data_DM2
# 
_chem_comp.id                                    DM2 
_chem_comp.name                                  DOXORUBICIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H29 N O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ADRIAMYCIN 
_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                        543.519 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM2 
_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        151D 
_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 
DM2 C1     C1   C 0 1 Y N N 15.226 18.450 4.896  -0.791 -0.376 6.114  C1     DM2 1  
DM2 C2     C2   C 0 1 Y N N 16.429 19.161 4.909  0.106  0.151  7.027  C2     DM2 2  
DM2 C3     C3   C 0 1 Y N N 17.654 18.469 4.880  1.331  0.630  6.611  C3     DM2 3  
DM2 C4     C4   C 0 1 Y N N 17.677 17.063 4.829  1.682  0.590  5.264  C4     DM2 4  
DM2 O4     O4   O 0 1 N N N 18.898 16.388 4.808  2.887  1.062  4.859  O4     DM2 5  
DM2 C5     C5   C 0 1 Y N N 16.456 16.353 4.816  0.784  0.066  4.332  C5     DM2 6  
DM2 C6     C6   C 0 1 N N N 16.409 14.946 4.803  1.136  0.008  2.900  C6     DM2 7  
DM2 O6     O6   O 0 1 N N N 17.561 14.211 4.771  2.284  0.186  2.539  O6     DM2 8  
DM2 C7     C7   C 0 1 Y N N 15.196 14.209 4.817  0.076  -0.262 1.910  C7     DM2 9  
DM2 C8     C8   C 0 1 Y N N 15.164 12.808 4.784  0.293  -0.040 0.553  C8     DM2 10 
DM2 O8     O8   O 0 1 N N N 16.295 12.032 4.788  1.493  0.428  0.131  O8     DM2 11 
DM2 C9     C9   C 0 1 Y N N 13.929 12.131 4.758  -0.721 -0.297 -0.379 C9     DM2 12 
DM2 C10    C10  C 0 1 N N S 13.995 10.639 4.786  -0.413 -0.024 -1.829 C10    DM2 13 
DM2 O10    O10  O 0 1 N N N 14.592 10.397 6.123  0.906  -0.487 -2.124 O10    DM2 14 
DM2 C11    C11  C 0 1 N N N 12.711 9.868  4.523  -1.412 -0.739 -2.736 C11    DM2 15 
DM2 C12    C12  C 0 1 N N S 11.569 10.600 5.359  -2.828 -0.395 -2.259 C12    DM2 16 
DM2 O12    O12  O 0 1 N N N 11.611 10.753 6.835  -3.784 -0.864 -3.212 O12    DM2 17 
DM2 C13    C13  C 0 1 N N N 10.269 9.864  5.071  -2.962 1.096  -2.096 C13    DM2 18 
DM2 O13    O13  O 0 1 N N N 9.543  10.187 3.954  -2.780 1.605  -1.016 O13    DM2 19 
DM2 C14    C14  C 0 1 N N N 9.825  8.804  6.033  -3.323 1.954  -3.282 C14    DM2 20 
DM2 O14    O14  O 0 1 N N N 8.617  8.191  5.670  -3.389 3.323  -2.877 O14    DM2 21 
DM2 C15    C15  C 0 1 N N N 11.432 12.065 4.766  -3.061 -1.082 -0.915 C15    DM2 22 
DM2 C16    C16  C 0 1 Y N N 12.729 12.807 4.799  -1.936 -0.777 0.039  C16    DM2 23 
DM2 C17    C17  C 0 1 Y N N 12.761 14.224 4.827  -2.170 -1.005 1.402  C17    DM2 24 
DM2 O17    O17  O 0 1 N N N 11.570 14.889 4.797  -3.374 -1.478 1.809  O17    DM2 25 
DM2 C18    C18  C 0 1 Y N N 13.985 14.924 4.822  -1.174 -0.751 2.341  C18    DM2 26 
DM2 C19    C19  C 0 1 N N N 14.007 16.349 4.853  -1.410 -0.985 3.778  C19    DM2 27 
DM2 O19    O19  O 0 1 N N N 12.853 16.988 4.878  -2.373 -1.630 4.146  O19    DM2 28 
DM2 C20    C20  C 0 1 Y N N 15.244 17.040 4.865  -0.462 -0.426 4.765  C20    DM2 29 
DM2 C21    C21  C 0 1 N N N 20.164 17.131 4.894  3.562  1.529  6.029  C21    DM2 30 
DM2 "C1'"  C1*  C 0 1 N N R 15.508 9.325  6.325  1.598  0.601  -2.737 "C1'"  DM2 31 
DM2 "C2'"  C2*  C 0 1 N N N 16.662 9.744  7.308  3.094  0.283  -2.798 "C2'"  DM2 32 
DM2 "C3'"  C3*  C 0 1 N N S 15.986 9.896  8.700  3.298  -1.006 -3.599 "C3'"  DM2 33 
DM2 "N3'"  N3*  N 0 1 N N N 17.069 10.218 9.702  4.735  -1.242 -3.796 "N3'"  DM2 34 
DM2 "C4'"  C4*  C 0 1 N N S 15.236 8.613  9.132  2.607  -0.854 -4.959 "C4'"  DM2 35 
DM2 "O4'"  O4*  O 0 1 N N N 16.324 7.597  9.201  3.273  0.154  -5.723 "O4'"  DM2 36 
DM2 "C5'"  C5*  C 0 1 N N S 14.150 8.254  8.082  1.148  -0.450 -4.735 "C5'"  DM2 37 
DM2 "O5'"  O5*  O 0 1 N N N 14.828 8.116  6.752  1.094  0.801  -4.056 "O5'"  DM2 38 
DM2 "C6'"  C6*  C 0 1 N N N 13.470 6.895  8.316  0.441  -0.326 -6.086 "C6'"  DM2 39 
DM2 H1     H1   H 0 1 N N N 14.268 18.998 4.910  -1.747 -0.749 6.450  H1     DM2 40 
DM2 H2     H2   H 0 1 N N N 16.411 20.263 4.942  -0.154 0.188  8.075  H2     DM2 41 
DM2 H3     H3   H 0 1 N N N 18.602 19.032 4.897  2.022  1.038  7.334  H3     DM2 42 
DM2 HO8    HO8  H 0 1 N N N 16.273 11.082 4.765  1.418  1.392  0.091  HO8    DM2 43 
DM2 H10    H10  H 0 1 N N N 14.584 10.240 3.927  -0.466 1.048  -2.011 H10    DM2 44 
DM2 H111   1H11 H 0 0 N N N 12.469 9.766  3.439  -1.256 -1.816 -2.677 H111   DM2 45 
DM2 H112   2H11 H 0 0 N N N 12.794 8.779  4.747  -1.279 -0.403 -3.764 H112   DM2 46 
DM2 HO12   2HO1 H 0 0 N N N 10.930 11.189 7.333  -4.658 -0.643 -2.862 HO12   DM2 47 
DM2 H141   1H14 H 0 0 N N N 10.626 8.042  6.178  -2.564 1.840  -4.057 H141   DM2 48 
DM2 H142   2H14 H 0 0 N N N 9.765  9.211  7.069  -4.291 1.643  -3.674 H142   DM2 49 
DM2 HO14   4HO1 H 0 0 N N N 8.335  7.519  6.279  -3.622 3.836  -3.663 HO14   DM2 50 
DM2 H151   1H15 H 0 0 N N N 11.003 12.046 3.737  -3.120 -2.160 -1.068 H151   DM2 51 
DM2 H152   2H15 H 0 0 N N N 10.625 12.636 5.282  -4.000 -0.729 -0.489 H152   DM2 52 
DM2 HO17   7HO1 H 0 0 N N N 11.591 15.838 4.815  -3.932 -0.707 1.985  HO17   DM2 53 
DM2 H211   1H21 H 0 0 N N N 21.139 16.591 4.877  4.541  1.920  5.752  H211   DM2 54 
DM2 H212   2H21 H 0 0 N N N 20.174 17.897 4.084  2.975  2.319  6.497  H212   DM2 55 
DM2 H213   3H21 H 0 0 N N N 20.133 17.768 5.808  3.686  0.704  6.731  H213   DM2 56 
DM2 "H1'"  H1*  H 0 1 N N N 15.984 9.090  5.344  1.444  1.506  -2.149 "H1'"  DM2 57 
DM2 "H2'1" 1H2* H 0 0 N N N 17.530 9.044  7.305  3.621  1.103  -3.286 "H2'1" DM2 58 
DM2 "H2'2" 2H2* H 0 0 N N N 17.223 10.650 6.980  3.480  0.150  -1.787 "H2'2" DM2 59 
DM2 "H3'"  H3*  H 0 1 N N N 15.225 10.709 8.646  2.860  -1.846 -3.059 "H3'"  DM2 60 
DM2 "HN'1" 1HN* H 0 0 N N N 16.625 10.317 10.615 5.144  -1.323 -2.877 "HN'1" DM2 61 
DM2 "HN'2" 2HN* H 0 0 N N N 17.623 11.032 9.439  4.823  -2.147 -4.233 "HN'2" DM2 62 
DM2 "H4'"  H4*  H 0 1 N N N 14.688 8.702  10.098 2.645  -1.802 -5.496 "H4'"  DM2 63 
DM2 "HO4'" *HO4 H 0 0 N N N 15.863 6.809  9.466  2.807  0.217  -6.568 "HO4'" DM2 64 
DM2 "H5'"  H5*  H 0 1 N N N 13.382 9.060  8.145  0.650  -1.210 -4.134 "H5'"  DM2 65 
DM2 "H6'1" 1H6* H 0 0 N N N 12.690 6.637  7.562  -0.597 -0.038 -5.927 "H6'1" DM2 66 
DM2 "H6'2" 2H6* H 0 0 N N N 14.232 6.083  8.381  0.940  0.432  -6.689 "H6'2" DM2 67 
DM2 "H6'3" 3H6* H 0 0 N N N 13.048 6.842  9.346  0.478  -1.284 -6.605 "H6'3" DM2 68 
# 
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 
DM2 C1    C2     DOUB Y N 1  
DM2 C1    C20    SING Y N 2  
DM2 C1    H1     SING N N 3  
DM2 C2    C3     SING Y N 4  
DM2 C2    H2     SING N N 5  
DM2 C3    C4     DOUB Y N 6  
DM2 C3    H3     SING N N 7  
DM2 C4    O4     SING N N 8  
DM2 C4    C5     SING Y N 9  
DM2 O4    C21    SING N N 10 
DM2 C5    C6     SING N N 11 
DM2 C5    C20    DOUB Y N 12 
DM2 C6    O6     DOUB N N 13 
DM2 C6    C7     SING N N 14 
DM2 C7    C8     DOUB Y N 15 
DM2 C7    C18    SING Y N 16 
DM2 C8    O8     SING N N 17 
DM2 C8    C9     SING Y N 18 
DM2 O8    HO8    SING N N 19 
DM2 C9    C10    SING N N 20 
DM2 C9    C16    DOUB Y N 21 
DM2 C10   O10    SING N N 22 
DM2 C10   C11    SING N N 23 
DM2 C10   H10    SING N N 24 
DM2 O10   "C1'"  SING N N 25 
DM2 C11   C12    SING N N 26 
DM2 C11   H111   SING N N 27 
DM2 C11   H112   SING N N 28 
DM2 C12   O12    SING N N 29 
DM2 C12   C13    SING N N 30 
DM2 C12   C15    SING N N 31 
DM2 O12   HO12   SING N N 32 
DM2 C13   O13    DOUB N N 33 
DM2 C13   C14    SING N N 34 
DM2 C14   O14    SING N N 35 
DM2 C14   H141   SING N N 36 
DM2 C14   H142   SING N N 37 
DM2 O14   HO14   SING N N 38 
DM2 C15   C16    SING N N 39 
DM2 C15   H151   SING N N 40 
DM2 C15   H152   SING N N 41 
DM2 C16   C17    SING Y N 42 
DM2 C17   O17    SING N N 43 
DM2 C17   C18    DOUB Y N 44 
DM2 O17   HO17   SING N N 45 
DM2 C18   C19    SING N N 46 
DM2 C19   O19    DOUB N N 47 
DM2 C19   C20    SING N N 48 
DM2 C21   H211   SING N N 49 
DM2 C21   H212   SING N N 50 
DM2 C21   H213   SING N N 51 
DM2 "C1'" "C2'"  SING N N 52 
DM2 "C1'" "O5'"  SING N N 53 
DM2 "C1'" "H1'"  SING N N 54 
DM2 "C2'" "C3'"  SING N N 55 
DM2 "C2'" "H2'1" SING N N 56 
DM2 "C2'" "H2'2" SING N N 57 
DM2 "C3'" "N3'"  SING N N 58 
DM2 "C3'" "C4'"  SING N N 59 
DM2 "C3'" "H3'"  SING N N 60 
DM2 "N3'" "HN'1" SING N N 61 
DM2 "N3'" "HN'2" SING N N 62 
DM2 "C4'" "O4'"  SING N N 63 
DM2 "C4'" "C5'"  SING N N 64 
DM2 "C4'" "H4'"  SING N N 65 
DM2 "O4'" "HO4'" SING N N 66 
DM2 "C5'" "O5'"  SING N N 67 
DM2 "C5'" "C6'"  SING N N 68 
DM2 "C5'" "H5'"  SING N N 69 
DM2 "C6'" "H6'1" SING N N 70 
DM2 "C6'" "H6'2" SING N N 71 
DM2 "C6'" "H6'3" SING N N 72 
# 
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 
DM2 SMILES           ACDLabs              10.04 O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)CO)CC5OC4OC(C(O)C(N)C4)C 
DM2 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/t10-,13-,15-,17-,22+,27-/m0/s1 
DM2 InChIKey         InChI                1.02b AOJJSUZBOXZQNB-TZSSRYMLBG 
DM2 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(=O)CO 
DM2 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(=O)CO 
DM2 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)O 
DM2 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)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 
DM2 "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-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" 
DM2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyethanoyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione   
# 
