data_LOC
# 
_chem_comp.id                                    LOC 
_chem_comp.name                                  N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H25 N O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         COLCHICINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-08-12 
_chem_comp.pdbx_modified_date                    2008-12-05 
_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                        399.437 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LOC 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3E22 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
LOC O4   O4   O 0 1 N N N 255.874 10.297 24.480 -1.225 2.491  -2.254 O4   LOC 1  
LOC C12  C12  C 0 1 N N N 255.335 10.433 25.556 -1.831 3.157  -1.442 C12  LOC 2  
LOC C13  C13  C 0 1 N N N 254.241 11.442 25.683 -2.839 4.177  -1.905 C13  LOC 3  
LOC N1   N1   N 0 1 N N N 255.588 9.774  26.683 -1.608 2.980  -0.124 N1   LOC 4  
LOC C11  C11  C 0 1 N N S 256.619 8.760  26.905 -0.632 1.985  0.326  C11  LOC 5  
LOC C14  C14  C 0 1 N N N 256.353 7.392  26.374 -1.307 0.631  0.402  C14  LOC 6  
LOC C15  C15  C 0 1 N N N 255.048 7.098  25.983 -2.649 0.637  0.478  C15  LOC 7  
LOC C10  C10  C 0 1 N N N 256.719 8.622  28.422 -0.076 2.411  1.670  C10  LOC 8  
LOC C9   C9   C 0 1 N N N 257.684 7.537  28.921 0.661  1.261  2.350  C9   LOC 9  
LOC C8   C8   C 0 1 Y N N 258.933 7.475  28.080 1.539  0.557  1.347  C8   LOC 10 
LOC C7   C7   C 0 1 Y N N 260.179 7.877  28.525 2.902  0.767  1.352  C7   LOC 11 
LOC C5   C5   C 0 1 Y N N 261.321 7.802  27.717 3.711  0.109  0.433  C5   LOC 12 
LOC C3   C3   C 0 1 Y N N 261.210 7.311  26.423 3.153  -0.764 -0.495 C3   LOC 13 
LOC C1   C1   C 0 1 Y N N 259.963 6.897  25.950 1.780  -0.977 -0.508 C1   LOC 14 
LOC O1   O1   O 0 1 N N N 259.886 6.425  24.683 1.227  -1.829 -1.411 O1   LOC 15 
LOC C2   C2   C 0 1 N N N 259.734 7.375  23.620 0.927  -1.298 -2.703 C2   LOC 16 
LOC O2   O2   O 0 1 N N N 262.337 7.228  25.623 3.951  -1.408 -1.389 O2   LOC 17 
LOC C4   C4   C 0 1 N N N 263.157 6.052  25.576 4.478  -2.676 -0.993 C4   LOC 18 
LOC O3   O3   O 0 1 N N N 262.514 8.256  28.261 5.053  0.320  0.441  O3   LOC 19 
LOC C6   C6   C 0 1 N N N 263.832 7.733  28.101 5.562  1.229  1.419  C6   LOC 20 
LOC C22  C22  C 0 1 Y N N 258.819 6.958  26.731 0.973  -0.307 0.416  C22  LOC 21 
LOC C21  C21  C 0 1 N N N 257.429 6.550  26.340 -0.506 -0.512 0.390  C21  LOC 22 
LOC C20  C20  C 0 1 N N N 257.084 5.436  25.966 -0.948 -1.810 0.361  C20  LOC 23 
LOC C19  C19  C 0 1 N N N 256.268 4.743  25.550 -2.179 -2.356 0.378  C19  LOC 24 
LOC C17  C17  C 0 1 N N N 255.119 4.599  25.178 -3.386 -1.735 0.459  C17  LOC 25 
LOC C16  C16  C 0 1 N N N 254.396 5.858  25.389 -3.582 -0.360 0.535  C16  LOC 26 
LOC O5   O5   O 0 1 N N N 253.227 5.906  25.046 -4.742 0.004  0.670  O5   LOC 27 
LOC O6   O6   O 0 1 N N N 254.564 3.420  24.587 -4.490 -2.521 0.467  O6   LOC 28 
LOC C18  C18  C 0 1 N N N 254.283 3.529  23.204 -4.282 -3.932 0.389  C18  LOC 29 
LOC H13  H13  H 0 1 N N N 254.092 11.690 26.744 -2.886 4.173  -2.994 H13  LOC 30 
LOC H13A H13A H 0 0 N N N 254.515 12.352 25.129 -3.820 3.929  -1.499 H13A LOC 31 
LOC H13B H13B H 0 0 N N N 253.310 11.027 25.269 -2.542 5.166  -1.558 H13B LOC 32 
LOC HN1  HN1  H 0 1 N N N 255.008 9.997  27.467 -2.093 3.513  0.525  HN1  LOC 33 
LOC H11  H11  H 0 1 N N N 257.517 9.105  26.371 0.184  1.936  -0.395 H11  LOC 34 
LOC H15  H15  H 0 1 N N N 254.360 7.917  26.132 -3.076 1.629  0.499  H15  LOC 35 
LOC H10  H10  H 0 1 N N N 257.069 9.586  28.821 0.615  3.242  1.524  H10  LOC 36 
LOC H10A H10A H 0 0 N N N 255.718 8.327  28.770 -0.896 2.738  2.309  H10A LOC 37 
LOC H9   H9   H 0 1 N N N 257.967 7.766  29.959 1.277  1.652  3.159  H9   LOC 38 
LOC H9A  H9A  H 0 1 N N N 257.174 6.565  28.854 -0.064 0.555  2.755  H9A  LOC 39 
LOC H7   H7   H 0 1 N N N 260.275 8.262  29.530 3.342  1.443  2.071  H7   LOC 40 
LOC H2   H2   H 0 1 N N N 259.695 8.391  24.039 0.285  -0.424 -2.597 H2   LOC 41 
LOC H2A  H2A  H 0 1 N N N 260.588 7.295  22.932 1.852  -1.012 -3.202 H2A  LOC 42 
LOC H2B  H2B  H 0 1 N N N 258.802 7.168  23.074 0.413  -2.055 -3.296 H2B  LOC 43 
LOC H4   H4   H 0 1 N N N 263.367 5.792  24.528 5.025  -3.118 -1.825 H4   LOC 44 
LOC H4A  H4A  H 0 1 N N N 264.103 6.244  26.103 5.150  -2.542 -0.146 H4A  LOC 45 
LOC H4B  H4B  H 0 1 N N N 262.629 5.218  26.061 3.659  -3.336 -0.706 H4B  LOC 46 
LOC H6   H6   H 0 1 N N N 264.046 7.598  27.030 5.317  0.863  2.417  H6   LOC 47 
LOC H6A  H6A  H 0 1 N N N 264.560 8.434  28.535 6.644  1.306  1.316  H6A  LOC 48 
LOC H6B  H6B  H 0 1 N N N 263.906 6.763  28.614 5.112  2.210  1.272  H6B  LOC 49 
LOC H20  H20  H 0 1 N N N 257.958 4.812  26.082 -0.152 -2.538 0.316  H20  LOC 50 
LOC H19  H19  H 0 1 N N N 256.735 3.776  25.438 -2.212 -3.434 0.319  H19  LOC 51 
LOC H18  H18  H 0 1 N N N 253.194 3.557  23.052 -3.758 -4.172 -0.537 H18  LOC 52 
LOC H18A H18A H 0 0 N N N 254.732 4.453  22.810 -3.684 -4.259 1.240  H18A LOC 53 
LOC H18B H18B H 0 0 N N N 254.705 2.662  22.675 -5.245 -4.443 0.404  H18B LOC 54 
# 
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 
LOC O4  C12  DOUB N N 1  
LOC C12 C13  SING N N 2  
LOC C12 N1   SING N N 3  
LOC N1  C11  SING N N 4  
LOC C11 C14  SING N N 5  
LOC C11 C10  SING N N 6  
LOC C14 C15  DOUB N N 7  
LOC C14 C21  SING N N 8  
LOC C15 C16  SING N N 9  
LOC C10 C9   SING N N 10 
LOC C9  C8   SING N N 11 
LOC C8  C7   DOUB N N 12 
LOC C8  C22  SING N N 13 
LOC C7  C5   SING N N 14 
LOC C5  C3   DOUB N N 15 
LOC C5  O3   SING N N 16 
LOC C3  C1   SING N N 17 
LOC C3  O2   SING N N 18 
LOC C1  O1   SING N N 19 
LOC C1  C22  DOUB N N 20 
LOC O1  C2   SING N N 21 
LOC O2  C4   SING Y N 22 
LOC O3  C6   SING Y N 23 
LOC C22 C21  SING Y N 24 
LOC C21 C20  DOUB N N 25 
LOC C20 C19  SING Y N 26 
LOC C19 C17  DOUB N N 27 
LOC C17 C16  SING Y N 28 
LOC C17 O6   SING N N 29 
LOC C16 O5   DOUB N N 30 
LOC O6  C18  SING Y N 31 
LOC C13 H13  SING N N 32 
LOC C13 H13A SING N N 33 
LOC C13 H13B SING N N 34 
LOC N1  HN1  SING N N 35 
LOC C11 H11  SING N N 36 
LOC C15 H15  SING N N 37 
LOC C10 H10  SING N N 38 
LOC C10 H10A SING N N 39 
LOC C9  H9   SING N N 40 
LOC C9  H9A  SING N N 41 
LOC C7  H7   SING N N 42 
LOC C2  H2   SING N N 43 
LOC C2  H2A  SING N N 44 
LOC C2  H2B  SING N N 45 
LOC C4  H4   SING N N 46 
LOC C4  H4A  SING N N 47 
LOC C4  H4B  SING N N 48 
LOC C6  H6   SING N N 49 
LOC C6  H6A  SING N N 50 
LOC C6  H6B  SING N N 51 
LOC C20 H20  SING N N 52 
LOC C19 H19  SING N N 53 
LOC C18 H18  SING N N 54 
LOC C18 H18A SING N N 55 
LOC C18 H18B SING N N 56 
# 
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 
LOC SMILES           ACDLabs              10.04 O=C(NC3C1=CC(=O)C(OC)=CC=C1c2c(cc(OC)c(OC)c2OC)CC3)C                                                                                                          
LOC InChI            InChI                1.02b InChI=1/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1/f/h23H 
LOC InChIKey         InChI                1.02b IAKHMKGGTNLKSZ-IKNPWOKSDD                                                                                                                                     
LOC SMILES_CANONICAL CACTVS               3.341 COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O                                                                                                      
LOC SMILES           CACTVS               3.341 COC1=CC=C2C(=CC1=O)[CH](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O                                                                                                       
LOC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@H]1CCc2cc(c(c(c2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC                                                                                                      
LOC SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1CCc2cc(c(c(c2C3=CC=C(C(=O)C=C13)OC)OC)OC)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 
LOC "SYSTEMATIC NAME" ACDLabs              10.04 N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide 
LOC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide   
# 
