data_DM1
# 
_chem_comp.id                                    DM1 
_chem_comp.name                                  DAUNOMYCIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H29 N O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         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                        527.520 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM1 
_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        1D11 
_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 
DM1 C1     C1   C 0 1 Y N N 15.076 18.210 5.093  -0.723 -0.349 6.044  C1     DM1 1  
DM1 C2     C2   C 0 1 Y N N 16.284 18.936 5.143  0.243  0.085  6.939  C2     DM1 2  
DM1 C3     C3   C 0 1 Y N N 17.527 18.293 5.081  1.488  0.476  6.492  C3     DM1 3  
DM1 C4     C4   C 0 1 Y N N 17.520 16.910 5.002  1.792  0.441  5.134  C4     DM1 4  
DM1 O4     O4   O 0 1 N N N 18.754 16.294 4.969  3.017  0.827  4.699  O4     DM1 5  
DM1 C5     C5   C 0 1 Y N N 16.334 16.176 4.980  0.826  0.012  4.221  C5     DM1 6  
DM1 C6     C6   C 0 1 N N N 16.306 14.768 4.911  1.126  -0.038 2.777  C6     DM1 7  
DM1 O6     O6   O 0 1 N N N 17.462 14.041 4.823  2.273  0.058  2.382  O6     DM1 8  
DM1 C7     C7   C 0 1 Y N N 15.089 14.049 4.912  0.018  -0.201 1.818  C7     DM1 9  
DM1 C8     C8   C 0 1 Y N N 15.065 12.635 4.850  0.208  0.035  0.459  C8     DM1 10 
DM1 O8     O8   O 0 1 N N N 16.272 11.915 4.864  1.428  0.419  0.007  O8     DM1 11 
DM1 C9     C9   C 0 1 Y N N 13.847 11.929 4.810  -0.851 -0.118 -0.444 C9     DM1 12 
DM1 C10    C10  C 0 1 N N S 13.931 10.456 4.819  -0.569 0.164  -1.897 C10    DM1 13 
DM1 O10    O10  O 0 1 N N N 14.546 10.208 6.171  0.699  -0.393 -2.246 O10    DM1 14 
DM1 C11    C11  C 0 1 N N N 12.603 9.711  4.699  -1.649 -0.447 -2.785 C11    DM1 15 
DM1 C12    C12  C 0 1 N N S 11.442 10.539 5.370  -3.018 -0.005 -2.254 C12    DM1 16 
DM1 O12    O12  O 0 1 N N N 11.531 10.603 6.805  -4.038 -0.375 -3.184 O12    DM1 17 
DM1 C13    C13  C 0 1 N N N 10.153 9.725  5.149  -3.029 1.487  -2.055 C13    DM1 18 
DM1 O13    O13  O 0 1 N N N 9.415  10.008 4.095  -2.773 1.954  -0.971 O13    DM1 19 
DM1 C14    C14  C 0 1 N N N 9.798  8.587  6.083  -3.358 2.399  -3.209 C14    DM1 20 
DM1 C15    C15  C 0 1 N N N 11.346 11.979 4.813  -3.262 -0.705 -0.918 C15    DM1 21 
DM1 C16    C16  C 0 1 Y N N 12.679 12.633 4.852  -2.087 -0.511 0.004  C16    DM1 22 
DM1 C17    C17  C 0 1 Y N N 12.674 14.045 4.878  -2.295 -0.754 1.369  C17    DM1 23 
DM1 O17    O17  O 0 1 N N N 11.428 14.623 4.847  -3.519 -1.140 1.806  O17    DM1 24 
DM1 C18    C18  C 0 1 Y N N 13.866 14.761 4.931  -1.252 -0.601 2.280  C18    DM1 25 
DM1 C19    C19  C 0 1 N N N 13.865 16.186 4.984  -1.461 -0.851 3.718  C19    DM1 26 
DM1 O19    O19  O 0 1 N N N 12.738 16.887 5.004  -2.460 -1.427 4.104  O19    DM1 27 
DM1 C20    C20  C 0 1 Y N N 15.112 16.834 4.999  -0.440 -0.391 4.685  C20    DM1 28 
DM1 C21    C21  C 0 1 N N N 19.976 17.161 5.150  3.763  1.211  5.855  C21    DM1 29 
DM1 "C1'"  C1*  C 0 1 N N R 15.484 9.139  6.380  1.456  0.653  -2.858 "C1'"  DM1 30 
DM1 "C2'"  C2*  C 0 1 N N N 16.539 9.605  7.374  2.919  0.220  -2.976 "C2'"  DM1 31 
DM1 "C3'"  C3*  C 0 1 N N S 15.948 9.604  8.804  2.995  -1.062 -3.812 "C3'"  DM1 32 
DM1 "N3'"  N3*  N 0 1 N N N 16.975 9.929  9.802  4.402  -1.404 -4.061 "N3'"  DM1 33 
DM1 "C4'"  C4*  C 0 1 N N S 15.066 8.368  9.128  2.276  -0.822 -5.144 "C4'"  DM1 34 
DM1 "O4'"  O4*  O 0 1 N N N 16.035 7.236  9.128  2.994  0.148  -5.907 "O4'"  DM1 35 
DM1 "C5'"  C5*  C 0 1 N N S 14.045 8.040  7.988  0.861  -0.311 -4.862 "C5'"  DM1 36 
DM1 "O5'"  O5*  O 0 1 N N N 14.723 7.953  6.669  0.927  0.923  -4.155 "O5'"  DM1 37 
DM1 "C6'"  C6*  C 0 1 N N N 13.253 6.745  8.148  0.124  -0.100 -6.186 "C6'"  DM1 38 
DM1 H1     H1   H 0 1 N N N 14.098 18.720 5.127  -1.694 -0.654 6.405  H1     DM1 39 
DM1 H2     H2   H 0 1 N N N 16.255 20.035 5.232  0.019  0.116  7.995  H2     DM1 40 
DM1 H3     H3   H 0 1 N N N 18.476 18.854 5.093  2.231  0.811  7.200  H3     DM1 41 
DM1 HO8    HO8  H 0 1 N N N 16.255 10.966 4.822  1.428  1.386  -0.008 HO8    DM1 42 
DM1 H10    H10  H 0 1 N N N 14.494 10.079 3.933  -0.542 1.242  -2.054 H10    DM1 43 
DM1 H111   1H11 H 0 0 N N N 12.368 9.450  3.640  -1.577 -1.534 -2.755 H111   DM1 44 
DM1 H112   2H11 H 0 0 N N N 12.668 8.678  5.113  -1.523 -0.098 -3.810 H112   DM1 45 
DM1 HO12   2HO1 H 0 0 N N N 10.831 11.102 7.209  -4.880 -0.095 -2.801 HO12   DM1 46 
DM1 H141   1H14 H 0 0 N N N 8.865  7.997  5.923  -3.316 3.436  -2.876 H141   DM1 47 
DM1 H142   2H14 H 0 0 N N N 10.658 7.878  6.115  -2.636 2.245  -4.011 H142   DM1 48 
DM1 H143   3H14 H 0 0 N N N 9.790  8.979  7.126  -4.360 2.175  -3.574 H143   DM1 49 
DM1 H151   1H15 H 0 0 N N N 10.900 12.001 3.791  -3.410 -1.770 -1.093 H151   DM1 50 
DM1 H152   2H15 H 0 0 N N N 10.571 12.580 5.343  -4.156 -0.289 -0.454 H152   DM1 51 
DM1 HO17   7HO1 H 0 0 N N N 11.424 15.572 4.864  -4.008 -0.333 2.017  HO17   DM1 52 
DM1 H211   1H21 H 0 0 N N N 20.973 16.663 5.123  4.761  1.531  5.554  H211   DM1 53 
DM1 H212   2H21 H 0 0 N N N 19.956 17.984 4.398  3.255  2.033  6.360  H212   DM1 54 
DM1 H213   3H21 H 0 0 N N N 19.879 17.738 6.098  3.843  0.362  6.534  H213   DM1 55 
DM1 "H1'"  H1*  H 0 1 N N N 16.096 8.856  5.492  1.392  1.552  -2.246 "H1'"  DM1 56 
DM1 "H2'1" 1H2* H 0 0 N N N 17.474 9.001  7.306  3.494  1.008  -3.463 "H2'1" DM1 57 
DM1 "H2'2" 2H2* H 0 0 N N N 16.966 10.597 7.097  3.325  0.033  -1.982 "H2'2" DM1 58 
DM1 "H3'"  H3*  H 0 1 N N N 15.205 10.434 8.855  2.510  -1.877 -3.275 "H3'"  DM1 59 
DM1 "HN'1" 1HN* H 0 0 N N N 16.585 9.928  10.744 4.832  -1.539 -3.159 "HN'1" DM1 60 
DM1 "HN'2" 2HN* H 0 0 N N N 17.439 10.811 9.588  4.404  -2.303 -4.521 "HN'2" DM1 61 
DM1 "H4'"  H4*  H 0 1 N N N 14.496 8.542  10.070 2.222  -1.757 -5.702 "H4'"  DM1 62 
DM1 "HO4'" *HO4 H 0 0 N N N 15.495 6.479  9.326  2.509  0.268  -6.735 "HO4'" DM1 63 
DM1 "H5'"  H5*  H 0 1 N N N 13.326 8.889  8.054  0.324  -1.045 -4.261 "H5'"  DM1 64 
DM1 "H6'1" 1H6* H 0 0 N N N 12.525 6.511  7.335  -0.883 0.263  -5.986 "H6'1" DM1 65 
DM1 "H6'2" 2H6* H 0 0 N N N 13.953 5.888  8.285  0.662  0.631  -6.789 "H6'2" DM1 66 
DM1 "H6'3" 3H6* H 0 0 N N N 12.732 6.739  9.134  0.068  -1.045 -6.726 "H6'3" DM1 67 
# 
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 
DM1 C1    C2     DOUB Y N 1  
DM1 C1    C20    SING Y N 2  
DM1 C1    H1     SING N N 3  
DM1 C2    C3     SING Y N 4  
DM1 C2    H2     SING N N 5  
DM1 C3    C4     DOUB Y N 6  
DM1 C3    H3     SING N N 7  
DM1 C4    O4     SING N N 8  
DM1 C4    C5     SING Y N 9  
DM1 O4    C21    SING N N 10 
DM1 C5    C6     SING N N 11 
DM1 C5    C20    DOUB Y N 12 
DM1 C6    O6     DOUB N N 13 
DM1 C6    C7     SING N N 14 
DM1 C7    C8     DOUB Y N 15 
DM1 C7    C18    SING Y N 16 
DM1 C8    O8     SING N N 17 
DM1 C8    C9     SING Y N 18 
DM1 O8    HO8    SING N N 19 
DM1 C9    C10    SING N N 20 
DM1 C9    C16    DOUB Y N 21 
DM1 C10   O10    SING N N 22 
DM1 C10   C11    SING N N 23 
DM1 C10   H10    SING N N 24 
DM1 O10   "C1'"  SING N N 25 
DM1 C11   C12    SING N N 26 
DM1 C11   H111   SING N N 27 
DM1 C11   H112   SING N N 28 
DM1 C12   O12    SING N N 29 
DM1 C12   C13    SING N N 30 
DM1 C12   C15    SING N N 31 
DM1 O12   HO12   SING N N 32 
DM1 C13   O13    DOUB N N 33 
DM1 C13   C14    SING N N 34 
DM1 C14   H141   SING N N 35 
DM1 C14   H142   SING N N 36 
DM1 C14   H143   SING N N 37 
DM1 C15   C16    SING N N 38 
DM1 C15   H151   SING N N 39 
DM1 C15   H152   SING N N 40 
DM1 C16   C17    SING Y N 41 
DM1 C17   O17    SING N N 42 
DM1 C17   C18    DOUB Y N 43 
DM1 O17   HO17   SING N N 44 
DM1 C18   C19    SING N N 45 
DM1 C19   O19    DOUB N N 46 
DM1 C19   C20    SING N N 47 
DM1 C21   H211   SING N N 48 
DM1 C21   H212   SING N N 49 
DM1 C21   H213   SING N N 50 
DM1 "C1'" "C2'"  SING N N 51 
DM1 "C1'" "O5'"  SING N N 52 
DM1 "C1'" "H1'"  SING N N 53 
DM1 "C2'" "C3'"  SING N N 54 
DM1 "C2'" "H2'1" SING N N 55 
DM1 "C2'" "H2'2" SING N N 56 
DM1 "C3'" "N3'"  SING N N 57 
DM1 "C3'" "C4'"  SING N N 58 
DM1 "C3'" "H3'"  SING N N 59 
DM1 "N3'" "HN'1" SING N N 60 
DM1 "N3'" "HN'2" SING N N 61 
DM1 "C4'" "O4'"  SING N N 62 
DM1 "C4'" "C5'"  SING N N 63 
DM1 "C4'" "H4'"  SING N N 64 
DM1 "O4'" "HO4'" SING N N 65 
DM1 "C5'" "O5'"  SING N N 66 
DM1 "C5'" "C6'"  SING N N 67 
DM1 "C5'" "H5'"  SING N N 68 
DM1 "C6'" "H6'1" SING N N 69 
DM1 "C6'" "H6'2" SING N N 70 
DM1 "C6'" "H6'3" SING N N 71 
# 
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 
DM1 SMILES           ACDLabs              10.04 O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)C)CC5OC4OC(C(O)C(N)C4)C 
DM1 InChI            InChI                1.02b 
InChI=1/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1 
DM1 InChIKey         InChI                1.02b STQGQHZAVUOBTE-VGBVRHCVBQ 
DM1 SMILES_CANONICAL CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O 
DM1 SMILES           CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH](N)[CH](O)[CH](C)O5)c4c(O)c3C(=O)c12)C(C)=O 
DM1 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)C)O)N)O 
DM1 SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)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 
DM1 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" 
DM1 "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-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione     
# 
