data_TN4
# 
_chem_comp.id                                    TN4 
_chem_comp.name                                  "(CHLOROACETYL)CARBAMIC ACID (3R,4S,5S,5R)-5-METHOXY-4-[(2R,3R)-2-METHYL-3-(3-METHYL-2-BUTENYL)OXIRANYL]-1-OXASPIRO[2.5]OCT-6-YL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H28 Cl N O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         TNP-470 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-04-24 
_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                        401.882 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TN4 
_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        1B6A 
_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 
TN4 N42  N42  N  0 1 N N N 15.005 30.553 23.025 -0.844 0.130  3.662  N42  TN4 1  
TN4 C41  C41  C  0 1 N N N 15.162 29.324 22.527 0.347  -0.100 3.077  C41  TN4 2  
TN4 O4A  O4A  O  0 1 N N N 14.463 28.346 22.732 1.314  -0.378 3.757  O4A  TN4 3  
TN4 O41  O41  O  0 1 N N N 16.254 29.228 21.793 0.466  -0.023 1.738  O41  TN4 4  
TN4 C4   C4   C  0 1 N N R 16.403 28.123 20.853 1.750  -0.272 1.107  C4   TN4 5  
TN4 C5   C5   C  0 1 N N N 17.855 27.625 20.876 2.526  1.040  1.004  C5   TN4 6  
TN4 C6   C6   C  0 1 N N N 18.808 28.698 20.355 1.695  2.065  0.226  C6   TN4 7  
TN4 C1   C1   C  0 1 N N R 18.391 29.209 18.975 1.341  1.479  -1.142 C1   TN4 8  
TN4 O11  O11  O  0 1 N N N 18.473 28.177 18.098 2.206  1.770  -2.238 O11  TN4 9  
TN4 C11  C11  C  0 1 N N N 19.420 30.261 18.522 0.948  2.447  -2.256 C11  TN4 10 
TN4 C2   C2   C  0 1 N N S 16.941 29.759 19.006 0.661  0.108  -1.109 C2   TN4 11 
TN4 C3   C3   C  0 1 N N S 15.989 28.621 19.447 1.525  -0.854 -0.288 C3   TN4 12 
TN4 O31  O31  O  0 1 N N N 14.664 29.116 19.496 0.861  -2.114 -0.179 O31  TN4 13 
TN4 C31  C31  C  0 1 N N N 13.701 28.052 19.506 1.881  -3.111 -0.079 C31  TN4 14 
TN4 C21  C21  C  0 1 N N R 16.496 30.329 17.675 0.510  -0.422 -2.536 C21  TN4 15 
TN4 O2A  O2A  O  0 1 N N N 15.432 31.303 17.844 -0.623 -1.242 -2.824 O2A  TN4 16 
TN4 C22  C22  C  0 1 N N R 16.648 31.863 17.543 -0.673 0.082  -3.363 C22  TN4 17 
TN4 C23  C23  C  0 1 N N N 16.841 32.395 16.141 -0.472 0.246  -4.871 C23  TN4 18 
TN4 C24  C24  C  0 1 N N N 18.192 32.076 15.557 -1.765 0.688  -5.505 C24  TN4 19 
TN4 C25  C25  C  0 1 N N N 19.361 32.717 15.552 -2.250 0.033  -6.531 C25  TN4 20 
TN4 C2B  C2B  C  0 1 N N N 20.663 32.068 15.143 -3.643 0.327  -7.023 C2B  TN4 21 
TN4 C2C  C2C  C  0 1 N N N 19.533 34.054 16.263 -1.413 -1.015 -7.218 C2C  TN4 22 
TN4 C2A  C2A  C  0 1 N N N 16.103 29.455 16.512 1.816  -0.728 -3.272 C2A  TN4 23 
TN4 C43  C43  C  0 1 N N N 14.004 30.980 23.816 -0.962 0.053  5.003  C43  TN4 24 
TN4 O4B  O4B  O  0 1 N N N 13.064 30.329 24.259 0.002  -0.223 5.682  O4B  TN4 25 
TN4 C44  C44  C  0 1 N N N 14.161 32.459 24.146 -2.295 0.311  5.657  C44  TN4 26 
TN4 CL4  CL4  CL 0 0 N N N 14.144 32.690 25.918 -2.131 0.134  7.444  CL4  TN4 27 
TN4 H42  H42  H  0 1 N N N 15.722 31.234 22.776 -1.616 0.352  3.119  H42  TN4 28 
TN4 H4   H4   H  0 1 N N N 15.748 27.265 21.135 2.317  -0.982 1.709  H4   TN4 29 
TN4 H51  1H5  H  0 1 N N N 18.151 27.267 21.889 3.468  0.866  0.484  H51  TN4 30 
TN4 H52  2H5  H  0 1 N N N 17.970 26.666 20.318 2.730  1.422  2.005  H52  TN4 31 
TN4 H61  1H6  H  0 1 N N N 18.912 29.535 21.083 2.273  2.979  0.093  H61  TN4 32 
TN4 H62  2H6  H  0 1 N N N 19.862 28.336 20.351 0.780  2.286  0.776  H62  TN4 33 
TN4 H111 1H11 H  0 0 N N N 19.703 31.295 18.217 0.202  2.115  -2.978 H111 TN4 34 
TN4 H112 2H11 H  0 0 N N N 20.294 30.927 18.705 0.941  3.512  -2.024 H112 TN4 35 
TN4 H2   H2   H  0 1 N N N 16.910 30.604 19.732 -0.321 0.200  -0.647 H2   TN4 36 
TN4 H3   H3   H  0 1 N N N 16.048 27.777 18.720 2.487  -0.991 -0.783 H3   TN4 37 
TN4 H311 1H31 H  0 0 N N N 12.657 28.442 19.544 1.420  -4.095 0.007  H311 TN4 38 
TN4 H312 2H31 H  0 0 N N N 13.846 27.363 18.641 2.508  -3.080 -0.970 H312 TN4 39 
TN4 H313 3H31 H  0 0 N N N 13.897 27.333 20.335 2.492  -2.917 0.802  H313 TN4 40 
TN4 H22  H22  H  0 1 N N N 17.289 32.647 18.009 -1.351 0.795  -2.896 H22  TN4 41 
TN4 H231 1H23 H  0 0 N N N 16.026 32.038 15.468 -0.163 -0.706 -5.302 H231 TN4 42 
TN4 H232 2H23 H  0 0 N N N 16.644 33.492 16.105 0.297  0.995  -5.055 H232 TN4 43 
TN4 H24  H24  H  0 1 N N N 18.368 31.143 14.994 -2.293 1.545  -5.114 H24  TN4 44 
TN4 H2B1 1H2B H  0 0 N N N 21.640 32.604 15.138 -3.869 -0.310 -7.877 H2B1 TN4 45 
TN4 H2B2 2H2B H  0 0 N N N 20.788 31.154 15.769 -4.359 0.133  -6.225 H2B2 TN4 46 
TN4 H2B3 3H2B H  0 0 N N N 20.514 31.641 14.123 -3.709 1.373  -7.324 H2B3 TN4 47 
TN4 H2C1 1H2C H  0 0 N N N 20.510 34.590 16.258 -0.446 -1.091 -6.722 H2C1 TN4 48 
TN4 H2C2 2H2C H  0 0 N N N 18.755 34.752 15.875 -1.923 -1.977 -7.168 H2C2 TN4 49 
TN4 H2C3 3H2C H  0 0 N N N 19.216 33.923 17.324 -1.266 -0.735 -8.261 H2C3 TN4 50 
TN4 H2A1 1H2A H  0 0 N N N 15.775 29.874 15.532 1.591  -1.108 -4.268 H2A1 TN4 51 
TN4 H2A2 2H2A H  0 0 N N N 16.949 28.757 16.313 2.408  0.183  -3.356 H2A2 TN4 52 
TN4 H2A3 3H2A H  0 0 N N N 15.304 28.762 16.865 2.380  -1.477 -2.716 H2A3 TN4 53 
TN4 H441 1H44 H  0 0 N N N 15.070 32.899 23.674 -3.027 -0.405 5.287  H441 TN4 54 
TN4 H442 2H44 H  0 0 N N N 13.394 33.086 23.634 -2.625 1.323  5.422  H442 TN4 55 
# 
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 
TN4 N42 C41  SING N N 1  
TN4 N42 C43  SING N N 2  
TN4 N42 H42  SING N N 3  
TN4 C41 O4A  DOUB N N 4  
TN4 C41 O41  SING N N 5  
TN4 O41 C4   SING N N 6  
TN4 C4  C5   SING N N 7  
TN4 C4  C3   SING N N 8  
TN4 C4  H4   SING N N 9  
TN4 C5  C6   SING N N 10 
TN4 C5  H51  SING N N 11 
TN4 C5  H52  SING N N 12 
TN4 C6  C1   SING N N 13 
TN4 C6  H61  SING N N 14 
TN4 C6  H62  SING N N 15 
TN4 C1  O11  SING N N 16 
TN4 C1  C11  SING N N 17 
TN4 C1  C2   SING N N 18 
TN4 O11 C11  SING N N 19 
TN4 C11 H111 SING N N 20 
TN4 C11 H112 SING N N 21 
TN4 C2  C3   SING N N 22 
TN4 C2  C21  SING N N 23 
TN4 C2  H2   SING N N 24 
TN4 C3  O31  SING N N 25 
TN4 C3  H3   SING N N 26 
TN4 O31 C31  SING N N 27 
TN4 C31 H311 SING N N 28 
TN4 C31 H312 SING N N 29 
TN4 C31 H313 SING N N 30 
TN4 C21 O2A  SING N N 31 
TN4 C21 C22  SING N N 32 
TN4 C21 C2A  SING N N 33 
TN4 O2A C22  SING N N 34 
TN4 C22 C23  SING N N 35 
TN4 C22 H22  SING N N 36 
TN4 C23 C24  SING N N 37 
TN4 C23 H231 SING N N 38 
TN4 C23 H232 SING N N 39 
TN4 C24 C25  DOUB N N 40 
TN4 C24 H24  SING N N 41 
TN4 C25 C2B  SING N N 42 
TN4 C25 C2C  SING N N 43 
TN4 C2B H2B1 SING N N 44 
TN4 C2B H2B2 SING N N 45 
TN4 C2B H2B3 SING N N 46 
TN4 C2C H2C1 SING N N 47 
TN4 C2C H2C2 SING N N 48 
TN4 C2C H2C3 SING N N 49 
TN4 C2A H2A1 SING N N 50 
TN4 C2A H2A2 SING N N 51 
TN4 C2A H2A3 SING N N 52 
TN4 C43 O4B  DOUB N N 53 
TN4 C43 C44  SING N N 54 
TN4 C44 CL4  SING N N 55 
TN4 C44 H441 SING N N 56 
TN4 C44 H442 SING N N 57 
# 
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 
TN4 SMILES           ACDLabs              10.04 ClCC(=O)NC(=O)OC3CCC1(OC1)C(C2(OC2C/C=C(/C)C)C)C3OC                                                                                                                                   
TN4 InChI            InChI                1.02b InChI=1/C19H28ClNO6/c1-11(2)5-6-13-18(3,27-13)16-15(24-4)12(7-8-19(16)10-25-19)26-17(23)21-14(22)9-20/h5,12-13,15-16H,6-10H2,1-4H3,(H,21,22,23)/t12-,13-,15-,16-,18+,19+/m1/s1/f/h21H 
TN4 InChIKey         InChI                1.02b MSHZHSPISPJWHW-UVYVWKEADT                                                                                                                                                             
TN4 SMILES_CANONICAL CACTVS               3.341 CO[C@@H]1[C@@H](CC[C@]2(CO2)[C@H]1[C@@]3(C)O[C@@H]3CC=C(C)C)OC(=O)NC(=O)CCl                                                                                                           
TN4 SMILES           CACTVS               3.341 CO[CH]1[CH](CC[C]2(CO2)[CH]1[C]3(C)O[CH]3CC=C(C)C)OC(=O)NC(=O)CCl                                                                                                                     
TN4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)NC(=O)CCl)OC)C                                                                                                         
TN4 SMILES           "OpenEye OEToolkits" 1.5.0 CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)NC(=O)CCl)OC)C                                                                                                                                   
# 
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 
TN4 "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl (chloroacetyl)carbamate"        
TN4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3R,6R,7S,8S)-7-methoxy-8-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroethanoyl)carbamate" 
# 
