data_458
# 
_chem_comp.id                                    458 
_chem_comp.name                                  4-[(1S,2S,5S)-5-(HYDROXYMETHYL)-8-METHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H20 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-30 
_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                        260.328 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     458 
_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        2B1V 
_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 
458 CAK  CAK  C 0 1 N N N -5.390 -4.960 18.311 -2.037 -0.072 -1.503 CAK  458 1  
458 CAJ  CAJ  C 0 1 N N S -4.625 -4.515 19.576 -0.577 0.291  -1.193 CAJ  458 2  
458 CAO  CAO  C 0 1 N N N -5.603 -3.664 20.322 -0.564 1.555  -0.369 CAO  458 3  
458 CAR  CAR  C 0 1 N N N -5.203 -2.313 20.920 0.666  2.426  -0.405 CAR  458 4  
458 CAQ  CAQ  C 0 1 N N N -6.887 -4.177 20.420 -1.564 1.925  0.365  CAQ  458 5  
458 CAP  CAP  C 0 1 N N N -7.317 -5.395 19.892 -2.859 1.181  0.485  CAP  458 6  
458 CAL  CAL  C 0 1 N N S -6.410 -5.995 18.788 -2.766 -0.198 -0.160 CAL  458 7  
458 CAT  CAT  C 0 1 N N N -7.278 -6.540 17.634 -4.180 -0.727 -0.409 CAT  458 8  
458 OAU  OAU  O 0 1 N N N -8.074 -5.485 17.044 -4.880 -0.821 0.834  OAU  458 9  
458 CAM  CAM  C 0 1 N N N -5.610 -7.125 19.392 -2.022 -1.178 0.737  CAM  458 10 
458 OAH  OAH  O 0 1 N N N -5.274 -6.644 20.711 -0.670 -0.779 0.938  OAH  458 11 
458 CAI  CAI  C 0 1 N N S -4.234 -5.703 20.516 -0.008 -0.824 -0.327 CAI  458 12 
458 CAD  CAD  C 0 1 Y N N -3.622 -5.215 21.847 1.471  -0.609 -0.135 CAD  458 13 
458 CAC  CAC  C 0 1 Y N N -4.439 -4.912 22.961 2.360  -1.012 -1.115 CAC  458 14 
458 CAB  CAB  C 0 1 Y N N -3.841 -4.468 24.155 3.716  -0.811 -0.944 CAB  458 15 
458 CAA  CAA  C 0 1 Y N N -2.433 -4.355 24.212 4.187  -0.215 0.217  CAA  458 16 
458 OAG  OAG  O 0 1 N N N -1.858 -3.924 25.367 5.521  -0.021 0.390  OAG  458 17 
458 CAF  CAF  C 0 1 Y N N -1.611 -4.652 23.104 3.293  0.183  1.201  CAF  458 18 
458 CAE  CAE  C 0 1 Y N N -2.224 -5.085 21.902 1.938  -0.015 1.023  CAE  458 19 
458 HAK1 1HAK H 0 0 N N N -5.879 -4.109 17.814 -2.078 -1.016 -2.047 HAK1 458 20 
458 HAK2 2HAK H 0 0 N N N -4.702 -5.401 17.574 -2.499 0.719  -2.094 HAK2 458 21 
458 HAJ  HAJ  H 0 1 N N N -3.689 -4.017 19.284 -0.005 0.402  -2.115 HAJ  458 22 
458 HAR1 1HAR H 0 0 N N N -5.974 -1.565 20.684 0.480  3.339  0.160  HAR1 458 23 
458 HAR2 2HAR H 0 0 N N N -4.240 -1.994 20.494 1.505  1.888  0.038  HAR2 458 24 
458 HAR3 3HAR H 0 0 N N N -5.107 -2.409 22.012 0.901  2.679  -1.438 HAR3 458 25 
458 HAQ  HAQ  H 0 1 N N N -7.617 -3.583 20.950 -1.457 2.838  0.932  HAQ  458 26 
458 HAP1 1HAP H 0 0 N N N -8.290 -5.198 19.418 -3.108 1.067  1.540  HAP1 458 27 
458 HAP2 2HAP H 0 0 N N N -7.358 -6.120 20.719 -3.646 1.753  -0.007 HAP2 458 28 
458 HAT1 1HAT H 0 0 N N N -7.954 -7.309 18.035 -4.711 -0.046 -1.074 HAT1 458 29 
458 HAT2 2HAT H 0 0 N N N -6.621 -6.967 16.862 -4.123 -1.714 -0.869 HAT2 458 30 
458 HAU  HAU  H 0 1 N N N -8.248 -4.817 17.696 -5.764 -1.158 0.632  HAU  458 31 
458 HAM1 1HAM H 0 0 N N N -4.721 -7.379 18.796 -2.525 -1.230 1.703  HAM1 458 32 
458 HAM2 2HAM H 0 0 N N N -6.200 -8.052 19.441 -2.037 -2.165 0.276  HAM2 458 33 
458 HAI  HAI  H 0 1 N N N -3.446 -6.254 19.981 -0.181 -1.791 -0.799 HAI  458 34 
458 HAC  HAC  H 0 1 N N N -5.512 -5.020 22.896 1.993  -1.476 -2.018 HAC  458 35 
458 HAB  HAB  H 0 1 N N N -4.447 -4.218 25.013 4.409  -1.121 -1.711 HAB  458 36 
458 HAG  HAG  H 0 1 N N N -0.922 -3.824 25.237 5.864  -0.814 0.825  HAG  458 37 
458 HAF  HAF  H 0 1 N N N -0.538 -4.551 23.171 3.657  0.648  2.106  HAF  458 38 
458 HAE  HAE  H 0 1 N N N -1.622 -5.313 21.035 1.242  0.294  1.789  HAE  458 39 
# 
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 
458 CAK CAJ  SING N N 1  
458 CAK CAL  SING N N 2  
458 CAK HAK1 SING N N 3  
458 CAK HAK2 SING N N 4  
458 CAJ CAO  SING N N 5  
458 CAJ CAI  SING N N 6  
458 CAJ HAJ  SING N N 7  
458 CAO CAR  SING N N 8  
458 CAO CAQ  DOUB N N 9  
458 CAR HAR1 SING N N 10 
458 CAR HAR2 SING N N 11 
458 CAR HAR3 SING N N 12 
458 CAQ CAP  SING N N 13 
458 CAQ HAQ  SING N N 14 
458 CAP CAL  SING N N 15 
458 CAP HAP1 SING N N 16 
458 CAP HAP2 SING N N 17 
458 CAL CAT  SING N N 18 
458 CAL CAM  SING N N 19 
458 CAT OAU  SING N N 20 
458 CAT HAT1 SING N N 21 
458 CAT HAT2 SING N N 22 
458 OAU HAU  SING N N 23 
458 CAM OAH  SING N N 24 
458 CAM HAM1 SING N N 25 
458 CAM HAM2 SING N N 26 
458 OAH CAI  SING N N 27 
458 CAI CAD  SING N N 28 
458 CAI HAI  SING N N 29 
458 CAD CAC  SING Y N 30 
458 CAD CAE  DOUB Y N 31 
458 CAC CAB  DOUB Y N 32 
458 CAC HAC  SING N N 33 
458 CAB CAA  SING Y N 34 
458 CAB HAB  SING N N 35 
458 CAA OAG  SING N N 36 
458 CAA CAF  DOUB Y N 37 
458 OAG HAG  SING N N 38 
458 CAF CAE  SING Y N 39 
458 CAF HAF  SING N N 40 
458 CAE HAE  SING N N 41 
# 
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 
458 SMILES           ACDLabs              10.04 Oc1ccc(cc1)C2OCC3(CC=C(C2C3)C)CO                                                                                           
458 InChI            InChI                1.02b InChI=1/C16H20O3/c1-11-6-7-16(9-17)8-14(11)15(19-10-16)12-2-4-13(18)5-3-12/h2-6,14-15,17-18H,7-10H2,1H3/t14-,15+,16-/m0/s1 
458 InChIKey         InChI                1.02b XXIFNRNIQJKFLP-XHSDSOJGBU                                                                                                  
458 SMILES_CANONICAL CACTVS               3.341 CC1=CC[C@]2(CO)CO[C@@H]([C@H]1C2)c3ccc(O)cc3                                                                               
458 SMILES           CACTVS               3.341 CC1=CC[C]2(CO)CO[CH]([CH]1C2)c3ccc(O)cc3                                                                                   
458 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CC[C@]2(C[C@@H]1[C@H](OC2)c3ccc(cc3)O)CO                                                                               
458 SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CCC2(CC1C(OC2)c3ccc(cc3)O)CO                                                                                           
# 
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 
458 "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1S,2S,5S)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol 
458 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1S,2S,5S)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol 
# 
