data_DM3
# 
_chem_comp.id                                    DM3 
_chem_comp.name                                  6-DEOXYDAUNOMYCIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H29 N O9" 
_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                        511.520 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DM3 
_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        1D14 
_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 
DM3 C1     C1   C 0 1 Y N N 9.002  21.100 33.532 -0.954 -0.438 6.081  C1     DM3 1  
DM3 C2     C2   C 0 1 Y N N 7.680  20.629 33.252 -0.020 0.017  6.998  C2     DM3 2  
DM3 C3     C3   C 0 1 Y N N 7.394  19.282 33.174 1.221  0.446  6.581  C3     DM3 3  
DM3 C4     C4   C 0 1 Y N N 8.420  18.382 33.345 1.556  0.427  5.229  C4     DM3 4  
DM3 O4     O4   O 0 1 N N N 8.168  17.010 33.262 2.779  0.849  4.824  O4     DM3 5  
DM3 C5     C5   C 0 1 Y N N 9.732  18.817 33.650 0.623  -0.023 4.293  C5     DM3 6  
DM3 C6     C6   C 0 1 N N N 10.789 17.952 33.814 0.957  -0.057 2.856  C6     DM3 7  
DM3 O6     O6   O 0 1 N N N 10.476 16.610 33.732 2.109  0.072  2.488  O6     DM3 8  
DM3 C7     C7   C 0 1 Y N N 12.086 18.417 34.093 -0.124 -0.246 1.870  C7     DM3 9  
DM3 C8     C8   C 0 1 Y N N 13.168 17.576 34.266 0.091  0.003  0.516  C8     DM3 10 
DM3 O8     O8   O 0 1 N N N 13.135 16.191 34.194 1.308  0.423  0.093  O8     DM3 11 
DM3 C9     C9   C 0 1 Y N N 14.425 18.170 34.564 -0.944 -0.177 -0.407 C9     DM3 12 
DM3 C10    C10  C 0 1 N N S 15.523 17.148 34.725 -0.642 0.119  -1.853 C10    DM3 13 
DM3 O10    O10  O 0 1 N N N 15.669 16.622 33.324 0.647  -0.400 -2.181 O10    DM3 14 
DM3 C11    C11  C 0 1 N N N 16.792 17.814 35.233 -1.688 -0.519 -2.764 C11    DM3 15 
DM3 C12    C12  C 0 1 N N S 17.075 19.194 34.766 -3.079 -0.118 -2.257 C12    DM3 16 
DM3 O12    O12  O 0 1 N N N 17.326 19.016 33.273 -4.070 -0.511 -3.208 O12    DM3 17 
DM3 C13    C13  C 0 1 N N N 18.423 19.836 35.155 -3.135 1.373  -2.051 C13    DM3 18 
DM3 O13    O13  O 0 1 N N N 18.298 20.856 36.045 -2.914 1.841  -0.960 O13    DM3 19 
DM3 C14    C14  C 0 1 N N N 19.687 19.455 34.442 -3.467 2.281  -3.208 C14    DM3 20 
DM3 C15    C15  C 0 1 N N N 15.960 20.185 34.958 -3.329 -0.830 -0.929 C15    DM3 21 
DM3 C16    C16  C 0 1 Y N N 14.649 19.518 34.659 -2.179 -0.607 0.018  C16    DM3 22 
DM3 C17    C17  C 0 1 Y N N 13.571 20.381 34.452 -2.404 -0.860 1.369  C17    DM3 23 
DM3 C18    C18  C 0 1 Y N N 12.340 19.745 34.167 -1.392 -0.683 2.300  C18    DM3 24 
DM3 C19    C19  C 0 1 N N N 11.275 20.644 33.981 -1.627 -0.947 3.736  C19    DM3 25 
DM3 O19    O19  O 0 1 N N N 11.439 21.952 34.014 -2.617 -1.553 4.096  O19    DM3 26 
DM3 C20    C20  C 0 1 Y N N 9.997  20.141 33.720 -0.641 -0.465 4.727  C20    DM3 27 
DM3 C21    C21  C 0 1 N N N 6.809  16.663 32.939 3.489  1.247  5.999  C21    DM3 28 
DM3 "C1'"  C1*  C 0 1 N N R 16.091 15.299 33.003 1.386  0.669  -2.773 "C1'"  DM3 29 
DM3 "C2'"  C2*  C 0 1 N N N 15.820 14.997 31.529 2.863  0.278  -2.865 "C2'"  DM3 30 
DM3 "C3'"  C3*  C 0 1 N N S 16.874 15.676 30.696 2.990  -0.996 -3.706 "C3'"  DM3 31 
DM3 "N3'"  N3*  N 0 1 N N N 16.658 15.042 29.333 4.410  -1.299 -3.930 "N3'"  DM3 32 
DM3 "C4'"  C4*  C 0 1 N N S 18.372 15.415 31.105 2.290  -0.769 -5.050 "C4'"  DM3 33 
DM3 "O4'"  O4*  O 0 1 N N N 18.616 14.002 30.939 2.995  0.225  -5.794 "O4'"  DM3 34 
DM3 "C5'"  C5*  C 0 1 N N S 18.532 15.801 32.566 0.856  -0.299 -4.793 "C5'"  DM3 35 
DM3 "O5'"  O5*  O 0 1 N N N 17.478 15.017 33.332 0.875  0.933  -4.078 "O5'"  DM3 36 
DM3 "C6'"  C6*  C 0 1 N N N 19.918 15.575 33.133 0.138  -0.100 -6.129 "C6'"  DM3 37 
DM3 H1     H1   H 0 1 N N N 9.247  22.173 33.601 -1.924 -0.772 6.417  H1     DM3 38 
DM3 H2     H2   H 0 1 N N N 6.846  21.333 33.089 -0.268 0.037  8.049  H2     DM3 39 
DM3 H3     H3   H 0 1 N N N 6.366  18.931 32.979 1.939  0.798  7.307  H3     DM3 40 
DM3 HO8    HO8  H 0 1 N N N 13.879 15.612 34.313 1.282  1.390  0.080  HO8    DM3 41 
DM3 H10    H10  H 0 1 N N N 15.308 16.342 35.465 -0.644 1.198  -2.006 H10    DM3 42 
DM3 H111   1H11 H 0 0 N N N 16.798 17.793 36.347 -1.586 -1.604 -2.736 H111   DM3 43 
DM3 H112   2H11 H 0 0 N N N 17.667 17.161 35.006 -1.553 -0.163 -3.785 H112   DM3 44 
DM3 HO12   2HO1 H 0 0 N N N 17.507 19.899 32.974 -4.927 -0.256 -2.840 HO12   DM3 45 
DM3 H141   1H14 H 0 0 N N N 20.661 19.918 34.723 -3.460 3.317  -2.870 H141   DM3 46 
DM3 H142   2H14 H 0 0 N N N 19.799 18.347 34.500 -2.725 2.151  -3.996 H142   DM3 47 
DM3 H143   3H14 H 0 0 N N N 19.530 19.609 33.349 -4.455 2.031  -3.594 H143   DM3 48 
DM3 H151   1H15 H 0 0 N N N 15.976 20.649 35.971 -3.444 -1.899 -1.111 H151   DM3 49 
DM3 H152   2H15 H 0 0 N N N 16.109 21.112 34.356 -4.244 -0.443 -0.481 H152   DM3 50 
DM3 H17    H17  H 0 1 N N N 13.682 21.476 34.509 -3.377 -1.197 1.695  H17    DM3 51 
DM3 H211   1H21 H 0 0 N N N 6.607  15.568 32.872 4.484  1.597  5.721  H211   DM3 52 
DM3 H212   2H21 H 0 0 N N N 6.106  17.141 33.660 2.947  2.052  6.496  H212   DM3 53 
DM3 H213   3H21 H 0 0 N N N 6.494  17.170 31.997 3.578  0.397  6.675  H213   DM3 54 
DM3 "H1'"  H1*  H 0 1 N N N 15.484 14.622 33.649 1.286  1.563  -2.157 "H1'"  DM3 55 
DM3 "H2'1" 1H2* H 0 0 N N N 15.752 13.903 31.322 3.424  1.084  -3.337 "H2'1" DM3 56 
DM3 "H2'2" 2H2* H 0 0 N N N 14.785 15.276 31.219 3.255  0.096  -1.864 "H2'2" DM3 57 
DM3 "H3'"  H3*  H 0 1 N N N 16.757 16.781 30.786 2.517  -1.828 -3.183 "H3'"  DM3 58 
DM3 "HN'1" 1HN* H 0 0 N N N 17.372 15.502 28.768 4.826  -1.427 -3.021 "HN'1" DM3 59 
DM3 "HN'2" 2HN* H 0 0 N N N 15.707 15.113 28.969 4.445  -2.194 -4.394 "HN'2" DM3 60 
DM3 "H4'"  H4*  H 0 1 N N N 19.086 16.005 30.485 2.271  -1.702 -5.614 "H4'"  DM3 61 
DM3 "HO4'" *HO4 H 0 0 N N N 19.519 13.844 31.185 2.522  0.337  -6.630 "HO4'" DM3 62 
DM3 "H5'"  H5*  H 0 1 N N N 18.392 16.902 32.665 0.328  -1.050 -4.206 "H5'"  DM3 63 
DM3 "H6'1" 1H6* H 0 0 N N N 20.035 15.858 34.205 -0.882 0.234  -5.947 "H6'1" DM3 64 
DM3 "H6'2" 2H6* H 0 0 N N N 20.232 14.516 32.976 0.667  0.649  -6.718 "H6'2" DM3 65 
DM3 "H6'3" 3H6* H 0 0 N N N 20.680 16.097 32.509 0.119  -1.043 -6.675 "H6'3" DM3 66 
# 
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 
DM3 C1    C2     DOUB Y N 1  
DM3 C1    C20    SING Y N 2  
DM3 C1    H1     SING N N 3  
DM3 C2    C3     SING Y N 4  
DM3 C2    H2     SING N N 5  
DM3 C3    C4     DOUB Y N 6  
DM3 C3    H3     SING N N 7  
DM3 C4    O4     SING N N 8  
DM3 C4    C5     SING Y N 9  
DM3 O4    C21    SING N N 10 
DM3 C5    C6     SING N N 11 
DM3 C5    C20    DOUB Y N 12 
DM3 C6    O6     DOUB N N 13 
DM3 C6    C7     SING N N 14 
DM3 C7    C8     DOUB Y N 15 
DM3 C7    C18    SING Y N 16 
DM3 C8    O8     SING N N 17 
DM3 C8    C9     SING Y N 18 
DM3 O8    HO8    SING N N 19 
DM3 C9    C10    SING N N 20 
DM3 C9    C16    DOUB Y N 21 
DM3 C10   O10    SING N N 22 
DM3 C10   C11    SING N N 23 
DM3 C10   H10    SING N N 24 
DM3 O10   "C1'"  SING N N 25 
DM3 C11   C12    SING N N 26 
DM3 C11   H111   SING N N 27 
DM3 C11   H112   SING N N 28 
DM3 C12   O12    SING N N 29 
DM3 C12   C13    SING N N 30 
DM3 C12   C15    SING N N 31 
DM3 O12   HO12   SING N N 32 
DM3 C13   O13    DOUB N N 33 
DM3 C13   C14    SING N N 34 
DM3 C14   H141   SING N N 35 
DM3 C14   H142   SING N N 36 
DM3 C14   H143   SING N N 37 
DM3 C15   C16    SING N N 38 
DM3 C15   H151   SING N N 39 
DM3 C15   H152   SING N N 40 
DM3 C16   C17    SING Y N 41 
DM3 C17   C18    DOUB Y N 42 
DM3 C17   H17    SING N N 43 
DM3 C18   C19    SING N N 44 
DM3 C19   O19    DOUB N N 45 
DM3 C19   C20    SING N N 46 
DM3 C21   H211   SING N N 47 
DM3 C21   H212   SING N N 48 
DM3 C21   H213   SING N N 49 
DM3 "C1'" "C2'"  SING N N 50 
DM3 "C1'" "O5'"  SING N N 51 
DM3 "C1'" "H1'"  SING N N 52 
DM3 "C2'" "C3'"  SING N N 53 
DM3 "C2'" "H2'1" SING N N 54 
DM3 "C2'" "H2'2" SING N N 55 
DM3 "C3'" "N3'"  SING N N 56 
DM3 "C3'" "C4'"  SING N N 57 
DM3 "C3'" "H3'"  SING N N 58 
DM3 "N3'" "HN'1" SING N N 59 
DM3 "N3'" "HN'2" SING N N 60 
DM3 "C4'" "O4'"  SING N N 61 
DM3 "C4'" "C5'"  SING N N 62 
DM3 "C4'" "H4'"  SING N N 63 
DM3 "O4'" "HO4'" SING N N 64 
DM3 "C5'" "O5'"  SING N N 65 
DM3 "C5'" "C6'"  SING N N 66 
DM3 "C5'" "H5'"  SING N N 67 
DM3 "C6'" "H6'1" SING N N 68 
DM3 "C6'" "H6'2" SING N N 69 
DM3 "C6'" "H6'3" SING N N 70 
# 
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 
DM3 SMILES           ACDLabs              10.04 O=C2c1cc5c(c(O)c1C(=O)c3c2cccc3OC)C(OC4OC(C(O)C(N)C4)C)CC(O)(C(=O)C)C5 
DM3 InChI            InChI                1.02b 
InChI=1/C27H29NO9/c1-11-23(30)16(28)8-19(36-11)37-18-10-27(34,12(2)29)9-13-7-15-22(25(32)20(13)18)26(33)21-14(24(15)31)5-4-6-17(21)35-3/h4-7,11,16,18-19,23,30,32,34H,8-10,28H2,1-3H3/t11-,16-,18-,19-,23+,27-/m0/s1 
DM3 InChIKey         InChI                1.02b ZCLQMQOBRBUQOR-GRRPPOEGBA 
DM3 SMILES_CANONICAL CACTVS               3.341 COc1cccc2C(=O)c3cc4C[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 
DM3 SMILES           CACTVS               3.341 COc1cccc2C(=O)c3cc4C[C](O)(C[CH](O[CH]5C[CH](N)[CH](O)[CH](C)O5)c4c(O)c3C(=O)c12)C(C)=O 
DM3 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)OC)O)(C(=O)C)O)N)O 
DM3 SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3)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 
DM3 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3S)-3-acetyl-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside" 
DM3 "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-dihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione      
# 
