data_4BC
# 
_chem_comp.id                                    4BC 
_chem_comp.name                                  "4-(1,3-BENZODIOXOL-5-YL)-5-(5-ETHYL-2,4-DIHYDROXYPHENYL)-2H-PYRAZOLE-3-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H16 N2 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-02-01 
_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                        368.340 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4BC 
_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        1YC1 
_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 
4BC C15  C15  C 0 1 Y N N 2.224  35.507 -4.374 0.653  -0.675 -1.927 C15  4BC 1  
4BC C12  C12  C 0 1 Y N N 2.919  36.284 -3.453 1.927  -0.373 -2.373 C12  4BC 2  
4BC O17  O17  O 0 1 N N N 4.255  36.526 -3.305 2.826  -1.099 -3.099 O17  4BC 3  
4BC C19  C19  C 0 1 N N N 4.394  37.379 -2.237 3.783  -0.144 -3.594 C19  4BC 4  
4BC O18  O18  O 0 1 N N N 3.158  37.664 -1.713 3.744  0.914  -2.618 O18  4BC 5  
4BC C16  C16  C 0 1 Y N N 2.237  36.982 -2.457 2.492  0.866  -2.077 C16  4BC 6  
4BC C22  C22  C 0 1 Y N N 0.851  36.912 -2.357 1.776  1.799  -1.341 C22  4BC 7  
4BC C20  C20  C 0 1 Y N N 0.162  36.126 -3.276 0.503  1.504  -0.899 C20  4BC 8  
4BC C8   C8   C 0 1 Y N N 0.838  35.428 -4.276 -0.067 0.265  -1.192 C8   4BC 9  
4BC C4   C4   C 0 1 Y N N 0.149  34.598 -5.160 -1.433 -0.051 -0.719 C4   4BC 10 
4BC C1   C1   C 0 1 Y N N 0.049  34.696 -6.542 -2.579 -0.240 -1.493 C1   4BC 11 
4BC C7   C7   C 0 1 N N N 0.667  35.746 -7.467 -2.678 -0.159 -2.954 C7   4BC 12 
4BC O21  O21  O 0 1 N N N 0.783  35.475 -8.662 -3.865 -0.361 -3.562 O21  4BC 13 
4BC O23  O23  O 0 1 N N N 1.043  36.837 -7.035 -1.690 0.091  -3.617 O23  4BC 14 
4BC N5   N5   N 0 1 Y N N -0.754 33.719 -6.962 -3.594 -0.510 -0.616 N5   4BC 15 
4BC C2   C2   C 0 1 Y N N -0.635 33.494 -4.843 -1.862 -0.239 0.618  C2   4BC 16 
4BC N3   N3   N 0 1 Y N N -1.139 33.047 -5.997 -3.150 -0.502 0.588  N3   4BC 17 
4BC C6   C6   C 0 1 Y N N -0.713 32.916 -3.576 -1.014 -0.148 1.831  C6   4BC 18 
4BC C10  C10  C 0 1 Y N N 0.428  32.719 -2.797 0.215  -0.801 1.874  C10  4BC 19 
4BC C14  C14  C 0 1 Y N N 0.337  32.203 -1.506 1.002  -0.714 3.004  C14  4BC 20 
4BC C26  C26  C 0 1 N N N 1.623  31.870 -0.744 2.332  -1.421 3.049  C26  4BC 21 
4BC C27  C27  C 0 1 N N N 1.939  30.377 -0.875 3.424  -0.485 2.527  C27  4BC 22 
4BC C13  C13  C 0 1 Y N N -0.912 31.909 -0.969 0.569  0.016  4.102  C13  4BC 23 
4BC O25  O25  O 0 1 N N N -1.008 31.625 0.361  1.349  0.097  5.212  O25  4BC 24 
4BC C11  C11  C 0 1 Y N N -2.055 32.072 -1.748 -0.651 0.673  4.065  C11  4BC 25 
4BC C9   C9   C 0 1 Y N N -1.951 32.565 -3.049 -1.447 0.592  2.936  C9   4BC 26 
4BC O24  O24  O 0 1 N N N -3.064 32.695 -3.816 -2.646 1.230  2.901  O24  4BC 27 
4BC H15  H15  H 0 1 N N N 2.763  34.963 -5.168 0.216  -1.637 -2.151 H15  4BC 28 
4BC H191 1H19 H 0 0 N N N 4.960  38.301 -2.506 3.482  0.226  -4.573 H191 4BC 29 
4BC H192 2H19 H 0 0 N N N 5.095  36.980 -1.468 4.777  -0.587 -3.639 H192 4BC 30 
4BC H22  H22  H 0 1 N N N 0.312  37.465 -1.569 2.216  2.758  -1.114 H22  4BC 31 
4BC H20  H20  H 0 1 N N N -0.937 36.055 -3.211 -0.051 2.233  -0.327 H20  4BC 32 
4BC H21  H21  H 0 1 N N N 1.167  36.127 -9.236 -3.929 -0.307 -4.526 H21  4BC 33 
4BC HN5  HN5  H 0 1 N N N -1.042 33.509 -7.917 -4.515 -0.683 -0.867 HN5  4BC 34 
4BC H10  H10  H 0 1 N N N 1.419  32.976 -3.209 0.552  -1.374 1.023  H10  4BC 35 
4BC H261 1H26 H 0 0 N N N 1.573  32.194 0.322  2.290  -2.314 2.425  H261 4BC 36 
4BC H262 2H26 H 0 0 N N N 2.478  32.508 -1.069 2.558  -1.706 4.077  H262 4BC 37 
4BC H271 1H27 H 0 0 N N N 1.989  30.053 -1.941 4.387  -0.996 2.559  H271 4BC 38 
4BC H272 2H27 H 0 0 N N N 2.875  30.135 -0.320 3.198  -0.200 1.499  H272 4BC 39 
4BC H273 3H27 H 0 0 N N N 1.084  29.739 -0.550 3.466  0.407  3.151  H273 4BC 40 
4BC H25  H25  H 0 1 N N N -1.861 31.424 0.728  1.094  -0.637 5.787  H25  4BC 41 
4BC H11  H11  H 0 1 N N N -3.043 31.810 -1.334 -0.983 1.245  4.920  H11  4BC 42 
4BC H24  H24  H 0 1 N N N -3.910 32.455 -3.456 -3.290 0.639  3.314  H24  4BC 43 
# 
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 
4BC C15 C12  DOUB Y N 1  
4BC C15 C8   SING Y N 2  
4BC C15 H15  SING N N 3  
4BC C12 O17  SING N N 4  
4BC C12 C16  SING Y N 5  
4BC O17 C19  SING N N 6  
4BC C19 O18  SING N N 7  
4BC C19 H191 SING N N 8  
4BC C19 H192 SING N N 9  
4BC O18 C16  SING N N 10 
4BC C16 C22  DOUB Y N 11 
4BC C22 C20  SING Y N 12 
4BC C22 H22  SING N N 13 
4BC C20 C8   DOUB Y N 14 
4BC C20 H20  SING N N 15 
4BC C8  C4   SING N N 16 
4BC C4  C1   DOUB Y N 17 
4BC C4  C2   SING Y N 18 
4BC C1  C7   SING N N 19 
4BC C1  N5   SING Y N 20 
4BC C7  O21  SING N N 21 
4BC C7  O23  DOUB N N 22 
4BC O21 H21  SING N N 23 
4BC N5  N3   SING Y N 24 
4BC N5  HN5  SING N N 25 
4BC C2  N3   DOUB Y N 26 
4BC C2  C6   SING N N 27 
4BC C6  C10  DOUB Y N 28 
4BC C6  C9   SING Y N 29 
4BC C10 C14  SING Y N 30 
4BC C10 H10  SING N N 31 
4BC C14 C26  SING N N 32 
4BC C14 C13  DOUB Y N 33 
4BC C26 C27  SING N N 34 
4BC C26 H261 SING N N 35 
4BC C26 H262 SING N N 36 
4BC C27 H271 SING N N 37 
4BC C27 H272 SING N N 38 
4BC C27 H273 SING N N 39 
4BC C13 O25  SING N N 40 
4BC C13 C11  SING Y N 41 
4BC O25 H25  SING N N 42 
4BC C11 C9   DOUB Y N 43 
4BC C11 H11  SING N N 44 
4BC C9  O24  SING N N 45 
4BC O24 H24  SING N N 46 
# 
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 
4BC SMILES           ACDLabs              10.04 O=C(O)c4nnc(c1cc(c(O)cc1O)CC)c4c2ccc3OCOc3c2                                                                                                              
4BC InChI            InChI                1.02b InChI=1/C19H16N2O6/c1-2-9-5-11(13(23)7-12(9)22)17-16(18(19(24)25)21-20-17)10-3-4-14-15(6-10)27-8-26-14/h3-7,22-23H,2,8H2,1H3,(H,20,21)(H,24,25)/f/h21,24H 
4BC InChIKey         InChI                1.02b LCTWZJKHOGKNMX-GWZBNUJDCP                                                                                                                                 
4BC SMILES_CANONICAL CACTVS               3.341 CCc1cc(c(O)cc1O)c2n[nH]c(C(O)=O)c2c3ccc4OCOc4c3                                                                                                           
4BC SMILES           CACTVS               3.341 CCc1cc(c(O)cc1O)c2n[nH]c(C(O)=O)c2c3ccc4OCOc4c3                                                                                                           
4BC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1cc(c(cc1O)O)c2c(c([nH]n2)C(=O)O)c3ccc4c(c3)OCO4                                                                                                       
4BC SMILES           "OpenEye OEToolkits" 1.5.0 CCc1cc(c(cc1O)O)c2c(c([nH]n2)C(=O)O)c3ccc4c(c3)OCO4                                                                                                       
# 
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 
4BC "SYSTEMATIC NAME" ACDLabs              10.04 "4-(1,3-benzodioxol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-pyrazole-5-carboxylic acid"  
4BC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-(1,3-benzodioxol-5-yl)-5-(5-ethyl-2,4-dihydroxy-phenyl)-2H-pyrazole-3-carboxylic acid" 
# 
