data_DM5
# 
_chem_comp.id                                    DM5 
_chem_comp.name                                  IDARUBICIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C26 H27 N O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         4-DEMETHOXY-DAUNORUBICIN 
_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                        497.494 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM5 
_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        1D67 
_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 
DM5 C1     C1   C 0 1 Y N N -12.748 18.560 4.966  -0.481 -0.601 -6.318 C1     DM5 1  
DM5 C2     C2   C 0 1 Y N N -11.592 19.243 4.982  -1.668 -0.492 -7.021 C2     DM5 2  
DM5 C3     C3   C 0 1 Y N N -10.447 18.619 4.913  -2.804 0.000  -6.406 C3     DM5 3  
DM5 C4     C4   C 0 1 Y N N -10.278 17.295 4.828  -2.771 0.390  -5.079 C4     DM5 4  
DM5 C5     C5   C 0 1 Y N N -11.456 16.522 4.865  -1.586 0.286  -4.357 C5     DM5 5  
DM5 C6     C6   C 0 1 N N N -11.392 14.986 4.813  -1.531 0.695  -2.936 C6     DM5 6  
DM5 O6     O6   O 0 1 N N N -10.354 14.385 4.723  -2.431 1.353  -2.450 O6     DM5 7  
DM5 C7     C7   C 0 1 Y N N -12.717 14.290 4.834  -0.372 0.296  -2.117 C7     DM5 8  
DM5 C8     C8   C 0 1 Y N N -12.674 12.891 4.781  -0.404 0.408  -0.730 C8     DM5 9  
DM5 O8     O8   O 0 1 N N N -11.516 12.167 4.781  -1.514 0.893  -0.120 O8     DM5 10 
DM5 C9     C9   C 0 1 Y N N -13.889 12.147 4.770  0.702  0.024  0.039  C9     DM5 11 
DM5 C10    C10  C 0 1 N N S -13.827 10.650 4.886  0.592  0.182  1.534  C10    DM5 12 
DM5 O10    O10  O 0 1 N N N -13.215 10.419 6.121  -0.703 -0.244 1.959  O10    DM5 13 
DM5 C11    C11  C 0 1 N N N -15.183 10.033 4.649  1.655  -0.653 2.243  C11    DM5 14 
DM5 C12    C12  C 0 1 N N S -16.316 10.721 5.467  3.018  -0.330 1.619  C12    DM5 15 
DM5 O12    O12  O 0 1 N N N -16.133 10.740 6.876  4.058  -0.924 2.398  O12    DM5 16 
DM5 C13    C13  C 0 1 N N N -17.613 10.044 5.040  3.211  1.163  1.567  C13    DM5 17 
DM5 O13    O13  O 0 1 N N N -18.301 10.292 3.995  2.941  1.772  0.560  O13    DM5 18 
DM5 C14    C14  C 0 1 N N N -18.036 8.857  5.747  3.743  1.896  2.772  C14    DM5 19 
DM5 C15    C15  C 0 1 N N N -16.412 12.122 4.897  3.045  -0.902 0.203  C15    DM5 20 
DM5 C16    C16  C 0 1 Y N N -15.099 12.829 4.818  1.827  -0.466 -0.570 C16    DM5 21 
DM5 C17    C17  C 0 1 Y N N -15.082 14.273 4.886  1.877  -0.582 -1.967 C17    DM5 22 
DM5 O17    O17  O 0 1 N N N -16.297 14.980 4.781  2.995  -1.066 -2.563 O17    DM5 23 
DM5 C18    C18  C 0 1 Y N N -13.881 14.966 4.876  0.787  -0.205 -2.745 C18    DM5 24 
DM5 C19    C19  C 0 1 N N N -13.917 16.392 4.923  0.829  -0.324 -4.214 C19    DM5 25 
DM5 O19    O19  O 0 1 N N N -14.991 17.075 4.934  1.885  -0.510 -4.787 O19    DM5 26 
DM5 C20    C20  C 0 1 Y N N -12.708 17.148 4.918  -0.430 -0.214 -4.983 C20    DM5 27 
DM5 "C1'"  C1*  C 0 1 N N R -12.336 9.280  6.459  -1.224 0.789  2.797  "C1'"  DM5 28 
DM5 "C2'"  C2*  C 0 1 N N N -11.149 9.678  7.377  -2.724 0.565  3.005  "C2'"  DM5 29 
DM5 "C3'"  C3*  C 0 1 N N S -11.674 9.810  8.844  -2.939 -0.811 3.644  "C3'"  DM5 30 
DM5 "N3'"  N3*  N 0 1 N N N -10.659 10.591 9.583  -4.358 -0.977 3.989  "N3'"  DM5 31 
DM5 "C4'"  C4*  C 0 1 N N S -12.533 8.626  9.282  -2.084 -0.900 4.913  "C4'"  DM5 32 
DM5 "O4'"  O4*  O 0 1 N N N -11.476 7.547  9.134  -2.570 0.028  5.883  "O4'"  DM5 33 
DM5 "C5'"  C5*  C 0 1 N N S -13.627 8.511  8.348  -0.633 -0.567 4.560  "C5'"  DM5 34 
DM5 "O5'"  O5*  O 0 1 N N N -13.193 8.268  7.018  -0.553 0.764  4.055  "O5'"  DM5 35 
DM5 "C6'"  C6*  C 0 1 N N N -14.462 7.490  8.876  0.235  -0.688 5.813  "C6'"  DM5 36 
DM5 H1     H1   H 0 1 N N N -13.689 19.133 4.991  0.403  -0.986 -6.804 H1     DM5 37 
DM5 H2     H2   H 0 1 N N N -11.582 20.343 5.053  -1.707 -0.793 -8.058 H2     DM5 38 
DM5 H3     H3   H 0 1 N N N -9.550  19.261 4.927  -3.724 0.082  -6.966 H3     DM5 39 
DM5 H4     H4   H 0 1 N N N -9.260  16.878 4.735  -3.662 0.775  -4.605 H4     DM5 40 
DM5 HO8    HO8  H 0 1 N N N -11.486 11.218 4.745  -2.120 0.148  -0.010 HO8    DM5 41 
DM5 H10    H10  H 0 1 N N N -13.220 10.140 4.101  0.728  1.232  1.795  H10    DM5 42 
DM5 H111   1H11 H 0 0 N N N -15.429 10.019 3.561  1.670  -0.406 3.305  H111   DM5 43 
DM5 H112   2H11 H 0 0 N N N -15.160 8.935  4.845  1.435  -1.713 2.115  H112   DM5 44 
DM5 HO12   2HO1 H 0 0 N N N -16.824 11.159 7.374  4.894  -0.695 1.970  HO12   DM5 45 
DM5 H141   1H14 H 0 0 N N N -18.984 8.361  5.434  3.814  2.960  2.547  H141   DM5 46 
DM5 H142   2H14 H 0 0 N N N -17.210 8.107  5.722  3.068  1.747  3.615  H142   DM5 47 
DM5 H143   3H14 H 0 0 N N N -18.087 9.083  6.837  4.731  1.511  3.025  H143   DM5 48 
DM5 H151   1H15 H 0 0 N N N -16.911 12.107 3.900  3.941  -0.551 -0.308 H151   DM5 49 
DM5 H152   2H15 H 0 0 N N N -17.152 12.729 5.468  3.066  -1.991 0.257  H152   DM5 50 
DM5 HO17   7HO1 H 0 0 N N N -16.285 15.928 4.825  2.885  -2.024 -2.626 HO17   DM5 51 
DM5 "H1'"  H1*  H 0 1 N N N -11.821 8.888  5.550  -1.065 1.756  2.320  "H1'"  DM5 52 
DM5 "H2'1" 1H2* H 0 0 N N N -10.289 8.973  7.293  -3.120 1.339  3.662  "H2'1" DM5 53 
DM5 "H2'2" 2H2* H 0 0 N N N -10.627 10.598 7.025  -3.235 0.605  2.043  "H2'2" DM5 54 
DM5 "H3'"  H3*  H 0 1 N N N -12.547 10.440 9.132  -2.639 -1.590 2.943  "H3'"  DM5 55 
DM5 "HN'1" 1HN* H 0 0 N N N -11.001 10.677 10.539 -4.877 -0.897 3.127  "HN'1" DM5 56 
DM5 "HN'2" 2HN* H 0 0 N N N -10.444 11.488 9.148  -4.469 -1.928 4.307  "HN'2" DM5 57 
DM5 "H4'"  H4*  H 0 1 N N N -13.020 8.640  10.284 -2.137 -1.911 5.317  "H4'"  DM5 58 
DM5 "HO4'" *HO4 H 0 0 N N N -12.010 6.810  9.406  -2.005 -0.060 6.663  "HO4'" DM5 59 
DM5 "H5'"  H5*  H 0 1 N N N -14.189 9.468  8.250  -0.275 -1.264 3.802  "H5'"  DM5 60 
DM5 "H6'1" 1H6* H 0 0 N N N -15.307 7.401  8.154  1.270  -0.453 5.563  "H6'1" DM5 61 
DM5 "H6'2" 2H6* H 0 0 N N N -13.931 6.528  9.068  -0.121 0.008  6.572  "H6'2" DM5 62 
DM5 "H6'3" 3H6* H 0 0 N N N -14.785 7.671  9.927  0.177  -1.706 6.199  "H6'3" DM5 63 
# 
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 
DM5 C1    C2     DOUB Y N 1  
DM5 C1    C20    SING Y N 2  
DM5 C1    H1     SING N N 3  
DM5 C2    C3     SING Y N 4  
DM5 C2    H2     SING N N 5  
DM5 C3    C4     DOUB Y N 6  
DM5 C3    H3     SING N N 7  
DM5 C4    C5     SING Y N 8  
DM5 C4    H4     SING N N 9  
DM5 C5    C6     SING N N 10 
DM5 C5    C20    DOUB Y N 11 
DM5 C6    O6     DOUB N N 12 
DM5 C6    C7     SING N N 13 
DM5 C7    C8     DOUB Y N 14 
DM5 C7    C18    SING Y N 15 
DM5 C8    O8     SING N N 16 
DM5 C8    C9     SING Y N 17 
DM5 O8    HO8    SING N N 18 
DM5 C9    C10    SING N N 19 
DM5 C9    C16    DOUB Y N 20 
DM5 C10   O10    SING N N 21 
DM5 C10   C11    SING N N 22 
DM5 C10   H10    SING N N 23 
DM5 O10   "C1'"  SING N N 24 
DM5 C11   C12    SING N N 25 
DM5 C11   H111   SING N N 26 
DM5 C11   H112   SING N N 27 
DM5 C12   O12    SING N N 28 
DM5 C12   C13    SING N N 29 
DM5 C12   C15    SING N N 30 
DM5 O12   HO12   SING N N 31 
DM5 C13   O13    DOUB N N 32 
DM5 C13   C14    SING N N 33 
DM5 C14   H141   SING N N 34 
DM5 C14   H142   SING N N 35 
DM5 C14   H143   SING N N 36 
DM5 C15   C16    SING N N 37 
DM5 C15   H151   SING N N 38 
DM5 C15   H152   SING N N 39 
DM5 C16   C17    SING Y N 40 
DM5 C17   O17    SING N N 41 
DM5 C17   C18    DOUB Y N 42 
DM5 O17   HO17   SING N N 43 
DM5 C18   C19    SING N N 44 
DM5 C19   O19    DOUB N N 45 
DM5 C19   C20    SING N N 46 
DM5 "C1'" "C2'"  SING N N 47 
DM5 "C1'" "O5'"  SING N N 48 
DM5 "C1'" "H1'"  SING N N 49 
DM5 "C2'" "C3'"  SING N N 50 
DM5 "C2'" "H2'1" SING N N 51 
DM5 "C2'" "H2'2" SING N N 52 
DM5 "C3'" "N3'"  SING N N 53 
DM5 "C3'" "C4'"  SING N N 54 
DM5 "C3'" "H3'"  SING N N 55 
DM5 "N3'" "HN'1" SING N N 56 
DM5 "N3'" "HN'2" SING N N 57 
DM5 "C4'" "O4'"  SING N N 58 
DM5 "C4'" "C5'"  SING N N 59 
DM5 "C4'" "H4'"  SING N N 60 
DM5 "O4'" "HO4'" SING N N 61 
DM5 "C5'" "O5'"  SING N N 62 
DM5 "C5'" "C6'"  SING N N 63 
DM5 "C5'" "H5'"  SING N N 64 
DM5 "C6'" "H6'1" SING N N 65 
DM5 "C6'" "H6'2" SING N N 66 
DM5 "C6'" "H6'3" SING N N 67 
# 
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 
DM5 SMILES           ACDLabs              10.04 O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)CC(O)(C(=O)C)CC5OC4OC(C(O)C(N)C4)C                                                                                                                                         
DM5 InChI            InChI                1.02b InChI=1/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1 
DM5 InChIKey         InChI                1.02b XDXDZDZNSLXDNA-TZNDIEGXBV                                                                                                                                                                                     
DM5 SMILES_CANONICAL CACTVS               3.341 C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(Cc3c(O)c4C(=O)c5ccccc5C(=O)c4c(O)c23)C(C)=O                                                                                                                 
DM5 SMILES           CACTVS               3.341 C[CH]1O[CH](C[CH](N)[CH]1O)O[CH]2C[C](O)(Cc3c(O)c4C(=O)c5ccccc5C(=O)c4c(O)c23)C(C)=O                                                                                                                          
DM5 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)c5ccccc5C4=O)O)(C(=O)C)O)N)O                                                                                                                  
DM5 SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5ccccc5C4=O)O)(C(=O)C)O)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 
DM5 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" 
DM5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione    
# 
