data_MAR
# 
_chem_comp.id                                    MAR 
_chem_comp.name                                  "4'-EPI-4'-(2-DEOXYFUCOSE)DAUNOMYCIN" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C33 H39 N O13" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MAR70;DAUNOMYCIN 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                        657.662 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MAR 
_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        1D35 
_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 
MAR C1     C1   C 0 1 Y N N 15.258 18.419 5.102  1.206  0.347  -7.667 C1     MAR 1  
MAR C2     C2   C 0 1 Y N N 16.402 19.206 5.113  2.422  -0.106 -8.154 C2     MAR 2  
MAR C3     C3   C 0 1 Y N N 17.727 18.632 5.102  3.410  -0.530 -7.290 C3     MAR 3  
MAR C4     C4   C 0 1 Y N N 17.859 17.170 5.033  3.199  -0.508 -5.913 C4     MAR 4  
MAR O4     O4   O 0 1 N N N 19.012 16.537 5.012  4.173  -0.925 -5.068 O4     MAR 5  
MAR C5     C5   C 0 1 Y N N 16.630 16.450 5.023  1.977  -0.058 -5.409 C5     MAR 6  
MAR C6     C6   C 0 1 N N N 16.715 14.951 4.938  1.732  -0.020 -3.955 C6     MAR 7  
MAR O6     O6   O 0 1 N N N 17.758 14.285 4.890  2.653  -0.146 -3.171 O6     MAR 8  
MAR C7     C7   C 0 1 Y N N 15.429 14.198 4.932  0.354  0.166  -3.463 C7     MAR 9  
MAR C8     C8   C 0 1 Y N N 15.480 12.814 4.895  0.032  -0.080 -2.131 C8     MAR 10 
MAR O8     O8   O 0 1 N N N 16.602 12.139 4.895  0.994  -0.496 -1.271 O8     MAR 11 
MAR C9     C9   C 0 1 Y N N 14.243 12.117 4.864  -1.280 0.096  -1.673 C9     MAR 12 
MAR C10    C10  C 0 1 N N S 14.316 10.548 4.890  -1.552 -0.198 -0.221 C10    MAR 13 
MAR O10    O10  O 0 1 N N N 14.943 10.376 6.236  -0.487 0.326  0.572  O10    MAR 14 
MAR C11    C11  C 0 1 N N N 13.006 9.876  4.773  -2.869 0.435  0.220  C11    MAR 15 
MAR C12    C12  C 0 1 N N S 11.810 10.587 5.351  -3.960 0.029  -0.777 C12    MAR 16 
MAR O12    O12  O 0 1 N N N 11.920 10.666 6.829  -5.240 0.420  -0.277 O12    MAR 17 
MAR C13    C13  C 0 1 N N N 10.517 9.834  5.139  -3.929 -1.462 -0.985 C13    MAR 18 
MAR O13    O13  O 0 1 N N N 9.879  10.025 4.101  -3.307 -1.931 -1.908 O13    MAR 19 
MAR C14    C14  C 0 1 N N N 10.028 8.745  6.103  -4.675 -2.370 -0.041 C14    MAR 20 
MAR C15    C15  C 0 1 N N N 11.675 12.069 4.858  -3.686 0.739  -2.101 C15    MAR 21 
MAR C16    C16  C 0 1 Y N N 12.986 12.713 4.879  -2.259 0.520  -2.536 C16    MAR 22 
MAR C17    C17  C 0 1 Y N N 12.986 14.119 4.922  -1.951 0.773  -3.880 C17    MAR 23 
MAR O17    O17  O 0 1 N N N 11.760 14.777 4.932  -2.924 1.191  -4.727 O17    MAR 24 
MAR C18    C18  C 0 1 Y N N 14.116 14.906 4.948  -0.652 0.598  -4.351 C18    MAR 25 
MAR C19    C19  C 0 1 N N N 14.108 16.357 5.001  -0.317 0.858  -5.763 C19    MAR 26 
MAR O19    O19  O 0 1 N N N 13.067 17.032 5.007  -1.094 1.461  -6.479 O19    MAR 27 
MAR C20    C20  C 0 1 Y N N 15.396 17.027 5.023  0.974  0.377  -6.298 C20    MAR 28 
MAR C21    C21  C 0 1 N N N 20.277 17.336 5.272  5.281  -1.323 -5.878 C21    MAR 29 
MAR "C1'"  C1*  C 0 1 N N R 15.823 9.336  6.485  -0.091 -0.711 1.471  "C1'"  MAR 30 
MAR "C2'"  C2*  C 0 1 N N N 16.855 9.679  7.523  1.245  -0.342 2.118  "C2'"  MAR 31 
MAR "C3'"  C3*  C 0 1 N N S 16.200 9.842  8.927  1.089  0.988  2.863  "C3'"  MAR 32 
MAR "N3'"  N3*  N 0 1 N N N 17.330 10.044 9.944  2.318  1.279  3.613  "N3'"  MAR 33 
MAR "C4'"  C4*  C 0 1 N N S 15.407 8.577  9.261  -0.093 0.873  3.830  "C4'"  MAR 34 
MAR "O4'"  O4*  O 0 1 N N N 16.374 7.500  9.473  0.214  -0.078 4.851  "O4'"  MAR 35 
MAR "C5'"  C5*  C 0 1 N N S 14.341 8.329  8.217  -1.329 0.412  3.054  "C5'"  MAR 36 
MAR "O5'"  O5*  O 0 1 N N N 15.047 8.132  6.882  -1.087 -0.869 2.480  "O5'"  MAR 37 
MAR "C6'"  C6*  C 0 1 N N N 13.531 7.024  8.366  -2.524 0.325  4.006  "C6'"  MAR 38 
MAR CB1    CB1  C 0 1 N N S 15.958 6.462  10.358 -0.312 0.442  6.073  CB1    MAR 39 
MAR CB2    CB2  C 0 1 N N N 16.580 5.152  10.013 -0.355 -0.669 7.124  CB2    MAR 40 
MAR CB3    CB3  C 0 1 N N S 18.101 5.062  10.342 1.062  -1.213 7.334  CB3    MAR 41 
MAR OB3    OB3  O 0 1 N N N 18.365 3.597  10.188 1.061  -2.148 8.415  OB3    MAR 42 
MAR CB4    CB4  C 0 1 N N R 18.354 5.531  11.777 1.993  -0.041 7.662  CB4    MAR 43 
MAR OB4    OB4  O 0 1 N N N 19.813 5.427  11.995 3.344  -0.504 7.717  OB4    MAR 44 
MAR CB5    CB5  C 0 1 N N S 17.806 6.926  11.984 1.859  1.023  6.571  CB5    MAR 45 
MAR OB5    OB5  O 0 1 N N N 16.324 6.864  11.735 0.519  1.506  6.533  OB5    MAR 46 
MAR CB6    CB6  C 0 1 N N N 17.904 7.435  13.446 2.809  2.183  6.874  CB6    MAR 47 
MAR H1     H1   H 0 1 N N N 14.261 18.889 5.154  0.439  0.677  -8.352 H1     MAR 48 
MAR H2     H2   H 0 1 N N N 16.256 20.299 5.130  2.597  -0.129 -9.219 H2     MAR 49 
MAR H3     H3   H 0 1 N N N 18.611 19.290 5.145  4.353  -0.881 -7.683 H3     MAR 50 
MAR HO8    HO8  H 0 1 N N N 16.637 11.190 4.869  1.056  -1.456 -1.363 HO8    MAR 51 
MAR H10    H10  H 0 1 N N N 14.863 10.091 4.032  -1.609 -1.278 -0.078 H10    MAR 52 
MAR H111   1H11 H 0 0 N N N 12.809 9.632  3.702  -2.768 1.521  0.232  H111   MAR 53 
MAR H112   2H11 H 0 0 N N N 13.074 8.852  5.210  -3.132 0.080  1.216  H112   MAR 54 
MAR HO12   2HO1 H 0 0 N N N 11.165 11.114 7.193  -5.891 0.162  -0.944 HO12   MAR 55 
MAR H141   1H14 H 0 0 N N N 9.074  8.189  5.946  -4.537 -3.406 -0.349 H141   MAR 56 
MAR H142   2H14 H 0 0 N N N 10.843 7.991  6.200  -4.290 -2.237 0.969  H142   MAR 57 
MAR H143   3H14 H 0 0 N N N 9.994  9.190  7.124  -5.736 -2.123 -0.062 H143   MAR 58 
MAR H151   1H15 H 0 0 N N N 11.188 12.136 3.856  -3.864 1.807  -1.980 H151   MAR 59 
MAR H152   2H15 H 0 0 N N N 10.916 12.639 5.443  -4.358 0.348  -2.865 H152   MAR 60 
MAR HO17   7HO1 H 0 0 N N N 11.760 15.726 4.961  -3.319 0.397  -5.112 HO17   MAR 61 
MAR H211   1H21 H 0 0 N N N 21.254 16.799 5.254  6.093  -1.668 -5.239 H211   MAR 62 
MAR H212   2H21 H 0 0 N N N 20.319 18.192 4.558  4.974  -2.130 -6.543 H212   MAR 63 
MAR H213   3H21 H 0 0 N N N 20.174 17.872 6.244  5.621  -0.474 -6.471 H213   MAR 64 
MAR "H1'"  H1*  H 0 1 N N N 16.390 9.132  5.547  0.017  -1.646 0.921  "H1'"  MAR 65 
MAR "H2'1" 1H2* H 0 0 N N N 17.685 8.934  7.539  1.537  -1.122 2.822  "H2'1" MAR 66 
MAR "H2'2" 2H2* H 0 0 N N N 17.443 10.581 7.236  2.008  -0.241 1.346  "H2'2" MAR 67 
MAR "H3'"  H3*  H 0 1 N N N 15.504 10.713 8.948  0.900  1.787  2.147  "H3'"  MAR 68 
MAR "HN'1" 1HN* H 0 0 N N N 16.901 10.150 10.863 3.065  1.332  2.937  "HN'1" MAR 69 
MAR "HN'2" 2HN* H 0 0 N N N 17.948 10.818 9.702  2.209  2.205  3.999  "HN'2" MAR 70 
MAR "H4'"  H4*  H 0 1 N N N 14.820 8.667  10.204 -0.289 1.844  4.284  "H4'"  MAR 71 
MAR "H5'"  H5*  H 0 1 N N N 13.650 9.199  8.313  -1.548 1.128  2.262  "H5'"  MAR 72 
MAR "H6'1" 1H6* H 0 0 N N N 12.745 6.841  7.596  -3.422 0.078  3.440  "H6'1" MAR 73 
MAR "H6'2" 2H6* H 0 0 N N N 14.225 6.152  8.410  -2.340 -0.448 4.751  "H6'2" MAR 74 
MAR "H6'3" 3H6* H 0 0 N N N 13.079 6.974  9.384  -2.661 1.284  4.505  "H6'3" MAR 75 
MAR HB1    HB1  H 0 1 N N N 14.855 6.322  10.267 -1.320 0.818  5.902  HB1    MAR 76 
MAR HB21   1HB2 H 0 0 N N N 16.025 4.316  10.499 -0.735 -0.269 8.063  HB21   MAR 77 
MAR HB22   2HB2 H 0 0 N N N 16.396 4.902  8.941  -1.006 -1.472 6.778  HB22   MAR 78 
MAR HB3    HB3  H 0 1 N N N 18.755 5.696  9.699  1.402  -1.707 6.424  HB3    MAR 79 
MAR HOB3   3HOB H 0 0 N N N 19.292 3.542  10.388 0.455  -2.859 8.169  HOB3   MAR 80 
MAR HB4    HB4  H 0 1 N N N 17.824 4.902  12.530 1.715  0.386  8.626  HB4    MAR 81 
MAR HOB4   4HOB H 0 0 N N N 19.970 5.718  12.885 3.894  0.262  7.926  HOB4   MAR 82 
MAR HB5    HB5  H 0 1 N N N 18.394 7.593  11.311 2.115  0.587  5.606  HB5    MAR 83 
MAR HB61   1HB6 H 0 0 N N N 17.500 8.463  13.598 2.714  2.942  6.097  HB61   MAR 84 
MAR HB62   2HB6 H 0 0 N N N 17.415 6.715  14.143 2.555  2.619  7.840  HB62   MAR 85 
MAR HB63   3HB6 H 0 0 N N N 18.954 7.369  13.812 3.835  1.816  6.899  HB63   MAR 86 
# 
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 
MAR C1    C2     DOUB Y N 1  
MAR C1    C20    SING Y N 2  
MAR C1    H1     SING N N 3  
MAR C2    C3     SING Y N 4  
MAR C2    H2     SING N N 5  
MAR C3    C4     DOUB Y N 6  
MAR C3    H3     SING N N 7  
MAR C4    O4     SING N N 8  
MAR C4    C5     SING Y N 9  
MAR O4    C21    SING N N 10 
MAR C5    C6     SING N N 11 
MAR C5    C20    DOUB Y N 12 
MAR C6    O6     DOUB N N 13 
MAR C6    C7     SING N N 14 
MAR C7    C8     DOUB Y N 15 
MAR C7    C18    SING Y N 16 
MAR C8    O8     SING N N 17 
MAR C8    C9     SING Y N 18 
MAR O8    HO8    SING N N 19 
MAR C9    C10    SING N N 20 
MAR C9    C16    DOUB Y N 21 
MAR C10   O10    SING N N 22 
MAR C10   C11    SING N N 23 
MAR C10   H10    SING N N 24 
MAR O10   "C1'"  SING N N 25 
MAR C11   C12    SING N N 26 
MAR C11   H111   SING N N 27 
MAR C11   H112   SING N N 28 
MAR C12   O12    SING N N 29 
MAR C12   C13    SING N N 30 
MAR C12   C15    SING N N 31 
MAR O12   HO12   SING N N 32 
MAR C13   O13    DOUB N N 33 
MAR C13   C14    SING N N 34 
MAR C14   H141   SING N N 35 
MAR C14   H142   SING N N 36 
MAR C14   H143   SING N N 37 
MAR C15   C16    SING N N 38 
MAR C15   H151   SING N N 39 
MAR C15   H152   SING N N 40 
MAR C16   C17    SING Y N 41 
MAR C17   O17    SING N N 42 
MAR C17   C18    DOUB Y N 43 
MAR O17   HO17   SING N N 44 
MAR C18   C19    SING N N 45 
MAR C19   O19    DOUB N N 46 
MAR C19   C20    SING N N 47 
MAR C21   H211   SING N N 48 
MAR C21   H212   SING N N 49 
MAR C21   H213   SING N N 50 
MAR "C1'" "C2'"  SING N N 51 
MAR "C1'" "O5'"  SING N N 52 
MAR "C1'" "H1'"  SING N N 53 
MAR "C2'" "C3'"  SING N N 54 
MAR "C2'" "H2'1" SING N N 55 
MAR "C2'" "H2'2" SING N N 56 
MAR "C3'" "N3'"  SING N N 57 
MAR "C3'" "C4'"  SING N N 58 
MAR "C3'" "H3'"  SING N N 59 
MAR "N3'" "HN'1" SING N N 60 
MAR "N3'" "HN'2" SING N N 61 
MAR "C4'" "O4'"  SING N N 62 
MAR "C4'" "C5'"  SING N N 63 
MAR "C4'" "H4'"  SING N N 64 
MAR "O4'" CB1    SING N N 65 
MAR "C5'" "O5'"  SING N N 66 
MAR "C5'" "C6'"  SING N N 67 
MAR "C5'" "H5'"  SING N N 68 
MAR "C6'" "H6'1" SING N N 69 
MAR "C6'" "H6'2" SING N N 70 
MAR "C6'" "H6'3" SING N N 71 
MAR CB1   CB2    SING N N 72 
MAR CB1   OB5    SING N N 73 
MAR CB1   HB1    SING N N 74 
MAR CB2   CB3    SING N N 75 
MAR CB2   HB21   SING N N 76 
MAR CB2   HB22   SING N N 77 
MAR CB3   OB3    SING N N 78 
MAR CB3   CB4    SING N N 79 
MAR CB3   HB3    SING N N 80 
MAR OB3   HOB3   SING N N 81 
MAR CB4   OB4    SING N N 82 
MAR CB4   CB5    SING N N 83 
MAR CB4   HB4    SING N N 84 
MAR OB4   HOB4   SING N N 85 
MAR CB5   OB5    SING N N 86 
MAR CB5   CB6    SING N N 87 
MAR CB5   HB5    SING N N 88 
MAR CB6   HB61   SING N N 89 
MAR CB6   HB62   SING N N 90 
MAR CB6   HB63   SING N N 91 
# 
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 
MAR SMILES           ACDLabs              10.04 O=C2c1c(O)c6c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)C)CC6OC5OC(C(OC4OC(C(O)C(O)C4)C)C(N)C5)C 
MAR InChI            InChI                1.02b 
;InChI=1/C33H39NO13/c1-12-27(37)18(36)9-22(44-12)47-32-13(2)45-21(8-17(32)34)46-20-11-33(42,14(3)35)10-16-24(20)31(41)26-25(29(16)39)28(38)15-6-5-7-19(43-4)23(15)30(26)40/h5-7,12-13,17-18,20-22,27,32,36-37,39,41-42H,8-11,34H2,1-4H3/t12-,13-,17-,18-,20-,21-,22-,27-,32+,33-/m0/s1
;
MAR InChIKey         InChI                1.02b QTGKDZKONUUXOU-NIGIIATCBD 
MAR 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]6C[C@H](O)[C@@H](O)[C@H](C)O6)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O 
MAR SMILES           CACTVS               3.341 COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH](N)[CH](O[CH]6C[CH](O)[CH](O)[CH](C)O6)[CH](C)O5)c4c(O)c3C(=O)c12)C(C)=O 
MAR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@@H]2[C@@H](O[C@H](C[C@@H]2N)O[C@H]3C[C@@](Cc4c3c(c5c(c4O)C(=O)c6cccc(c6C5=O)OC)O)(C(=O)C)O)C)O)O 
MAR SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(CC(O1)OC2C(OC(CC2N)OC3CC(Cc4c3c(c5c(c4O)C(=O)c6cccc(c6C5=O)OC)O)(C(=O)C)O)C)O)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 
MAR "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-2,3,6-trideoxy-4-O-(2,6-dideoxy-alpha-L-arabino-hexopyranosyl)-alpha-L-lyxo-hexopyranoside" 
MAR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyl-oxan-2-yl]oxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione         
# 
