data_DM8
# 
_chem_comp.id                                    DM8 
_chem_comp.name                                  "2'-BROMO-4'-EPIDAUNORUBICIN" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H28 Br N O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "WP401; DAUNOMYCIN DERIVATIVE; DAUNORUBICIN DERIVATIVE" 
_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                        606.416 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM8 
_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        288D 
_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 
DM8 C1     C1   C  0 1 Y N N 15.274 18.233 5.160  0.065  0.259  -6.672 C1     DM8 1  
DM8 C2     C2   C  0 1 Y N N 16.433 18.990 5.192  1.231  -0.077 -7.342 C2     DM8 2  
DM8 C3     C3   C  0 1 Y N N 17.770 18.382 5.139  2.396  -0.319 -6.644 C3     DM8 3  
DM8 C4     C4   C  0 1 Y N N 17.843 16.929 5.032  2.418  -0.229 -5.255 C4     DM8 4  
DM8 C5     C5   C  0 1 N N N 16.674 14.730 4.915  1.248  0.210  -3.095 C5     DM8 5  
DM8 C6     C6   C  0 1 Y N N 15.426 12.608 4.888  -0.100 0.070  -1.002 C6     DM8 6  
DM8 C7     C7   C  0 1 N N S 14.139 10.412 4.808  -1.314 -0.107 1.158  C7     DM8 7  
DM8 C8     C8   C  0 1 N N N 12.801 9.789  4.728  -2.609 0.393  1.793  C8     DM8 8  
DM8 C9     C9   C  0 1 N N S 11.663 10.538 5.336  -3.789 -0.207 1.020  C9     DM8 9  
DM8 C10    C10  C  0 1 N N N 11.604 12.036 4.877  -3.835 0.438  -0.362 C10    DM8 10 
DM8 C11    C11  C  0 1 Y N N 12.975 14.015 4.941  -2.441 0.559  -2.416 C11    DM8 11 
DM8 C12    C12  C  0 1 N N N 14.125 16.183 5.059  -1.171 0.712  -4.556 C12    DM8 12 
DM8 C13    C13  C  0 1 N N N 10.342 9.899  4.963  -3.600 -1.696 0.880  C13    DM8 13 
DM8 C14    C14  C  0 1 N N N 10.005 8.931  5.801  -4.053 -2.620 1.980  C14    DM8 14 
DM8 C15    C15  C  0 1 Y N N 15.409 16.834 5.075  0.064  0.354  -5.286 C15    DM8 15 
DM8 C16    C16  C  0 1 Y N N 16.626 16.234 5.000  1.249  0.103  -4.567 C16    DM8 16 
DM8 C17    C17  C  0 1 Y N N 15.398 14.004 4.947  -0.039 0.263  -2.379 C17    DM8 17 
DM8 C18    C18  C  0 1 Y N N 14.122 14.753 4.963  -1.228 0.509  -3.097 C18    DM8 18 
DM8 C19    C19  C  0 1 Y N N 12.913 12.616 4.899  -2.485 0.363  -1.029 C19    DM8 19 
DM8 C20    C20  C  0 1 Y N N 14.147 11.988 4.851  -1.329 0.119  -0.331 C20    DM8 20 
DM8 C21    C21  C  0 1 N N N 20.319 16.808 5.011  4.565  -0.784 -5.546 C21    DM8 21 
DM8 O4     O4   O  0 1 N N N 19.021 16.304 4.995  3.566  -0.468 -4.574 O4     DM8 22 
DM8 O5     O5   O  0 1 N N N 17.711 14.049 4.856  2.296  0.249  -2.479 O5     DM8 23 
DM8 O6     O6   O  0 1 N N N 16.522 11.918 4.845  1.038  -0.167 -0.305 O6     DM8 24 
DM8 O7     O7   O  0 1 N N N 14.812 10.154 6.083  -0.207 0.594  1.729  O7     DM8 25 
DM8 O9     O9   O  0 1 N N N 11.685 10.527 6.814  -5.007 0.059  1.717  O9     DM8 26 
DM8 O11    O11  O  0 1 N N N 11.778 14.756 5.000  -3.588 0.799  -3.098 O11    DM8 27 
DM8 O12    O12  O  0 1 N N N 13.090 16.892 5.080  -2.128 1.167  -5.153 O12    DM8 28 
DM8 O13    O13  O  0 1 N N N 9.358  10.261 3.922  -3.085 -2.148 -0.114 O13    DM8 29 
DM8 "C1'"  C1*  C  0 1 N N R 15.734 9.125  6.217  0.516  -0.349 2.520  "C1'"  DM8 30 
DM8 "C2'"  C2*  C  0 1 N N R 16.374 9.178  7.631  1.874  0.243  2.903  "C2'"  DM8 31 
DM8 "C3'"  C3*  C  0 1 N N R 15.317 8.898  8.650  1.651  1.543  3.681  "C3'"  DM8 32 
DM8 "C4'"  C4*  C  0 1 N N R 14.669 7.490  8.437  0.711  1.255  4.857  "C4'"  DM8 33 
DM8 "C5'"  C5*  C  0 1 N N S 13.895 7.563  7.065  -0.559 0.586  4.327  "C5'"  DM8 34 
DM8 "C6'"  C6*  C  0 1 N N N 13.306 6.228  6.622  -1.518 0.325  5.491  "C6'"  DM8 35 
DM8 "O5'"  O5*  O  0 1 N N N 14.958 7.857  6.030  -0.228 -0.650 3.699  "O5'"  DM8 36 
DM8 "O4'"  O4*  O  0 1 N N N 13.738 7.215  9.515  0.369  2.479  5.510  "O4'"  DM8 37 
DM8 "N3'"  N3*  N  0 1 N N N 15.872 8.945  10.107 2.935  2.045  4.189  "N3'"  DM8 38 
DM8 BR     BR   BR 0 0 N N N 17.849 8.110  7.610  2.859  -1.034 4.027  BR     DM8 39 
DM8 H1     H1   H  0 1 N N N 14.286 18.722 5.200  -0.841 0.448  -7.227 H1     DM8 40 
DM8 H2     H2   H  0 1 N N N 16.290 20.081 5.260  1.227  -0.150 -8.419 H2     DM8 41 
DM8 H3     H3   H  0 1 N N N 18.686 18.994 5.178  3.298  -0.580 -7.179 H3     DM8 42 
DM8 H7     H7   H  0 1 N N N 14.614 9.978  3.897  -1.204 -1.173 1.358  H7     DM8 43 
DM8 H81    1H8  H  0 1 N N N 12.564 9.554  3.663  -2.649 1.480  1.737  H81    DM8 44 
DM8 H82    2H8  H  0 1 N N N 12.843 8.762  5.161  -2.653 0.076  2.835  H82    DM8 45 
DM8 H101   1H10 H  0 0 N N N 11.117 12.146 3.879  -4.128 1.483  -0.260 H101   DM8 46 
DM8 H102   2H10 H  0 0 N N N 10.877 12.627 5.481  -4.569 -0.082 -0.977 H102   DM8 47 
DM8 H141   1H14 H  0 0 N N N 9.032  8.460  5.526  -3.835 -3.651 1.701  H141   DM8 48 
DM8 H142   2H14 H  0 0 N N N 10.814 8.168  5.884  -3.526 -2.374 2.902  H142   DM8 49 
DM8 H143   3H14 H  0 0 N N N 9.995  9.293  6.855  -5.126 -2.504 2.133  H143   DM8 50 
DM8 H211   1H21 H  0 0 N N N 21.303 16.285 4.980  5.510  -0.985 -5.043 H211   DM8 51 
DM8 H212   2H21 H  0 0 N N N 20.353 17.532 4.164  4.258  -1.666 -6.109 H212   DM8 52 
DM8 H213   3H21 H  0 0 N N N 20.364 17.448 5.922  4.687  0.056  -6.228 H213   DM8 53 
DM8 H6     H6   H  0 1 N N N 16.541 10.969 4.804  1.139  -1.127 -0.253 H6     DM8 54 
DM8 H9     H9   H  0 1 N N N 10.960 11.003 7.201  -5.722 -0.319 1.187  H9     DM8 55 
DM8 H11    H11  H  0 1 N N N 10.979 14.242 4.984  -3.936 -0.061 -3.371 H11    DM8 56 
DM8 "H1'"  H1*  H  0 1 N N N 16.562 9.201  5.475  0.669  -1.263 1.945  "H1'"  DM8 57 
DM8 "H2'"  H2*  H  0 1 N N N 16.758 10.181 7.929  2.447  0.452  2.000  "H2'"  DM8 58 
DM8 "H3'"  H3*  H  0 1 N N N 14.554 9.700  8.513  1.200  2.289  3.027  "H3'"  DM8 59 
DM8 "H4'"  H4*  H  0 1 N N N 15.436 6.681  8.427  1.205  0.589  5.565  "H4'"  DM8 60 
DM8 "H5'"  H5*  H  0 1 N N N 13.070 8.305  7.172  -1.039 1.243  3.603  "H5'"  DM8 61 
DM8 "H6'1" 1H6* H  0 0 N N N 12.758 6.279  5.651  -2.425 -0.146 5.115  "H6'1" DM8 62 
DM8 "H6'2" 2H6* H  0 0 N N N 14.095 5.441  6.586  -1.039 -0.334 6.215  "H6'2" DM8 63 
DM8 "H6'3" 3H6* H  0 0 N N N 12.653 5.801  7.419  -1.771 1.269  5.972  "H6'3" DM8 64 
DM8 "HO4'" *HO4 H  0 0 N N N 13.344 6.360  9.385  -0.226 2.252  6.237  "HO4'" DM8 65 
DM8 "HN'1" 1HN* H  0 0 N N N 15.150 8.753  10.802 3.517  2.219  3.383  "HN'1" DM8 66 
DM8 "HN'2" 2HN* H  0 0 N N N 16.338 9.832  10.294 2.749  2.942  4.612  "HN'2" DM8 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 
DM8 C1    C2     DOUB Y N 1  
DM8 C1    C15    SING Y N 2  
DM8 C1    H1     SING N N 3  
DM8 C2    C3     SING Y N 4  
DM8 C2    H2     SING N N 5  
DM8 C3    C4     DOUB Y N 6  
DM8 C3    H3     SING N N 7  
DM8 C4    C16    SING Y N 8  
DM8 C4    O4     SING N N 9  
DM8 C5    C16    SING N N 10 
DM8 C5    C17    SING N N 11 
DM8 C5    O5     DOUB N N 12 
DM8 C6    C17    DOUB Y N 13 
DM8 C6    C20    SING Y N 14 
DM8 C6    O6     SING N N 15 
DM8 C7    C8     SING N N 16 
DM8 C7    C20    SING N N 17 
DM8 C7    O7     SING N N 18 
DM8 C7    H7     SING N N 19 
DM8 C8    C9     SING N N 20 
DM8 C8    H81    SING N N 21 
DM8 C8    H82    SING N N 22 
DM8 C9    C10    SING N N 23 
DM8 C9    C13    SING N N 24 
DM8 C9    O9     SING N N 25 
DM8 C10   C19    SING N N 26 
DM8 C10   H101   SING N N 27 
DM8 C10   H102   SING N N 28 
DM8 C11   C18    DOUB Y N 29 
DM8 C11   C19    SING Y N 30 
DM8 C11   O11    SING N N 31 
DM8 C12   C15    SING N N 32 
DM8 C12   C18    SING N N 33 
DM8 C12   O12    DOUB N N 34 
DM8 C13   C14    SING N N 35 
DM8 C13   O13    DOUB N N 36 
DM8 C14   H141   SING N N 37 
DM8 C14   H142   SING N N 38 
DM8 C14   H143   SING N N 39 
DM8 C15   C16    DOUB Y N 40 
DM8 C17   C18    SING Y N 41 
DM8 C19   C20    DOUB Y N 42 
DM8 C21   O4     SING N N 43 
DM8 C21   H211   SING N N 44 
DM8 C21   H212   SING N N 45 
DM8 C21   H213   SING N N 46 
DM8 O6    H6     SING N N 47 
DM8 O7    "C1'"  SING N N 48 
DM8 O9    H9     SING N N 49 
DM8 O11   H11    SING N N 50 
DM8 "C1'" "C2'"  SING N N 51 
DM8 "C1'" "O5'"  SING N N 52 
DM8 "C1'" "H1'"  SING N N 53 
DM8 "C2'" "C3'"  SING N N 54 
DM8 "C2'" BR     SING N N 55 
DM8 "C2'" "H2'"  SING N N 56 
DM8 "C3'" "C4'"  SING N N 57 
DM8 "C3'" "N3'"  SING N N 58 
DM8 "C3'" "H3'"  SING N N 59 
DM8 "C4'" "C5'"  SING N N 60 
DM8 "C4'" "O4'"  SING N N 61 
DM8 "C4'" "H4'"  SING N N 62 
DM8 "C5'" "C6'"  SING N N 63 
DM8 "C5'" "O5'"  SING N N 64 
DM8 "C5'" "H5'"  SING N N 65 
DM8 "C6'" "H6'1" SING N N 66 
DM8 "C6'" "H6'2" SING N N 67 
DM8 "C6'" "H6'3" SING N N 68 
DM8 "O4'" "HO4'" SING N N 69 
DM8 "N3'" "HN'1" SING N N 70 
DM8 "N3'" "HN'2" 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 
DM8 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)C4Br)C 
DM8 InChI            InChI                1.02b 
InChI=1/C27H28BrNO10/c1-9-21(31)20(29)19(28)26(38-9)39-14-8-27(36,10(2)30)7-12-16(14)25(35)18-17(23(12)33)22(32)11-5-4-6-13(37-3)15(11)24(18)34/h4-6,9,14,19-21,26,31,33,35-36H,7-8,29H2,1-3H3/t9-,14-,19+,20-,21-,26-,27-/m0/s1 
DM8 InChIKey         InChI                1.02b RNTSDANIDLGPLQ-VQBVCDDFBV 
DM8 SMILES_CANONICAL CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](N)[C@H]5Br)c4c(O)c3C(=O)c12)C(C)=O 
DM8 SMILES           CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5O[CH](C)[CH](O)[CH](N)[CH]5Br)c4c(O)c3C(=O)c12)C(C)=O 
DM8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)Br)N)O 
DM8 SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(C(C(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)Br)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 
DM8 "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-bromo-2,3,6-trideoxy-alpha-L-mannopyranoside"    
DM8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (7S,9S)-7-[(2R,3R,4R,5R,6S)-4-amino-3-bromo-5-hydroxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione 
# 
