data_POD
# 
_chem_comp.id                                    POD 
_chem_comp.name                                  "9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONE" 
_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                         PODOPHYLLOTOXIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-03-04 
_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                     POD 
_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        1SA1 
_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 
POD O5   O5   O 0 1 N N N 115.817 88.087 9.521  -2.614 -1.787 2.116  O5   POD 1  
POD C13  C13  C 0 1 N N N 116.759 88.776 9.288  -2.808 -0.884 1.336  C13  POD 2  
POD O4   O4   O 0 1 N N N 117.856 89.097 10.154 -3.582 0.216  1.564  O4   POD 3  
POD C10  C10  C 0 1 N N R 116.860 89.602 8.132  -2.226 -0.754 -0.039 C10  POD 4  
POD C9   C9   C 0 1 N N R 118.162 90.326 8.185  -2.194 0.793  -0.246 C9   POD 5  
POD C12  C12  C 0 1 N N N 118.758 90.063 9.574  -3.535 1.137  0.420  C12  POD 6  
POD C11  C11  C 0 1 N N R 115.834 89.541 7.111  -0.800 -1.232 -0.224 C11  POD 7  
POD C5   C5   C 0 1 Y N N 116.034 90.758 6.281  -0.324 -0.766 -1.589 C5   POD 8  
POD C6   C6   C 0 1 Y N N 117.120 91.593 6.378  -0.926 0.247  -2.276 C6   POD 9  
POD C8   C8   C 0 1 N N R 118.301 91.595 7.350  -2.132 1.003  -1.747 C8   POD 10 
POD O3   O3   O 0 1 N N N 119.602 91.654 6.717  -1.994 2.397  -2.034 O3   POD 11 
POD C7   C7   C 0 1 Y N N 116.936 92.433 5.495  -0.462 0.637  -3.534 C7   POD 12 
POD C2   C2   C 0 1 Y N N 116.246 92.860 4.588  0.642  -0.017 -4.051 C2   POD 13 
POD C3   C3   C 0 1 Y N N 115.213 92.086 4.479  1.274  -1.041 -3.329 C3   POD 14 
POD C4   C4   C 0 1 Y N N 115.082 91.022 5.325  0.805  -1.426 -2.085 C4   POD 15 
POD O2   O2   O 0 1 N N N 116.249 93.936 3.642  1.291  0.153  -5.225 O2   POD 16 
POD C1   C1   C 0 1 N N N 115.044 93.761 2.862  2.094  -1.033 -5.398 C1   POD 17 
POD O1   O1   O 0 1 N N N 114.392 92.589 3.399  2.319  -1.504 -4.053 O1   POD 18 
POD C14  C14  C 0 1 Y N N 116.033 88.288 6.364  0.076  -0.644 0.850  C14  POD 19 
POD C15  C15  C 0 1 Y N N 115.267 87.207 6.729  0.312  -1.353 2.013  C15  POD 20 
POD C16  C16  C 0 1 Y N N 115.341 85.983 6.067  1.119  -0.816 3.004  C16  POD 21 
POD O6   O6   O 0 1 N N N 114.572 84.905 6.410  1.351  -1.515 4.147  O6   POD 22 
POD C20  C20  C 0 1 N N N 114.683 84.133 7.600  0.636  -2.747 4.030  C20  POD 23 
POD C17  C17  C 0 1 Y N N 116.189 85.821 5.025  1.687  0.440  2.830  C17  POD 24 
POD O7   O7   O 0 1 N N N 116.239 84.614 4.394  2.480  0.971  3.800  O7   POD 25 
POD C21  C21  C 0 1 N N N 115.209 83.638 4.238  1.625  1.718  4.668  C21  POD 26 
POD C18  C18  C 0 1 Y N N 116.958 86.884 4.652  1.452  1.148  1.657  C18  POD 27 
POD C19  C19  C 0 1 Y N N 116.898 88.119 5.302  0.644  0.603  0.671  C19  POD 28 
POD O8   O8   O 0 1 N N N 117.784 86.680 3.607  2.009  2.375  1.480  O8   POD 29 
POD C22  C22  C 0 1 N N N 117.422 87.296 2.370  1.581  2.842  0.198  C22  POD 30 
POD H10  H10  H 0 1 N N N 116.378 90.297 7.405  -2.880 -1.224 -0.774 H10  POD 31 
POD H9   H9   H 0 1 N N N 118.978 89.963 7.517  -1.353 1.262  0.264  H9   POD 32 
POD H121 1H12 H 0 0 N N N 118.911 90.979 10.190 -3.543 2.173  0.759  H121 POD 33 
POD H122 2H12 H 0 0 N N N 119.827 89.747 9.564  -4.365 0.948  -0.261 H122 POD 34 
POD H11  H11  H 0 1 N N N 114.788 89.530 7.497  -0.766 -2.320 -0.173 H11  POD 35 
POD H8   H8   H 0 1 N N N 118.259 92.523 7.965  -3.041 0.620  -2.211 H8   POD 36 
POD HO3  HO3  H 0 1 N N N 119.688 92.444 6.197  -1.959 2.481  -2.996 HO3  POD 37 
POD H7   H7   H 0 1 N N N 117.789 93.130 5.535  -0.950 1.425  -4.088 H7   POD 38 
POD H4   H4   H 0 1 N N N 114.197 90.368 5.235  1.287  -2.217 -1.528 H4   POD 39 
POD H11A 1H1  H 0 0 N N N 114.390 94.664 2.842  1.551  -1.779 -5.978 H11A POD 40 
POD H12  2H1  H 0 1 N N N 115.228 93.704 1.763  3.040  -0.787 -5.880 H12  POD 41 
POD H15  H15  H 0 1 N N N 114.572 87.325 7.577  -0.132 -2.328 2.149  H15  POD 42 
POD H201 1H20 H 0 0 N N N 114.056 83.254 7.879  0.792  -3.345 4.928  H201 POD 43 
POD H202 2H20 H 0 0 N N N 115.742 83.789 7.651  -0.427 -2.540 3.912  H202 POD 44 
POD H203 3H20 H 0 0 N N N 114.606 84.853 8.447  0.998  -3.296 3.160  H203 POD 45 
POD H211 1H21 H 0 0 N N N 115.249 82.650 3.721  2.218  2.165  5.466  H211 POD 46 
POD H212 2H21 H 0 0 N N N 114.851 83.417 5.270  1.129  2.505  4.100  H212 POD 47 
POD H213 3H21 H 0 0 N N N 114.355 84.181 3.770  0.876  1.055  5.100  H213 POD 48 
POD H19  H19  H 0 1 N N N 117.533 88.960 4.976  0.457  1.154  -0.238 H19  POD 49 
POD H221 1H22 H 0 0 N N N 118.105 87.127 1.505  2.005  3.829  0.011  H221 POD 50 
POD H222 2H22 H 0 0 N N N 116.385 86.992 2.091  1.919  2.149  -0.571 H222 POD 51 
POD H223 3H22 H 0 0 N N N 117.280 88.391 2.525  0.493  2.905  0.179  H223 POD 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 
POD O5  C13  DOUB N N 1  
POD C13 O4   SING N N 2  
POD C13 C10  SING N N 3  
POD O4  C12  SING N N 4  
POD C10 C9   SING N N 5  
POD C10 C11  SING N N 6  
POD C10 H10  SING N N 7  
POD C9  C12  SING N N 8  
POD C9  C8   SING N N 9  
POD C9  H9   SING N N 10 
POD C12 H121 SING N N 11 
POD C12 H122 SING N N 12 
POD C11 C5   SING N N 13 
POD C11 C14  SING N N 14 
POD C11 H11  SING N N 15 
POD C5  C6   SING Y N 16 
POD C5  C4   DOUB Y N 17 
POD C6  C8   SING N N 18 
POD C6  C7   DOUB Y N 19 
POD C8  O3   SING N N 20 
POD C8  H8   SING N N 21 
POD O3  HO3  SING N N 22 
POD C7  C2   SING Y N 23 
POD C7  H7   SING N N 24 
POD C2  C3   DOUB Y N 25 
POD C2  O2   SING N N 26 
POD C3  C4   SING Y N 27 
POD C3  O1   SING N N 28 
POD C4  H4   SING N N 29 
POD O2  C1   SING N N 30 
POD C1  O1   SING N N 31 
POD C1  H11A SING N N 32 
POD C1  H12  SING N N 33 
POD C14 C15  SING Y N 34 
POD C14 C19  DOUB Y N 35 
POD C15 C16  DOUB Y N 36 
POD C15 H15  SING N N 37 
POD C16 O6   SING N N 38 
POD C16 C17  SING Y N 39 
POD O6  C20  SING N N 40 
POD C20 H201 SING N N 41 
POD C20 H202 SING N N 42 
POD C20 H203 SING N N 43 
POD C17 O7   SING N N 44 
POD C17 C18  DOUB Y N 45 
POD O7  C21  SING N N 46 
POD C21 H211 SING N N 47 
POD C21 H212 SING N N 48 
POD C21 H213 SING N N 49 
POD C18 C19  SING Y N 50 
POD C18 O8   SING N N 51 
POD C19 H19  SING N N 52 
POD O8  C22  SING N N 53 
POD C22 H221 SING N N 54 
POD C22 H222 SING N N 55 
POD C22 H223 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 
POD SMILES           ACDLabs              10.04 O=C4OCC5C(O)c2cc1OCOc1cc2C(c3cc(OC)c(OC)c(OC)c3)C45                                                                                                                    
POD InChI            InChI                1.02b InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1 
POD InChIKey         InChI                1.02b YJGVMLPVUAXIQN-XVVDYKMHBO                                                                                                                                              
POD SMILES_CANONICAL CACTVS               3.341 COc1cc(cc(OC)c1OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](O)c4cc5OCOc5cc24                                                                                                    
POD SMILES           CACTVS               3.341 COc1cc(cc(OC)c1OC)[CH]2[CH]3[CH](COC3=O)[CH](O)c4cc5OCOc5cc24                                                                                                          
POD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5C2C(=O)OC5)O)OCO4                                                                                                     
POD SMILES           "OpenEye OEToolkits" 1.5.0 COc1cc(cc(c1OC)OC)C2c3cc4c(cc3C(C5C2C(=O)OC5)O)OCO4                                                                                                                    
# 
_pdbx_chem_comp_identifier.comp_id           POD 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        "(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one" 
# 
