data_AKV
# 
_chem_comp.id                                    AKV 
_chem_comp.name                                  {3-[(1R,3S)-1,3-DIHYDROXYPENTYL]-4,5,9,10-TETRAHYDROXY-2-ANTHRYL}ACETATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "DERIVATIVE OF AKLANONIC ACID METHYL ESTER (AAME)" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-07 
_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                        414.405 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AKV 
_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        2F99 
_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 
AKV O20  O20  O 0 1 N N N 15.619 7.150  16.691 -2.427 1.866  1.442  O20  AKV 1  
AKV C5   C5   C 0 1 N N N 15.943 7.550  15.551 -2.513 0.930  0.670  C5   AKV 2  
AKV C17  C17  C 0 1 Y N N 16.120 6.621  14.511 -1.305 0.189  0.258  C17  AKV 3  
AKV C6   C6   C 0 1 Y N N 15.933 5.237  14.738 -0.033 0.708  0.508  C6   AKV 4  
AKV O21  O21  O 0 1 N N N 15.573 4.801  15.977 0.105  1.902  1.136  O21  AKV 5  
AKV C16  C16  C 0 1 Y N N 16.127 8.926  15.336 -3.827 0.523  0.135  C16  AKV 6  
AKV C4   C4   C 0 1 Y N N 15.954 9.852  16.378 -4.938 1.359  0.266  C4   AKV 7  
AKV O19  O19  O 0 1 N N N 15.597 9.427  17.625 -4.820 2.557  0.889  O19  AKV 8  
AKV C3   C3   C 0 1 Y N N 16.136 11.220 16.155 -6.168 0.954  -0.246 C3   AKV 9  
AKV C2   C2   C 0 1 Y N N 16.505 11.665 14.888 -6.293 -0.264 -0.881 C2   AKV 10 
AKV C1   C1   C 0 1 Y N N 16.684 10.751 13.848 -5.199 -1.103 -1.019 C1   AKV 11 
AKV C21  C21  C 0 1 Y N N 16.498 9.381  14.069 -3.962 -0.718 -0.516 C21  AKV 12 
AKV C12  C12  C 0 1 N N N 16.676 8.467  13.027 -2.784 -1.601 -0.658 C12  AKV 13 
AKV O18  O18  O 0 1 N N N 17.002 8.889  11.886 -2.921 -2.763 -0.988 O18  AKV 14 
AKV C18  C18  C 0 1 Y N N 16.489 7.093  13.245 -1.436 -1.052 -0.395 C18  AKV 15 
AKV C11  C11  C 0 1 Y N N 16.671 6.195  12.185 -0.299 -1.750 -0.785 C11  AKV 16 
AKV C19  C19  C 0 1 Y N N 16.501 4.823  12.361 0.958  -1.220 -0.536 C19  AKV 17 
AKV C10  C10  C 0 1 N N N 16.700 3.923  11.192 2.187  -1.981 -0.961 C10  AKV 18 
AKV C14  C14  C 0 1 N N N 18.034 3.456  11.083 2.696  -2.801 0.197  C14  AKV 19 
AKV O16  O16  O 0 1 N N N 18.434 2.236  11.783 3.789  -3.565 0.049  O16  AKV 20 
AKV C15  C15  C 0 1 N N N 19.229 1.406  10.932 4.280  -4.354 1.165  C15  AKV 21 
AKV O17  O17  O 0 1 N N N 18.896 4.209  10.657 2.120  -2.769 1.259  O17  AKV 22 
AKV C20  C20  C 0 1 Y N N 16.095 4.299  13.713 1.093  -0.008 0.109  C20  AKV 23 
AKV C7   C7   C 0 1 N N R 15.908 2.800  13.930 2.468  0.548  0.377  C7   AKV 24 
AKV O22  O22  O 0 1 N N N 15.661 2.165  12.710 2.539  1.012  1.726  O22  AKV 25 
AKV C8   C8   C 0 1 N N N 14.833 2.360  14.851 2.743  1.712  -0.578 C8   AKV 26 
AKV C9   C9   C 0 1 N N S 14.634 0.951  14.767 4.182  2.196  -0.392 C9   AKV 27 
AKV O23  O23  O 0 1 N N N 15.519 0.203  14.208 5.087  1.162  -0.786 O23  AKV 28 
AKV C13  C13  C 0 1 N N N 13.564 0.322  15.421 4.419  3.437  -1.254 C13  AKV 29 
AKV C22  C22  C 0 1 N N N 13.507 -1.045 15.039 5.816  3.994  -0.975 C22  AKV 30 
AKV H21  H21  H 0 1 N N N 15.489 3.855  15.968 0.118  2.580  0.447  H21  AKV 31 
AKV H19  H19  H 0 1 N N N 15.514 8.481  17.626 -4.591 3.205  0.209  H19  AKV 32 
AKV H3   H3   H 0 1 N N N 15.992 11.926 16.959 -7.029 1.598  -0.146 H3   AKV 33 
AKV H2   H2   H 0 1 N N N 16.653 12.720 14.710 -7.253 -0.567 -1.274 H2   AKV 34 
AKV H1   H1   H 0 1 N N N 16.968 11.103 12.867 -5.307 -2.055 -1.518 H1   AKV 35 
AKV H11  H11  H 0 1 N N N 16.949 6.574  11.212 -0.395 -2.702 -1.285 H11  AKV 36 
AKV H101 1H10 H 0 0 N N N 16.472 4.500  10.283 1.936  -2.642 -1.791 H101 AKV 37 
AKV H102 2H10 H 0 0 N N N 16.036 3.054  11.306 2.958  -1.279 -1.276 H102 AKV 38 
AKV H151 1H15 H 0 0 N N N 18.686 0.474  10.718 5.169  -4.905 0.857  H151 AKV 39 
AKV H152 2H15 H 0 0 N N N 20.179 1.171  11.433 4.531  -3.694 1.995  H152 AKV 40 
AKV H153 3H15 H 0 0 N N N 19.433 1.935  9.990  3.508  -5.057 1.480  H153 AKV 41 
AKV H7   H7   H 0 1 N N N 16.857 2.519  14.410 3.213  -0.233 0.221  H7   AKV 42 
AKV H22  H22  H 0 1 N N N 15.605 2.815  12.020 1.962  1.785  1.787  H22  AKV 43 
AKV H81  1H8  H 0 1 N N N 13.898 2.865  14.566 2.054  2.529  -0.362 H81  AKV 44 
AKV H82  2H8  H 0 1 N N N 15.116 2.620  15.882 2.601  1.380  -1.606 H82  AKV 45 
AKV H9   H9   H 0 1 N N N 14.034 1.333  13.928 4.349  2.445  0.656  H9   AKV 46 
AKV H23  H23  H 0 1 N N N 15.259 0.019  13.313 4.906  0.973  -1.717 H23  AKV 47 
AKV H131 1H13 H 0 0 N N N 12.623 0.818  15.141 3.671  4.194  -1.015 H131 AKV 48 
AKV H132 2H13 H 0 0 N N N 13.709 0.392  16.509 4.339  3.168  -2.308 H132 AKV 49 
AKV H221 1H22 H 0 0 N N N 12.595 -1.502 15.449 5.896  4.263  0.078  H221 AKV 50 
AKV H222 2H22 H 0 0 N N N 14.390 -1.572 15.430 6.563  3.237  -1.214 H222 AKV 51 
AKV H223 3H22 H 0 0 N N N 13.492 -1.119 13.942 5.985  4.878  -1.589 H223 AKV 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 
AKV O20 C5   DOUB N N 1  
AKV C5  C17  SING N N 2  
AKV C5  C16  SING N N 3  
AKV C17 C6   SING Y N 4  
AKV C17 C18  DOUB Y N 5  
AKV C6  O21  SING N N 6  
AKV C6  C20  DOUB Y N 7  
AKV O21 H21  SING N N 8  
AKV C16 C4   DOUB Y N 9  
AKV C16 C21  SING Y N 10 
AKV C4  O19  SING N N 11 
AKV C4  C3   SING Y N 12 
AKV O19 H19  SING N N 13 
AKV C3  C2   DOUB Y N 14 
AKV C3  H3   SING N N 15 
AKV C2  C1   SING Y N 16 
AKV C2  H2   SING N N 17 
AKV C1  C21  DOUB Y N 18 
AKV C1  H1   SING N N 19 
AKV C21 C12  SING N N 20 
AKV C12 O18  DOUB N N 21 
AKV C12 C18  SING N N 22 
AKV C18 C11  SING Y N 23 
AKV C11 C19  DOUB Y N 24 
AKV C11 H11  SING N N 25 
AKV C19 C10  SING N N 26 
AKV C19 C20  SING Y N 27 
AKV C10 C14  SING N N 28 
AKV C10 H101 SING N N 29 
AKV C10 H102 SING N N 30 
AKV C14 O16  SING N N 31 
AKV C14 O17  DOUB N N 32 
AKV O16 C15  SING N N 33 
AKV C15 H151 SING N N 34 
AKV C15 H152 SING N N 35 
AKV C15 H153 SING N N 36 
AKV C20 C7   SING N N 37 
AKV C7  O22  SING N N 38 
AKV C7  C8   SING N N 39 
AKV C7  H7   SING N N 40 
AKV O22 H22  SING N N 41 
AKV C8  C9   SING N N 42 
AKV C8  H81  SING N N 43 
AKV C8  H82  SING N N 44 
AKV C9  O23  SING N N 45 
AKV C9  C13  SING N N 46 
AKV C9  H9   SING N N 47 
AKV O23 H23  SING N N 48 
AKV C13 C22  SING N N 49 
AKV C13 H131 SING N N 50 
AKV C13 H132 SING N N 51 
AKV C22 H221 SING N N 52 
AKV C22 H222 SING N N 53 
AKV C22 H223 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 
AKV SMILES           ACDLabs              10.04 O=C2c1cccc(O)c1C(=O)c3c2cc(c(c3O)C(O)CC(O)CC)CC(=O)OC                                                                                                         
AKV InChI            InChI                1.02b InChI=1/C22H22O8/c1-3-11(23)9-15(25)17-10(8-16(26)30-2)7-13-19(21(17)28)22(29)18-12(20(13)27)5-4-6-14(18)24/h4-7,11,15,23-25,28H,3,8-9H2,1-2H3/t11-,15+/m0/s1 
AKV InChIKey         InChI                1.02b SIHNJMGWRHPFAZ-XHDPSFHLBH                                                                                                                                     
AKV SMILES_CANONICAL CACTVS               3.341 CC[C@H](O)C[C@@H](O)c1c(O)c2C(=O)c3c(O)cccc3C(=O)c2cc1CC(=O)OC                                                                                                
AKV SMILES           CACTVS               3.341 CC[CH](O)C[CH](O)c1c(O)c2C(=O)c3c(O)cccc3C(=O)c2cc1CC(=O)OC                                                                                                   
AKV SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC(C[C@H](c1c(cc2c(c1O)C(=O)c3c(cccc3O)C2=O)CC(=O)OC)O)O                                                                                                     
AKV SMILES           "OpenEye OEToolkits" 1.5.0 CCC(CC(c1c(cc2c(c1O)C(=O)c3c(cccc3O)C2=O)CC(=O)OC)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 
AKV "SYSTEMATIC NAME" ACDLabs              10.04 "methyl {3-[(1R,3S)-1,3-dihydroxypentyl]-4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl}acetate" 
AKV "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl 2-[3-[(1R)-1,3-dihydroxypentyl]-4,5-dihydroxy-9,10-dioxo-anthracen-2-yl]ethanoate"            
# 
