data_DM4
# 
_chem_comp.id                                    DM4 
_chem_comp.name                                  1-O-DEMETHYL-6-DEOXYDOXORUBICIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C26 H27 N O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        513.493 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM4 
_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        1D37 
_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 
DM4 C1     C1   C 0 1 Y N N 15.214 18.399 4.953  -6.320 0.365  -0.892 C1     DM4 1  
DM4 C2     C2   C 0 1 Y N N 16.392 19.219 4.905  -7.190 -0.689 -0.664 C2     DM4 2  
DM4 C3     C3   C 0 1 Y N N 17.711 18.630 4.841  -6.762 -1.823 -0.005 C3     DM4 3  
DM4 C4     C4   C 0 1 Y N N 17.846 17.187 4.820  -5.447 -1.924 0.441  C4     DM4 4  
DM4 O4     O4   O 0 1 N N N 19.007 16.547 4.846  -5.031 -3.041 1.089  O4     DM4 5  
DM4 C5     C5   C 0 1 Y N N 16.649 16.451 4.868  -4.558 -0.870 0.218  C5     DM4 6  
DM4 C6     C6   C 0 1 N N N 16.730 14.969 4.868  -3.160 -0.955 0.680  C6     DM4 7  
DM4 O6     O6   O 0 1 N N N 17.762 14.276 4.799  -2.824 -1.817 1.470  O6     DM4 8  
DM4 C7     C7   C 0 1 Y N N 15.488 14.186 4.921  -2.172 0.017  0.173  C7     DM4 9  
DM4 C8     C8   C 0 1 Y N N 15.547 12.819 4.894  -0.806 -0.191 0.353  C8     DM4 10 
DM4 O8     O8   O 0 1 N N N 16.683 12.179 4.830  -0.372 -1.299 1.002  O8     DM4 11 
DM4 C9     C9   C 0 1 Y N N 14.335 12.126 4.921  0.120  0.739  -0.137 C9     DM4 12 
DM4 C10    C10  C 0 1 N N S 14.389 10.548 4.862  1.580  0.451  0.098  C10    DM4 13 
DM4 O10    O10  O 0 1 N N N 15.127 10.353 6.079  1.832  -0.935 -0.141 O10    DM4 14 
DM4 C11    C11  C 0 1 N N N 13.132 9.838  4.809  2.450  1.290  -0.836 C11    DM4 15 
DM4 C12    C12  C 0 1 N N S 11.903 10.514 5.357  2.013  2.754  -0.717 C12    DM4 16 
DM4 O12    O12  O 0 1 N N N 11.979 10.537 6.834  2.945  3.592  -1.403 O12    DM4 17 
DM4 C13    C13  C 0 1 N N N 10.635 9.781  4.969  1.949  3.149  0.736  C13    DM4 18 
DM4 O13    O13  O 0 1 N N N 9.860  10.396 4.150  0.909  3.058  1.342  O13    DM4 19 
DM4 C14    C14  C 0 1 N N N 9.821  8.722  5.787  3.185  3.657  1.433  C14    DM4 20 
DM4 O14    O14  O 0 1 N N N 8.885  7.513  5.532  2.873  3.963  2.794  O14    DM4 21 
DM4 C15    C15  C 0 1 N N N 11.802 12.078 4.963  0.630  2.896  -1.350 C15    DM4 22 
DM4 C16    C16  C 0 1 Y N N 13.090 12.723 4.915  -0.317 1.863  -0.796 C16    DM4 23 
DM4 C17    C17  C 0 1 Y N N 13.081 14.079 4.931  -1.682 2.083  -0.976 C17    DM4 24 
DM4 C18    C18  C 0 1 Y N N 14.194 14.893 4.953  -2.613 1.174  -0.500 C18    DM4 25 
DM4 C19    C19  C 0 1 N N N 14.166 16.327 4.995  -4.062 1.401  -0.691 C19    DM4 26 
DM4 O19    O19  O 0 1 N N N 13.138 17.026 5.000  -4.473 2.491  -1.037 O19    DM4 27 
DM4 C20    C20  C 0 1 Y N N 15.389 17.052 4.947  -5.003 0.285  -0.455 C20    DM4 28 
DM4 "C1'"  C1*  C 0 1 N N R 15.978 9.297  6.377  2.791  -1.354 0.831  "C1'"  DM4 29 
DM4 "C2'"  C2*  C 0 1 N N N 17.069 9.688  7.344  2.841  -2.883 0.869  "C2'"  DM4 30 
DM4 "C3'"  C3*  C 0 1 N N S 16.432 10.145 8.678  3.216  -3.405 -0.523 "C3'"  DM4 31 
DM4 "N3'"  N3*  N 0 1 N N N 17.565 10.390 9.682  3.416  -4.859 -0.467 "N3'"  DM4 32 
DM4 "C4'"  C4*  C 0 1 N N S 15.485 9.032  9.214  4.513  -2.721 -0.969 "C4'"  DM4 33 
DM4 "O4'"  O4*  O 0 1 N N N 16.401 7.935  9.438  5.588  -3.137 -0.125 "O4'"  DM4 34 
DM4 "C5'"  C5*  C 0 1 N N S 14.397 8.716  8.189  4.336  -1.204 -0.869 "C5'"  DM4 35 
DM4 "O5'"  O5*  O 0 1 N N N 15.110 8.212  6.919  4.075  -0.837 0.485  "O5'"  DM4 36 
DM4 "C6'"  C6*  C 0 1 N N N 13.439 7.513  8.540  5.614  -0.510 -1.346 "C6'"  DM4 37 
DM4 H1     H1   H 0 1 N N N 14.227 18.836 4.992  -6.665 1.249  -1.408 H1     DM4 38 
DM4 H2     H2   H 0 1 N N N 16.291 20.294 4.917  -8.213 -0.622 -1.006 H2     DM4 39 
DM4 H3     H3   H 0 1 N N N 18.588 19.260 4.809  -7.451 -2.637 0.166  H3     DM4 40 
DM4 HO4    HO4  H 0 1 N N N 19.305 16.394 3.957  -4.700 -3.649 0.414  HO4    DM4 41 
DM4 HO8    HO8  H 0 1 N N N 16.909 12.024 3.920  -0.327 -2.008 0.346  HO8    DM4 42 
DM4 H10    H10  H 0 1 N N N 14.817 10.141 3.934  1.831  0.689  1.132  H10    DM4 43 
DM4 H111   1H11 H 0 0 N N N 13.281 8.965  5.462  3.497  1.194  -0.548 H111   DM4 44 
DM4 H112   2H11 H 0 0 N N N 12.931 9.634  3.747  2.319  0.950  -1.864 H112   DM4 45 
DM4 HO12   2HO1 H 0 0 N N N 12.890 10.542 7.105  2.630  4.501  -1.302 HO12   DM4 46 
DM4 H141   1H14 H 0 0 N N N 8.995  9.414  6.009  3.961  2.892  1.402  H141   DM4 47 
DM4 H142   2H14 H 0 0 N N N 10.631 8.235  6.349  3.542  4.556  0.931  H142   DM4 48 
DM4 HO14   4HO1 H 0 0 N N N 8.694  7.450  4.604  3.688  4.283  3.202  HO14   DM4 49 
DM4 H151   1H15 H 0 0 N N N 11.205 12.580 5.739  0.239  3.892  -1.140 H151   DM4 50 
DM4 H152   2H15 H 0 0 N N N 11.337 12.157 3.969  0.714  2.765  -2.429 H152   DM4 51 
DM4 H17    H17  H 0 1 N N N 12.116 14.565 4.926  -2.016 2.971  -1.493 H17    DM4 52 
DM4 "H1'"  H1*  H 0 1 N N N 16.516 8.964  5.477  2.502  -0.977 1.812  "H1'"  DM4 53 
DM4 "H2'1" 1H2* H 0 0 N N N 17.661 10.511 6.918  3.589  -3.206 1.593  "H2'1" DM4 54 
DM4 "H2'2" 2H2* H 0 0 N N N 17.725 8.824  7.527  1.863  -3.273 1.153  "H2'2" DM4 55 
DM4 "H3'"  H3*  H 0 1 N N N 15.846 11.064 8.530  2.417  -3.172 -1.228 "H3'"  DM4 56 
DM4 "HN'1" 1HN* H 0 0 N N N 17.401 11.249 10.166 2.543  -5.260 -0.158 "HN'1" DM4 57 
DM4 "HN'2" 2HN* H 0 0 N N N 18.437 10.443 9.195  3.557  -5.169 -1.417 "HN'2" DM4 58 
DM4 "H4'"  H4*  H 0 1 N N N 14.925 9.296  10.123 4.733  -2.993 -2.001 "H4'"  DM4 59 
DM4 "HO4'" *HO4 H 0 0 N N N 16.602 7.515  8.610  6.382  -2.685 -0.440 "HO4'" DM4 60 
DM4 "H5'"  H5*  H 0 1 N N N 13.804 9.639  8.116  3.500  -0.894 -1.496 "H5'"  DM4 61 
DM4 "H6'1" 1H6* H 0 0 N N N 12.503 7.903  8.966  6.451  -0.819 -0.719 "H6'1" DM4 62 
DM4 "H6'2" 2H6* H 0 0 N N N 13.930 6.855  9.272  5.813  -0.788 -2.381 "H6'2" DM4 63 
DM4 "H6'3" 3H6* H 0 0 N N N 13.216 6.943  7.626  5.488  0.570  -1.277 "H6'3" DM4 64 
# 
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 
DM4 C1    C2     DOUB Y N 1  
DM4 C1    C20    SING Y N 2  
DM4 C1    H1     SING N N 3  
DM4 C2    C3     SING Y N 4  
DM4 C2    H2     SING N N 5  
DM4 C3    C4     DOUB Y N 6  
DM4 C3    H3     SING N N 7  
DM4 C4    O4     SING N N 8  
DM4 C4    C5     SING Y N 9  
DM4 O4    HO4    SING N N 10 
DM4 C5    C6     SING N N 11 
DM4 C5    C20    DOUB Y N 12 
DM4 C6    O6     DOUB N N 13 
DM4 C6    C7     SING N N 14 
DM4 C7    C8     DOUB Y N 15 
DM4 C7    C18    SING Y N 16 
DM4 C8    O8     SING N N 17 
DM4 C8    C9     SING Y N 18 
DM4 O8    HO8    SING N N 19 
DM4 C9    C10    SING N N 20 
DM4 C9    C16    DOUB Y N 21 
DM4 C10   O10    SING N N 22 
DM4 C10   C11    SING N N 23 
DM4 C10   H10    SING N N 24 
DM4 O10   "C1'"  SING N N 25 
DM4 C11   C12    SING N N 26 
DM4 C11   H111   SING N N 27 
DM4 C11   H112   SING N N 28 
DM4 C12   O12    SING N N 29 
DM4 C12   C13    SING N N 30 
DM4 C12   C15    SING N N 31 
DM4 O12   HO12   SING N N 32 
DM4 C13   O13    DOUB N N 33 
DM4 C13   C14    SING N N 34 
DM4 C14   O14    SING N N 35 
DM4 C14   H141   SING N N 36 
DM4 C14   H142   SING N N 37 
DM4 O14   HO14   SING N N 38 
DM4 C15   C16    SING N N 39 
DM4 C15   H151   SING N N 40 
DM4 C15   H152   SING N N 41 
DM4 C16   C17    SING Y N 42 
DM4 C17   C18    DOUB Y N 43 
DM4 C17   H17    SING N N 44 
DM4 C18   C19    SING N N 45 
DM4 C19   O19    DOUB N N 46 
DM4 C19   C20    SING N N 47 
DM4 "C1'" "C2'"  SING N N 48 
DM4 "C1'" "O5'"  SING N N 49 
DM4 "C1'" "H1'"  SING N N 50 
DM4 "C2'" "C3'"  SING N N 51 
DM4 "C2'" "H2'1" SING N N 52 
DM4 "C2'" "H2'2" SING N N 53 
DM4 "C3'" "N3'"  SING N N 54 
DM4 "C3'" "C4'"  SING N N 55 
DM4 "C3'" "H3'"  SING N N 56 
DM4 "N3'" "HN'1" SING N N 57 
DM4 "N3'" "HN'2" SING N N 58 
DM4 "C4'" "O4'"  SING N N 59 
DM4 "C4'" "C5'"  SING N N 60 
DM4 "C4'" "H4'"  SING N N 61 
DM4 "O4'" "HO4'" SING N N 62 
DM4 "C5'" "O5'"  SING N N 63 
DM4 "C5'" "C6'"  SING N N 64 
DM4 "C5'" "H5'"  SING N N 65 
DM4 "C6'" "H6'1" SING N N 66 
DM4 "C6'" "H6'2" SING N N 67 
DM4 "C6'" "H6'3" SING N N 68 
# 
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 
DM4 SMILES           ACDLabs              10.04 O=C2c1cc5c(c(O)c1C(=O)c3c2cccc3O)C(OC4OC(C(O)C(N)C4)C)CC(O)(C(=O)CO)C5 
DM4 InChI            InChI                1.02b 
InChI=1/C26H27NO10/c1-10-22(31)14(27)6-18(36-10)37-16-8-26(35,17(30)9-28)7-11-5-13-21(24(33)19(11)16)25(34)20-12(23(13)32)3-2-4-15(20)29/h2-5,10,14,16,18,22,28-29,31,33,35H,6-9,27H2,1H3/t10-,14-,16-,18-,22+,26-/m0/s1 
DM4 InChIKey         InChI                1.02b ROILTUODAPUWLG-NRFWZUBKBT 
DM4 SMILES_CANONICAL CACTVS               3.341 C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(Cc3cc4C(=O)c5cccc(O)c5C(=O)c4c(O)c23)C(=O)CO 
DM4 SMILES           CACTVS               3.341 C[CH]1O[CH](C[CH](N)[CH]1O)O[CH]2C[C](O)(Cc3cc4C(=O)c5cccc(O)c5C(=O)c4c(O)c23)C(=O)CO 
DM4 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(c3)C(=O)c5cccc(c5C4=O)O)O)(C(=O)CO)O)N)O 
DM4 SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3)C(=O)c5cccc(c5C4=O)O)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 
DM4 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3S)-3,10,12-trihydroxy-3-(hydroxyacetyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" 
DM4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-4,6,9-trihydroxy-9-(2-hydroxyethanoyl)-8,10-dihydro-7H-tetracene-5,12-dione    
# 
