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                   2021-03-01
_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  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"  
DM2  InChI             InChI                 1.03   "InChI=1S/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                 1.03   AOJJSUZBOXZQNB-TZSSRYMLSA-N  
#   #
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
DM2  "Create component"   1999-07-08  RCSB  
DM2  "Modify descriptor"  2011-06-04  RCSB  
DM2  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     DM2
_pdbx_chem_comp_synonyms.name        ADRIAMYCIN
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
