data_CPH
# 
_chem_comp.id                                    CPH 
_chem_comp.name                                  1,8-DIHYDROXY-7-METHYL-3-(1,3,4-TRIHYDROXY-2-OXO-PENTYL)-3,10-DIHYDRO-2H-ANTHRACEN-9-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H24 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                        388.411 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CPH 
_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        1D83 
_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 
CPH C1    C1   C 0 1 N N N 7.516  -0.903 1.937  -0.324 -2.247 -0.428 C1    CPH 1  
CPH O1    O1   O 0 1 N N N 6.379  -0.993 2.364  0.573  -3.257 -0.295 O1    CPH 2  
CPH C9A   C9A  C 0 1 N N N 7.802  -0.117 0.793  -0.694 -1.419 0.743  C9A   CPH 3  
CPH C2    C2   C 0 1 N N N 8.584  -1.666 2.684  -0.878 -1.993 -1.610 C2    CPH 4  
CPH C3    C3   C 0 1 N N R 9.637  -2.189 1.669  -1.873 -0.871 -1.747 C3    CPH 5  
CPH C4    C4   C 0 1 N N N 10.058 -0.987 0.856  -2.727 -0.778 -0.484 C4    CPH 6  
CPH C4A   C4A  C 0 1 N N N 9.061  -0.157 0.221  -1.837 -0.715 0.738  C4A   CPH 7  
CPH C10   C10  C 0 1 N N N 9.478  0.543  -0.920 -2.275 0.121  1.902  C10   CPH 8  
CPH C5A   C5A  C 0 1 Y N N 8.566  1.339  -1.573 -1.163 0.472  2.844  C5A   CPH 9  
CPH C5    C5   C 0 1 Y N N 8.965  1.957  -2.787 -1.326 1.525  3.725  C5    CPH 10 
CPH C6    C6   C 0 1 Y N N 8.065  2.733  -3.476 -0.321 1.855  4.618  C6    CPH 11 
CPH C7    C7   C 0 1 Y N N 6.765  2.905  -2.926 0.860  1.141  4.646  C7    CPH 12 
CPH CC7   CC7  C 0 1 N N N 5.908  3.858  -3.696 1.942  1.509  5.627  CC7   CPH 13 
CPH C8    C8   C 0 1 Y N N 6.299  2.277  -1.689 1.046  0.083  3.768  C8    CPH 14 
CPH O8    O8   O 0 1 N N N 5.057  2.454  -1.054 2.204  -0.623 3.786  O8    CPH 15 
CPH C8A   C8A  C 0 1 Y N N 7.227  1.451  -1.013 0.032  -0.248 2.863  C8A   CPH 16 
CPH C9    C9   C 0 1 N N N 6.862  0.708  0.184  0.210  -1.363 1.912  C9    CPH 17 
CPH O9    O9   O 0 1 N N N 5.626  0.780  0.803  1.070  -2.205 2.083  O9    CPH 18 
CPH "C1'" C1*  C 0 1 N N S 10.907 -2.794 2.381  -1.127 0.447  -1.954 "C1'" CPH 19 
CPH "O1'" O1*  O 0 1 N N N 12.280 -2.393 2.163  -2.063 1.527  -1.971 "O1'" CPH 20 
CPH CME   CME  C 0 1 N N N 13.056 -1.596 3.114  -1.349 2.700  -1.576 CME   CPH 21 
CPH "C2'" C2*  C 0 1 N N N 10.796 -4.319 2.402  -0.385 0.404  -3.264 "C2'" CPH 22 
CPH "O2'" O2*  O 0 1 N N N 10.045 -4.850 3.198  -0.924 0.784  -4.276 "O2'" CPH 23 
CPH "C3'" C3*  C 0 1 N N S 11.611 -5.183 1.442  1.029  -0.112 -3.313 "C3'" CPH 24 
CPH "O3'" O3*  O 0 1 N N N 10.972 -6.448 1.301  1.276  -0.706 -4.589 "O3'" CPH 25 
CPH "C4'" C4*  C 0 1 N N R 11.720 -4.503 0.055  2.004  1.046  -3.092 "C4'" CPH 26 
CPH "O4'" O4*  O 0 1 N N N 10.781 -5.020 -0.880 1.819  2.025  -4.117 "O4'" CPH 27 
CPH "C5'" C5*  C 0 1 N N N 13.144 -4.792 -0.412 3.440  0.521  -3.142 "C5'" CPH 28 
CPH HO1   HO1  H 0 1 N N N 6.187  -1.519 3.130  0.669  -3.662 -1.168 HO1   CPH 29 
CPH H2    H2   H 0 1 N N N 8.593  -1.814 3.776  -0.616 -2.589 -2.471 H2    CPH 30 
CPH H3    H3   H 0 1 N N N 9.194  -3.004 1.051  -2.517 -1.061 -2.605 H3    CPH 31 
CPH H41   1H4  H 0 1 N N N 10.701 -0.338 1.494  -3.343 0.120  -0.530 H41   CPH 32 
CPH H42   2H4  H 0 1 N N N 10.782 -1.324 0.078  -3.372 -1.654 -0.418 H42   CPH 33 
CPH H101  1H10 H 0 0 N N N 10.373 1.155  -0.661 -2.714 1.044  1.523  H101  CPH 34 
CPH H102  2H10 H 0 0 N N N 9.914  -0.179 -1.648 -3.040 -0.423 2.455  H102  CPH 35 
CPH H5    H5   H 0 1 N N N 9.981  1.833  -3.197 -2.244 2.094  3.717  H5    CPH 36 
CPH H6    H6   H 0 1 N N N 8.372  3.197  -4.428 -0.463 2.681  5.300  H6    CPH 37 
CPH H71   1H7  H 0 1 N N N 4.888  3.992  -3.264 2.610  2.242  5.174  H71   CPH 38 
CPH H72   2H7  H 0 1 N N N 6.419  4.841  -3.811 1.491  1.934  6.524  H72   CPH 39 
CPH H73   3H7  H 0 1 N N N 5.845  3.553  -4.766 2.510  0.618  5.894  H73   CPH 40 
CPH HO8   HO8  H 0 1 N N N 4.754  2.046  -0.251 2.807  -0.188 3.168  HO8   CPH 41 
CPH "H1'" H1*  H 0 1 N N N 10.791 -2.243 3.343  -0.417 0.595  -1.139 "H1'" CPH 42 
CPH H11   H11  H 0 1 N N N 14.114 -1.287 2.946  -2.002 3.569  -1.660 H11   CPH 43 
CPH H12   H12  H 0 1 N N N 12.471 -0.668 3.319  -1.017 2.593  -0.543 H12   CPH 44 
CPH H13   H13  H 0 1 N N N 13.020 -2.127 4.093  -0.482 2.833  -2.224 H13   CPH 45 
CPH "H3'" H3*  H 0 1 N N N 12.638 -5.314 1.854  1.170  -0.858 -2.531 "H3'" CPH 46 
CPH HO3   HO3  H 0 1 N N N 11.479 -6.985 0.703  1.141  -0.013 -5.250 HO3   CPH 47 
CPH "H4'" H4*  H 0 1 N N N 11.497 -3.413 0.129  1.815  1.499  -2.119 "H4'" CPH 48 
CPH HO4   HO4  H 0 1 N N N 10.847 -4.602 -1.730 1.995  1.584  -4.960 HO4   CPH 49 
CPH H51   1H5  H 0 1 N N N 13.222 -4.302 -1.410 4.134  1.347  -2.985 H51   CPH 50 
CPH H52   2H5  H 0 1 N N N 13.930 -4.473 0.311  3.581  -0.224 -2.360 H52   CPH 51 
CPH H53   3H5  H 0 1 N N N 13.407 -5.875 -0.417 3.628  0.068  -4.115 H53   CPH 52 
# 
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 
CPH C1    O1    SING N N 1  
CPH C1    C9A   SING N N 2  
CPH C1    C2    DOUB N N 3  
CPH O1    HO1   SING N N 4  
CPH C9A   C4A   DOUB N N 5  
CPH C9A   C9    SING N N 6  
CPH C2    C3    SING N N 7  
CPH C2    H2    SING N N 8  
CPH C3    C4    SING N N 9  
CPH C3    "C1'" SING N N 10 
CPH C3    H3    SING N N 11 
CPH C4    C4A   SING N N 12 
CPH C4    H41   SING N N 13 
CPH C4    H42   SING N N 14 
CPH C4A   C10   SING N N 15 
CPH C10   C5A   SING N N 16 
CPH C10   H101  SING N N 17 
CPH C10   H102  SING N N 18 
CPH C5A   C5    DOUB Y N 19 
CPH C5A   C8A   SING Y N 20 
CPH C5    C6    SING Y N 21 
CPH C5    H5    SING N N 22 
CPH C6    C7    DOUB Y N 23 
CPH C6    H6    SING N N 24 
CPH C7    CC7   SING N N 25 
CPH C7    C8    SING Y N 26 
CPH CC7   H71   SING N N 27 
CPH CC7   H72   SING N N 28 
CPH CC7   H73   SING N N 29 
CPH C8    O8    SING N N 30 
CPH C8    C8A   DOUB Y N 31 
CPH O8    HO8   SING N N 32 
CPH C8A   C9    SING N N 33 
CPH C9    O9    DOUB N N 34 
CPH "C1'" "O1'" SING N N 35 
CPH "C1'" "C2'" SING N N 36 
CPH "C1'" "H1'" SING N N 37 
CPH "O1'" CME   SING N N 38 
CPH CME   H11   SING N N 39 
CPH CME   H12   SING N N 40 
CPH CME   H13   SING N N 41 
CPH "C2'" "O2'" DOUB N N 42 
CPH "C2'" "C3'" SING N N 43 
CPH "C3'" "O3'" SING N N 44 
CPH "C3'" "C4'" SING N N 45 
CPH "C3'" "H3'" SING N N 46 
CPH "O3'" HO3   SING N N 47 
CPH "C4'" "O4'" SING N N 48 
CPH "C4'" "C5'" SING N N 49 
CPH "C4'" "H4'" SING N N 50 
CPH "O4'" HO4   SING N N 51 
CPH "C5'" H51   SING N N 52 
CPH "C5'" H52   SING N N 53 
CPH "C5'" H53   SING N N 54 
# 
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 
CPH SMILES           ACDLabs              10.04 O=C(C(O)C(O)C)C(OC)C3C=C(O)C=2C(=O)c1c(O)c(ccc1CC=2C3)C                                                                                                        
CPH InChI            InChI                1.02b InChI=1/C21H24O7/c1-9-4-5-11-6-12-7-13(21(28-3)20(27)18(25)10(2)22)8-14(23)15(12)19(26)16(11)17(9)24/h4-5,8,10,13,18,21-25H,6-7H2,1-3H3/t10-,13-,18+,21+/m1/s1 
CPH InChIKey         InChI                1.02b HLGAJDCUXYQZBG-FAGSEQTRBW                                                                                                                                      
CPH SMILES_CANONICAL CACTVS               3.341 CO[C@@H]([C@@H]1CC2=C(C(=C1)O)C(=O)c3c(O)c(C)ccc3C2)C(=O)[C@@H](O)[C@@H](C)O                                                                                   
CPH SMILES           CACTVS               3.341 CO[CH]([CH]1CC2=C(C(=C1)O)C(=O)c3c(O)c(C)ccc3C2)C(=O)[CH](O)[CH](C)O                                                                                           
CPH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1ccc2c(c1O)C(=O)C3=C(C2)C[C@H](C=C3O)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC                                                                                       
CPH SMILES           "OpenEye OEToolkits" 1.5.0 Cc1ccc2c(c1O)C(=O)C3=C(C2)CC(C=C3O)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 
CPH "SYSTEMATIC NAME" ACDLabs              10.04 (1S)-5-deoxy-1-C-[(2R)-4,5-dihydroxy-6-methyl-10-oxo-1,2,9,10-tetrahydroanthracen-2-yl]-1-O-methyl-D-xylulose   
CPH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3R)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxo-pentyl]-1,8-dihydroxy-7-methyl-4,10-dihydro-3H-anthracen-9-one 
# 
