data_CPB
# 
_chem_comp.id                                    CPB 
_chem_comp.name                                  2-(2-CHLORO-PHENYL)-5,7-DIHYDROXY-8-(3-HYDROXY-1-METHYL-PIPERIDIN-4-YL)-4H-BENZOPYRAN-4-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H20 Cl N O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FLAVOPIRIDOL 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-05-11 
_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                        401.840 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CPB 
_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        1C8K 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
CPB C1   C1   C  0 1 N N N 43.608 40.077 27.864 5.264  0.353  -1.011 C1   CPB 1  
CPB N1   N1   N  0 1 N N N 42.623 39.651 28.879 3.803  0.206  -0.976 N1   CPB 2  
CPB C16  C16  C  0 1 N N N 41.224 39.649 28.351 3.239  1.498  -1.382 C16  CPB 3  
CPB C15  C15  C  0 1 N N N 40.180 39.225 29.425 1.711  1.420  -1.377 C15  CPB 4  
CPB C14  C14  C  0 1 N N R 40.612 37.886 30.084 1.257  0.359  -2.384 C14  CPB 5  
CPB C13  C13  C  0 1 N N S 42.098 37.935 30.603 1.936  -0.970 -2.044 C13  CPB 6  
CPB C12  C12  C  0 1 N N N 43.026 38.318 29.419 3.452  -0.768 -2.015 C12  CPB 7  
CPB C8   C8   C  0 1 Y N N 39.535 37.513 31.138 -0.239 0.199  -2.307 C8   CPB 8  
CPB C9   C9   C  0 1 Y N N 38.699 36.415 30.815 -0.850 -0.012 -1.082 C9   CPB 9  
CPB O1   O1   O  0 1 Y N N 38.886 35.731 29.589 -0.123 -0.065 0.053  O1   CPB 10 
CPB C2   C2   C  0 1 Y N N 38.158 34.660 29.178 -0.685 -0.262 1.256  C2   CPB 11 
CPB C3   C3   C  0 1 Y N N 37.154 34.170 29.949 -2.025 -0.417 1.420  C3   CPB 12 
CPB C4   C4   C  0 1 Y N N 36.848 34.784 31.261 -2.877 -0.372 0.290  C4   CPB 13 
CPB O4   O4   O  0 1 N N N 35.961 34.338 31.954 -4.084 -0.508 0.400  O4   CPB 14 
CPB C10  C10  C  0 1 Y N N 37.684 35.978 31.716 -2.248 -0.155 -1.023 C10  CPB 15 
CPB C5   C5   C  0 1 Y N N 37.486 36.645 32.965 -3.013 -0.095 -2.194 C5   CPB 16 
CPB O5   O5   O  0 1 N N N 36.501 36.243 33.884 -4.361 -0.239 -2.139 O5   CPB 17 
CPB C6   C6   C  0 1 Y N N 38.312 37.746 33.285 -2.383 0.110  -3.409 C6   CPB 18 
CPB C7   C7   C  0 1 Y N N 39.336 38.183 32.392 -1.002 0.257  -3.463 C7   CPB 19 
CPB O7   O7   O  0 1 N N N 40.133 39.262 32.739 -0.394 0.459  -4.660 O7   CPB 20 
CPB C21  C21  C  0 1 Y N N 38.497 34.018 27.817 0.186  -0.312 2.447  C21  CPB 21 
CPB C22  C22  C  0 1 Y N N 38.923 34.806 26.674 -0.218 0.293  3.639  C22  CPB 22 
CPB CL1  CL1  CL 0 0 N N N 39.080 36.531 26.737 -1.752 1.102  3.728  CL1  CPB 23 
CPB C23  C23  C  0 1 Y N N 39.231 34.187 25.441 0.599  0.237  4.750  C23  CPB 24 
CPB C24  C24  C  0 1 Y N N 39.133 32.775 25.297 1.821  -0.406 4.681  C24  CPB 25 
CPB C25  C25  C  0 1 Y N N 38.709 31.977 26.417 2.230  -1.004 3.501  C25  CPB 26 
CPB C26  C26  C  0 1 Y N N 38.400 32.592 27.664 1.421  -0.961 2.385  C26  CPB 27 
CPB O3   O3   O  0 1 N N N 42.380 38.918 31.609 1.489  -1.422 -0.765 O3   CPB 28 
CPB H11  1H1  H  0 1 N N N 44.651 40.078 28.257 5.576  1.062  -0.244 H11  CPB 29 
CPB H12  2H1  H  0 1 N N N 43.527 39.456 26.941 5.731  -0.613 -0.824 H12  CPB 30 
CPB H13  3H1  H  0 1 N N N 43.339 41.070 27.435 5.569  0.720  -1.991 H13  CPB 31 
CPB H161 1H16 H  0 0 N N N 40.962 40.637 27.906 3.565  2.270  -0.685 H161 CPB 32 
CPB H162 2H16 H  0 0 N N N 41.141 39.013 27.438 3.586  1.746  -2.385 H162 CPB 33 
CPB H151 1H15 H  0 0 N N N 40.007 40.026 30.180 1.364  1.149  -0.380 H151 CPB 34 
CPB H152 2H15 H  0 0 N N N 39.147 39.171 29.006 1.296  2.389  -1.656 H152 CPB 35 
CPB H141 1H14 H  0 0 N N N 40.647 37.055 29.340 1.540  0.667  -3.390 H141 CPB 36 
CPB H131 1H13 H  0 0 N N N 42.265 36.923 31.041 1.683  -1.712 -2.802 H131 CPB 37 
CPB H121 1H12 H  0 0 N N N 43.045 37.532 28.628 3.788  -0.401 -2.984 H121 CPB 38 
CPB H122 2H12 H  0 0 N N N 44.104 38.287 29.702 3.941  -1.718 -1.799 H122 CPB 39 
CPB H31  1H3  H  0 1 N N N 36.609 33.308 29.526 -2.438 -0.574 2.406  H31  CPB 40 
CPB HO5  HO5  H  0 1 N N N 36.369 36.686 34.713 -4.545 -1.183 -2.234 HO5  CPB 41 
CPB H61  1H6  H  0 1 N N N 38.155 38.270 34.242 -2.966 0.157  -4.316 H61  CPB 42 
CPB HO7  HO7  H  0 1 N N N 40.001 39.705 33.568 -0.176 -0.413 -5.014 HO7  CPB 43 
CPB H231 1H23 H  0 0 N N N 39.549 34.808 24.587 0.286  0.700  5.674  H231 CPB 44 
CPB H241 1H24 H  0 0 N N N 39.382 32.305 24.330 2.459  -0.444 5.552  H241 CPB 45 
CPB H251 1H25 H  0 0 N N N 38.619 30.882 26.318 3.186  -1.505 3.455  H251 CPB 46 
CPB H261 1H26 H  0 0 N N N 38.084 31.962 28.513 1.742  -1.428 1.466  H261 CPB 47 
CPB HO3  HO3  H  0 1 N N N 43.276 38.947 31.922 1.939  -2.260 -0.591 HO3  CPB 48 
# 
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 
CPB C1  N1   SING N N 1  
CPB C1  H11  SING N N 2  
CPB C1  H12  SING N N 3  
CPB C1  H13  SING N N 4  
CPB N1  C16  SING N N 5  
CPB N1  C12  SING N N 6  
CPB C16 C15  SING N N 7  
CPB C16 H161 SING N N 8  
CPB C16 H162 SING N N 9  
CPB C15 C14  SING N N 10 
CPB C15 H151 SING N N 11 
CPB C15 H152 SING N N 12 
CPB C14 C13  SING N N 13 
CPB C14 C8   SING N N 14 
CPB C14 H141 SING N N 15 
CPB C13 C12  SING N N 16 
CPB C13 O3   SING N N 17 
CPB C13 H131 SING N N 18 
CPB C12 H121 SING N N 19 
CPB C12 H122 SING N N 20 
CPB C8  C9   DOUB Y N 21 
CPB C8  C7   SING Y N 22 
CPB C9  O1   SING Y N 23 
CPB C9  C10  SING Y N 24 
CPB O1  C2   SING Y N 25 
CPB C2  C3   DOUB Y N 26 
CPB C2  C21  SING N N 27 
CPB C3  C4   SING Y N 28 
CPB C3  H31  SING N N 29 
CPB C4  O4   DOUB N N 30 
CPB C4  C10  SING Y N 31 
CPB C10 C5   DOUB Y N 32 
CPB C5  O5   SING N N 33 
CPB C5  C6   SING Y N 34 
CPB O5  HO5  SING N N 35 
CPB C6  C7   DOUB Y N 36 
CPB C6  H61  SING N N 37 
CPB C7  O7   SING N N 38 
CPB O7  HO7  SING N N 39 
CPB C21 C22  DOUB Y N 40 
CPB C21 C26  SING Y N 41 
CPB C22 CL1  SING N N 42 
CPB C22 C23  SING Y N 43 
CPB C23 C24  DOUB Y N 44 
CPB C23 H231 SING N N 45 
CPB C24 C25  SING Y N 46 
CPB C24 H241 SING N N 47 
CPB C25 C26  DOUB Y N 48 
CPB C25 H251 SING N N 49 
CPB C26 H261 SING N N 50 
CPB O3  HO3  SING N N 51 
# 
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 
CPB SMILES           ACDLabs              10.04 Clc4ccccc4C=2Oc1c(c(O)cc(O)c1C(=O)C=2)C3CCN(C)CC3O                                                                                                               
CPB InChI            InChI                1.02b InChI=1/C21H20ClNO5/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3/t12-,17+/m0/s1 
CPB InChIKey         InChI                1.02b BIIVYFLTOXDAOV-YVEFUNNKBO                                                                                                                                        
CPB SMILES_CANONICAL CACTVS               3.341 CN1CC[C@@H]([C@H](O)C1)c2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccccc4Cl                                                                                                     
CPB SMILES           CACTVS               3.341 CN1CC[CH]([CH](O)C1)c2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccccc4Cl                                                                                                        
CPB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[N@]1CC[C@@H]([C@@H](C1)O)c2c(cc(c3c2OC(=CC3=O)c4ccccc4Cl)O)O                                                                                                   
CPB SMILES           "OpenEye OEToolkits" 1.5.0 CN1CCC(C(C1)O)c2c(cc(c3c2OC(=CC3=O)c4ccccc4Cl)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 
CPB "SYSTEMATIC NAME" ACDLabs              10.04 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4H-chromen-4-one 
CPB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(1S,3S,4R)-3-hydroxy-1-methyl-piperidin-4-yl]chromen-4-one 
# 
