   H 0 1 N N N -12.948 10.278 4.040  -1.924 -0.521 1.310  H7     DM6 43 
DM6 H81    1H8  H 0 1 N N N -15.201 10.073 3.389  -2.791 -1.049 -1.561 H81    DM6 44 
DM6 H82    2H8  H 0 1 N N N -14.945 8.904  4.598  -3.782 -1.185 -0.086 H82    DM6 45 
DM6 H101   1H10 H 0 0 N N N -16.887 12.220 3.989  -1.238 -2.892 -2.173 H101   DM6 46 
DM6 H102   2H10 H 0 0 N N N -16.973 12.628 5.638  -0.580 -3.901 -0.867 H102   DM6 47 
DM6 H141   1H14 H 0 0 N N N -17.475 9.032  6.965  -3.945 -2.656 2.054  H141   DM6 48 
DM6 H142   2H14 H 0 0 N N N -18.734 10.100 6.757  -3.607 -4.364 1.683  H142   DM6 49 
DM6 H211   1H21 H 0 0 N N N -6.641  16.561 5.173  5.960  4.312  2.088  H211   DM6 50 
DM6 H212   2H21 H 0 0 N N N -7.489  18.040 4.556  6.705  2.709  2.297  H212   DM6 51 
DM6 H213   3H21 H 0 0 N N N -7.677  17.621 6.218  6.842  3.557  0.738  H213   DM6 52 
DM6 HO6    HO6  H 0 1 N N N -11.389 11.180 4.647  0.198  1.296  1.672  HO6    DM6 53 
DM6 HO9    HO9  H 0 1 N N N -16.775 10.894 7.229  -2.952 -4.540 -0.678 HO9    DM6 54 
DM6 HO11   HO11 H 0 0 N N N -16.954 14.405 4.851  1.892  -3.860 -1.006 HO11   DM6 55 
DM6 HO14   HO14 H 0 0 N N N -19.432 7.923  6.460  -3.438 -3.889 3.919  HO14   DM6 56 
DM6 "H1'"  H1*  H 0 1 N N N -11.624 9.202  5.179  -2.504 1.197  1.927  "H1'"  DM6 57 
DM6 "H2'1" 1H2* H 0 0 N N N -10.623 8.551  7.313  -3.633 3.401  1.672  "H2'1" DM6 58 
DM6 "H2'2" 2H2* H 0 0 N N N -10.985 10.200 7.445  -1.988 3.425  0.987  "H2'2" DM6 59 
DM6 "H3'"  H3*  H 0 1 N N N -13.154 9.746  8.712  -2.874 3.119  -1.273 "H3'"  DM6 60 
DM6 "H4'"  H4*  H 0 1 N N N -12.428 6.802  8.269  -5.630 3.068  0.043  "H4'"  DM6 61 
DM6 "H5'"  H5*  H 0 1 N N N -14.664 8.474  7.185  -3.961 0.827  -1.186 "H5'"  DM6 62 
DM6 "H6'1" 1H6* H 0 0 N N N -15.221 6.363  5.773  -6.374 0.647  -1.719 "H6'1" DM6 63 
DM6 "H6'2" 2H6* H 0 0 N N N -13.962 5.482  6.768  -5.883 -0.607 -0.555 "H6'2" DM6 64 
DM6 "H6'3" 3H6* H 0 0 N N N -15.343 6.073  7.577  -6.770 0.831  0.006  "H6'3" DM6 65 
DM6 "HO'4" 4HO* H 0 0 N N N -14.401 6.495  9.363  -6.229 2.468  -2.087 "HO'4" DM6 66 
DM6 "HN'1" 1HN* H 0 0 N N N -12.094 8.595  10.541 -2.889 5.336  -0.384 "HN'1" DM6 67 
DM6 "HN'2" 2HN* H 0 0 N N N -10.769 8.093  9.594  -4.149 5.128  -1.425 "HN'2" DM6 68 
DM6 "HN'3" 3HN* H 0 0 N N N -10.889 9.594  9.867  -4.417 5.137  0.200  "HN'3" DM6 69 
# 
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 
DM6 C1    C2     DOUB Y N 1  
DM6 C1    C15    SING Y N 2  
DM6 C1    H1     SING N N 3  
DM6 C2    C3     SING Y N 4  
DM6 C2    H2     SING N N 5  
DM6 C3    C4     DOUB Y N 6  
DM6 C3    H3     SING N N 7  
DM6 C4    C16    SING Y N 8  
DM6 C4    O4     SING N N 9  
DM6 C5    C16    SING N N 10 
DM6 C5    C17    SING N N 11 
DM6 C5    O5     DOUB N N 12 
DM6 C6    C17    DOUB Y N 13 
DM6 C6    C20    SING Y N 14 
DM6 C6    O6     SING N N 15 
DM6 C7    C8     SING N N 16 
DM6 C7    C20    SING N N 17 
DM6 C7    O7     SING N N 18 
DM6 C7    H7     SING N N 19 
DM6 C8    C9     SING N N 20 
DM6 C8    H81    SING N N 21 
DM6 C8    H82    SING N N 22 
DM6 C9    C10    SING N N 23 
DM6 C9    C13    SING N N 24 
DM6 C9    O9     SING N N 25 
DM6 C10   C19    SING N N 26 
DM6 C10   H101   SING N N 27 
DM6 C10   H102   SING N N 28 
DM6 C11   C18    DOUB Y N 29 
DM6 C11   C19    SING Y N 30 
DM6 C11   O11    SING N N 31 
DM6 C12   C15    SING N N 32 
DM6 C12   C18    SING N N 33 
DM6 C12   O12    DOUB N N 34 
DM6 C13   C14    SING N N 35 
DM6 C13   O13    DOUB N N 36 
DM6 C14   O14    SING N N 37 
DM6 C14   H141   SING N N 38 
DM6 C14   H142   SING N N 39 
DM6 C15   C16    DOUB Y N 40 
DM6 C17   C18    SING Y N 41 
DM6 C19   C20    DOUB Y N 42 
DM6 C21   O4     SING N N 43 
DM6 C21   H211   SING N N 44 
DM6 C21   H212   SING N N 45 
DM6 C21   H213   SING N N 46 
DM6 O6    HO6    SING N N 47 
DM6 O7    "C1'"  SING N N 48 
DM6 O9    HO9    SING N N 49 
DM6 O11   HO11   SING N N 50 
DM6 O14   HO14   SING N N 51 
DM6 "C1'" "C2'"  SING N N 52 
DM6 "C1'" "O5'"  SING N N 53 
DM6 "C1'" "H1'"  SING N N 54 
DM6 "C2'" "C3'"  SING N N 55 
DM6 "C2'" "H2'1" SING N N 56 
DM6 "C2'" "H2'2" SING N N 57 
DM6 "C3'" "C4'"  SING N N 58 
DM6 "C3'" "N3'"  SING N N 59 
DM6 "C3'" "H3'"  SING N N 60 
DM6 "C4'" "C5'"  SING N N 61 
DM6 "C4'" "O4'"  SING N N 62 
DM6 "C4'" "H4'"  SING N N 63 
DM6 "C5'" "C6'"  SING N N 64 
DM6 "C5'" "O5'"  SING N N 65 
DM6 "C5'" "H5'"  SING N N 66 
DM6 "C6'" "H6'1" SING N N 67 
DM6 "C6'" "H6'2" SING N N 68 
DM6 "C6'" "H6'3" SING N N 69 
DM6 "O4'" "HO'4" SING N N 70 
DM6 "N3'" "HN'1" SING N N 71 
DM6 "N3'" "HN'2" SING N N 72 
DM6 "N3'" "HN'3" SING N N 73 
# 
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 
DM6 SMILES           ACDLabs              10.04 O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)CO)CC5OC4OC(C(O)C(C4)[NH3+])C 
DM6 InChI            InChI                1.02b 
InChI=1/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/p+1/t10-,13-,15-,17-,22-,27-/m0/s1/fC27H30NO11/h28H/q+1 
DM6 InChIKey         InChI                1.02b AOJJSUZBOXZQNB-HCHUQNLMDW 
DM6 SMILES_CANONICAL CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H]([NH3+])[C@@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO 
DM6 SMILES           CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH]([NH3+])[CH](O)[CH](C)O5)c4c(O)c3C(=O)c12)C(=O)CO 
DM6 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)[NH3+])O 
DM6 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)[NH3+])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 
DM6 "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-ammonio-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside" 
DM6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [(2S,3R,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]azanium  
# 
