data_DXA
# 
_chem_comp.id                                    DXA 
_chem_comp.name                                  1,2-HYDRO-1-OXY-3,4-HYDRO-3-(1-METHOXY-2-OXY-3,4-DIHYDROXYPENTYL)-8,9-DIHYDROXY-7-(SEC-BUTYL)-ANTHRACENE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H30 O7" 
_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                        430.491 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DXA 
_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        1CP8 
_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 
DXA C1    C1    C 0 1 N N N 8.609  -2.559 -4.732 -2.105 -0.572 -0.621 C1    DXA 1  
DXA O1    O1    O 0 1 N N N 7.781  -3.114 -4.072 -3.199 -0.934 -0.239 O1    DXA 2  
DXA C9A   C9A   C 0 1 Y N N 8.362  -1.212 -5.293 -1.075 -0.134 0.329  C9A   DXA 3  
DXA C2    C2    C 0 1 N N N 9.962  -3.247 -5.023 -1.756 -0.557 -2.095 C2    DXA 4  
DXA C3    C3    C 0 1 N N R 10.441 -2.904 -6.449 -1.003 0.749  -2.375 C3    DXA 5  
DXA C4    C4    C 0 1 N N N 10.572 -1.377 -6.636 0.314  0.749  -1.606 C4    DXA 6  
DXA C4A   C4A   C 0 1 Y N N 9.311  -0.630 -6.258 0.089  0.508  -0.137 C4A   DXA 7  
DXA C10   C10   C 0 1 Y N N 9.034  0.683  -6.822 1.038  0.923  0.743  C10   DXA 8  
DXA C5A   C5A   C 0 1 Y N N 7.847  1.392  -6.425 0.877  0.714  2.126  C5A   DXA 9  
DXA C5    C5    C 0 1 Y N N 7.598  2.677  -7.005 1.854  1.141  3.038  C5    DXA 10 
DXA C6    C6    C 0 1 Y N N 6.397  3.422  -6.632 1.683  0.924  4.373  C6    DXA 11 
DXA C7    C7    C 0 1 Y N N 5.457  2.863  -5.654 0.549  0.281  4.856  C7    DXA 12 
DXA C8    C8    C 0 1 Y N N 5.720  1.545  -5.095 -0.432 -0.156 3.993  C8    DXA 13 
DXA O8    O8    O 0 1 N N N 4.770  0.949  -4.298 -1.534 -0.786 4.472  O8    DXA 14 
DXA C8A   C8A   C 0 1 Y N N 6.917  0.819  -5.475 -0.283 0.061  2.608  C8A   DXA 15 
DXA C9    C9    C 0 1 Y N N 7.167  -0.485 -4.905 -1.265 -0.362 1.695  C9    DXA 16 
DXA O9    O9    O 0 1 N N N 6.370  -0.972 -4.120 -2.384 -0.984 2.135  O9    DXA 17 
DXA CME   CME   C 0 1 N N N 11.137 -5.601 -7.774 -2.246 2.381  -4.670 CME   DXA 18 
DXA "C6'" "C6'" C 0 1 N N R 4.313  3.706  -5.121 0.394  0.056  6.338  "C6'" DXA 19 
DXA "C1'" "C1'" C 0 1 N N S 11.780 -3.585 -6.741 -0.720 0.864  -3.874 "C1'" DXA 20 
DXA "O1'" "O1'" O 0 1 N N N 11.647 -4.985 -6.612 -1.954 0.985  -4.584 "O1'" DXA 21 
DXA "C2'" "C2'" C 0 1 N N N 12.831 -3.090 -5.745 0.011  -0.366 -4.343 "C2'" DXA 22 
DXA "O2'" "O2'" O 0 1 N N N 12.895 -3.527 -4.636 -0.610 -1.323 -4.739 "O2'" DXA 23 
DXA "C3'" "C3'" C 0 1 N N S 13.797 -2.010 -6.235 1.517  -0.404 -4.317 "C3'" DXA 24 
DXA "O3'" "O3'" O 0 1 N N N 13.626 -0.845 -5.468 1.956  -1.748 -4.114 "O3'" DXA 25 
DXA "C4'" "C4'" C 0 1 N N R 15.239 -2.500 -6.104 2.063  0.114  -5.649 "C4'" DXA 26 
DXA "O4'" "O4'" O 0 1 N N N 16.100 -1.510 -6.605 1.584  -0.709 -6.714 "O4'" DXA 27 
DXA "C5'" "C5'" C 0 1 N N N 15.474 -3.796 -6.881 3.592  0.076  -5.623 "C5'" DXA 28 
DXA "C7'" "C7'" C 0 1 N N N 3.376  4.157  -6.245 0.397  1.404  7.062  "C7'" DXA 29 
DXA "C8'" "C8'" C 0 1 N N N 4.882  4.918  -4.372 1.554  -0.799 6.848  "C8'" DXA 30 
DXA "C9'" "C9'" C 0 1 N N N 3.781  5.884  -3.934 1.397  -1.028 8.353  "C9'" DXA 31 
DXA H21   1H2   H 0 1 N N N 10.693 -2.904 -4.288 -2.667 -0.594 -2.692 H21   DXA 32 
DXA H22   2H2   H 0 1 N N N 9.913  -4.348 -4.854 -1.120 -1.409 -2.334 H22   DXA 33 
DXA H3    H3    H 0 1 N N N 9.702  -3.274 -7.158 -1.611 1.595  -2.054 H3    DXA 34 
DXA H4A   H4A   H 0 1 N N N 11.395 -0.999 -6.029 0.805  1.713  -1.739 H4A   DXA 35 
DXA H4E   H4E   H 0 1 N N N 10.813 -1.151 -7.675 0.958  -0.035 -2.002 H4E   DXA 36 
DXA H10   H10   H 0 1 N N N 9.707  1.121  -7.548 1.925  1.419  0.377  H10   DXA 37 
DXA H5    H5    H 0 1 N N N 8.297  3.095  -7.709 2.742  1.643  2.682  H5    DXA 38 
DXA H6    H6    H 0 1 N N N 6.200  4.406  -7.088 2.441  1.257  5.066  H6    DXA 39 
DXA HO8   HO8   H 0 1 N N N 5.182  0.312  -3.756 -1.330 -1.731 4.489  HO8   DXA 40 
DXA HO9   HO9   H 0 1 N N N 5.587  -0.496 -3.866 -2.191 -1.931 2.148  HO9   DXA 41 
DXA H11   1H1   H 0 1 N N N 11.908 -5.653 -8.543 -3.222 2.520  -5.135 H11   DXA 42 
DXA H12   2H1   H 0 1 N N N 10.802 -6.614 -7.549 -2.256 2.812  -3.669 H12   DXA 43 
DXA H13   3H1   H 0 1 N N N 10.293 -5.035 -8.165 -1.483 2.876  -5.271 H13   DXA 44 
DXA "H6'" "H6'" H 0 1 N N N 3.744  3.098  -4.417 -0.548 -0.456 6.531  "H6'" DXA 45 
DXA "H1'" "H1'" H 0 1 N N N 12.118 -3.343 -7.750 -0.105 1.745  -4.061 "H1'" DXA 46 
DXA "H3'" "H3'" H 0 1 N N N 13.564 -1.769 -7.272 1.882  0.224  -3.505 "H3'" DXA 47 
DXA HO3   HO3   H 0 1 N N N 13.086 -0.258 -5.981 1.613  -2.269 -4.852 HO3   DXA 48 
DXA "H4'" "H4'" H 0 1 N N N 15.489 -2.646 -5.053 1.728  1.140  -5.804 "H4'" DXA 49 
DXA HO4   HO4   H 0 1 N N N 16.984 -1.816 -6.453 1.902  -1.605 -6.538 HO4   DXA 50 
DXA H51   1H5   H 0 1 N N N 14.828 -4.593 -6.513 3.981  0.446  -6.572 H51   DXA 51 
DXA H52   2H5   H 0 1 N N N 15.266 -3.656 -7.942 3.957  0.705  -4.811 H52   DXA 52 
DXA H53   3H5   H 0 1 N N N 16.508 -4.127 -6.781 3.927  -0.949 -5.468 H53   DXA 53 
DXA H71   1H7   H 0 1 N N N 2.432  4.521  -5.839 1.339  1.917  6.869  H71   DXA 54 
DXA H72   2H7   H 0 1 N N N 3.151  3.333  -6.921 -0.429 2.014  6.699  H72   DXA 55 
DXA H73   3H7   H 0 1 N N N 3.823  4.960  -6.828 0.285  1.241  8.134  H73   DXA 56 
DXA H81   1H8   H 0 1 N N N 5.592  5.444  -5.009 2.496  -0.286 6.656  H81   DXA 57 
DXA H82   2H8   H 0 1 N N N 5.438  4.578  -3.498 1.552  -1.759 6.333  H82   DXA 58 
DXA H91   1H9   H 0 1 N N N 3.124  5.420  -3.200 2.224  -1.638 8.716  H91   DXA 59 
DXA H92   2H9   H 0 1 N N N 3.173  6.193  -4.784 1.399  -0.068 8.869  H92   DXA 60 
DXA H93   3H9   H 0 1 N N N 4.209  6.781  -3.484 0.454  -1.541 8.545  H93   DXA 61 
# 
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 
DXA C1    O1    DOUB N N 1  
DXA C1    C9A   SING N N 2  
DXA C1    C2    SING N N 3  
DXA C9A   C4A   DOUB Y N 4  
DXA C9A   C9    SING Y N 5  
DXA C2    C3    SING N N 6  
DXA C2    H21   SING N N 7  
DXA C2    H22   SING N N 8  
DXA C3    C4    SING N N 9  
DXA C3    "C1'" SING N N 10 
DXA C3    H3    SING N N 11 
DXA C4    C4A   SING N N 12 
DXA C4    H4A   SING N N 13 
DXA C4    H4E   SING N N 14 
DXA C4A   C10   SING Y N 15 
DXA C10   C5A   DOUB Y N 16 
DXA C10   H10   SING N N 17 
DXA C5A   C5    SING Y N 18 
DXA C5A   C8A   SING Y N 19 
DXA C5    C6    DOUB Y N 20 
DXA C5    H5    SING N N 21 
DXA C6    C7    SING Y N 22 
DXA C6    H6    SING N N 23 
DXA C7    C8    DOUB Y N 24 
DXA C7    "C6'" SING N N 25 
DXA C8    O8    SING N N 26 
DXA C8    C8A   SING Y N 27 
DXA O8    HO8   SING N N 28 
DXA C8A   C9    DOUB Y N 29 
DXA C9    O9    SING N N 30 
DXA O9    HO9   SING N N 31 
DXA CME   "O1'" SING N N 32 
DXA CME   H11   SING N N 33 
DXA CME   H12   SING N N 34 
DXA CME   H13   SING N N 35 
DXA "C6'" "C7'" SING N N 36 
DXA "C6'" "C8'" SING N N 37 
DXA "C6'" "H6'" SING N N 38 
DXA "C1'" "O1'" SING N N 39 
DXA "C1'" "C2'" SING N N 40 
DXA "C1'" "H1'" SING N N 41 
DXA "C2'" "O2'" DOUB N N 42 
DXA "C2'" "C3'" SING N N 43 
DXA "C3'" "O3'" SING N N 44 
DXA "C3'" "C4'" SING N N 45 
DXA "C3'" "H3'" SING N N 46 
DXA "O3'" HO3   SING N N 47 
DXA "C4'" "O4'" SING N N 48 
DXA "C4'" "C5'" SING N N 49 
DXA "C4'" "H4'" SING N N 50 
DXA "O4'" HO4   SING N N 51 
DXA "C5'" H51   SING N N 52 
DXA "C5'" H52   SING N N 53 
DXA "C5'" H53   SING N N 54 
DXA "C7'" H71   SING N N 55 
DXA "C7'" H72   SING N N 56 
DXA "C7'" H73   SING N N 57 
DXA "C8'" "C9'" SING N N 58 
DXA "C8'" H81   SING N N 59 
DXA "C8'" H82   SING N N 60 
DXA "C9'" H91   SING N N 61 
DXA "C9'" H92   SING N N 62 
DXA "C9'" H93   SING N N 63 
# 
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 
DXA SMILES           ACDLabs              10.04 O=C(C(O)C(O)C)C(OC)C3CC(=O)c2c(cc1ccc(c(O)c1c2O)C(C)CC)C3                                                                                                                              
DXA InChI            InChI                1.02b InChI=1/C24H30O7/c1-5-11(2)16-7-6-13-8-14-9-15(24(31-4)23(30)20(27)12(3)25)10-17(26)18(14)22(29)19(13)21(16)28/h6-8,11-12,15,20,24-25,27-29H,5,9-10H2,1-4H3/t11-,12-,15-,20+,24+/m1/s1 
DXA InChIKey         InChI                1.02b XGORHSPGULYMCV-HHYQQTLHBH                                                                                                                                                              
DXA SMILES_CANONICAL CACTVS               3.341 CC[C@@H](C)c1ccc2cc3C[C@H](CC(=O)c3c(O)c2c1O)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O                                                                                                         
DXA SMILES           CACTVS               3.341 CC[CH](C)c1ccc2cc3C[CH](CC(=O)c3c(O)c2c1O)[CH](OC)C(=O)[CH](O)[CH](C)O                                                                                                                 
DXA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H](C)c1ccc2cc3c(c(c2c1O)O)C(=O)C[C@@H](C3)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC                                                                                                      
DXA SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)c1ccc2cc3c(c(c2c1O)O)C(=O)CC(C3)C(C(=O)C(C(C)O)O)OC                                                                                                                              
# 
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 
DXA "SYSTEMATIC NAME" ACDLabs              10.04 (1S)-5-deoxy-1-C-{(2R)-5,10-dihydroxy-6-[(1R)-1-methylpropyl]-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl}-1-O-methyl-D-xylulose 
DXA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3R)-7-[(2R)-butan-2-yl]-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxo-pentyl]-8,9-dihydroxy-3,4-dihydro-2H-anthracen-1-one   
# 
