data_FXM
# 
_chem_comp.id                                    FXM 
_chem_comp.name                                  "2,2-DIMETHYLPROPANOYLOXYMETHYL (6R,7R)-7-[(Z)-2-(2-AMINOTHIAZOL-4-YL)PENT-2-ENYLAMINO]-3-CARBAMOYLOXYMETHYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H29 N5 O8 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FLOMOX 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-11-16 
_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                        567.635 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FXM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "not provided" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   Y 
_chem_comp.pdbx_model_coordinates_db_code        2EXB 
_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 
FXM C31  C31  C 0 1 N N N 86.066 -9.965  38.263 ? ? ? C31  FXM 1  
FXM C30  C30  C 0 1 N N N 85.895 -8.441  38.263 ? ? ? C30  FXM 2  
FXM C32  C32  C 0 1 N N N 84.793 -8.038  39.263 ? ? ? C32  FXM 3  
FXM C33  C33  C 0 1 N N N 85.481 -7.966  36.848 ? ? ? C33  FXM 4  
FXM C27  C27  C 0 1 N N N 87.261 -7.807  38.680 ? ? ? C27  FXM 5  
FXM O29  O29  O 0 1 N N N 87.922 -7.131  37.884 ? ? ? O29  FXM 6  
FXM O28  O28  O 0 1 N N N 87.776 -7.993  39.939 ? ? ? O28  FXM 7  
FXM C26  C26  C 0 1 N N N 88.211 -6.707  40.511 ? ? ? C26  FXM 8  
FXM O9   O9   O 0 1 N N N 87.138 -6.032  41.228 ? ? ? O9   FXM 9  
FXM C8   C8   C 0 1 N N N 86.734 -4.878  40.628 ? ? ? C8   FXM 10 
FXM O10  O10  O 0 1 N N N 85.762 -4.899  39.880 ? ? ? O10  FXM 11 
FXM C2   C2   C 0 1 N N N 87.100 -3.569  41.315 ? ? ? C2   FXM 12 
FXM N3   N3   N 0 1 N N N 86.408 -3.236  42.434 ? ? ? N3   FXM 13 
FXM C1   C1   C 0 1 N N N 87.974 -2.690  40.656 ? ? ? C1   FXM 14 
FXM C16  C16  C 0 1 N N N 89.078 -3.312  39.781 ? ? ? C16  FXM 15 
FXM O17  O17  O 0 1 N N N 90.249 -3.729  40.346 ? ? ? O17  FXM 16 
FXM C18  C18  C 0 1 N N N 91.320 -2.873  39.847 ? ? ? C18  FXM 17 
FXM O20  O20  O 0 1 N N N 91.928 -3.468  38.676 ? ? ? O20  FXM 18 
FXM N19  N19  N 0 1 N N N 92.325 -2.454  40.859 ? ? ? N19  FXM 19 
FXM C6   C6   C 0 1 N N N 88.254 -1.277  41.177 ? ? ? C6   FXM 20 
FXM S5   S5   S 0 1 N N N 88.481 -1.462  42.973 ? ? ? S5   FXM 21 
FXM C4   C4   C 0 1 N N R 86.809 -2.135  43.343 ? ? ? C4   FXM 22 
FXM C7   C7   C 0 1 N N R 86.555 -2.428  44.838 ? ? ? C7   FXM 23 
FXM C11  C11  C 0 1 N N N 85.225 -3.210  45.063 ? ? ? C11  FXM 24 
FXM O12  O12  O 0 1 N N N 85.157 -4.296  45.653 ? ? ? O12  FXM 25 
FXM N14  N14  N 0 1 N N N 87.709 -3.037  45.546 ? ? ? N14  FXM 26 
FXM C13  C13  C 0 1 N N N 87.569 -3.303  46.858 ? ? ? C13  FXM 27 
FXM O15  O15  O 0 1 N N N 86.516 -3.065  47.462 ? ? ? O15  FXM 28 
FXM C34  C34  C 0 1 N N N 88.739 -3.959  47.649 ? ? ? C34  FXM 29 
FXM C35  C35  C 0 1 N N N 88.521 -4.217  49.013 ? ? ? C35  FXM 30 
FXM C36  C36  C 0 1 N N N 87.335 -3.943  49.699 ? ? ? C36  FXM 31 
FXM C37  C37  C 0 1 N N N 87.138 -4.716  50.991 ? ? ? C37  FXM 32 
FXM C21  C21  C 0 1 Y N N 89.998 -4.258  47.129 ? ? ? C21  FXM 33 
FXM N22  N22  N 0 1 Y N N 90.423 -4.072  45.845 ? ? ? N22  FXM 34 
FXM C25  C25  C 0 1 Y N N 90.953 -4.737  47.968 ? ? ? C25  FXM 35 
FXM S24  S24  S 0 1 Y N N 92.387 -4.987  47.096 ? ? ? S24  FXM 36 
FXM C23  C23  C 0 1 Y N N 91.719 -4.427  45.619 ? ? ? C23  FXM 37 
FXM N38  N38  N 0 1 N N N 92.393 -4.343  44.455 ? ? ? N38  FXM 38 
FXM H311 1H31 H 0 0 N N N 85.214 -10.429 38.781 ? ? ? H311 FXM 39 
FXM H312 2H31 H 0 0 N N N 86.999 -10.229 38.782 ? ? ? H312 FXM 40 
FXM H313 3H31 H 0 0 N N N 86.107 -10.330 37.226 ? ? ? H313 FXM 41 
FXM H321 1H32 H 0 0 N N N 84.009 -8.809  39.275 ? ? ? H321 FXM 42 
FXM H322 2H32 H 0 0 N N N 84.356 -7.075  38.959 ? ? ? H322 FXM 43 
FXM H323 3H32 H 0 0 N N N 85.227 -7.942  40.269 ? ? ? H323 FXM 44 
FXM H331 1H33 H 0 0 N N N 84.517 -8.422  36.576 ? ? ? H331 FXM 45 
FXM H332 2H33 H 0 0 N N N 86.249 -8.269  36.121 ? ? ? H332 FXM 46 
FXM H333 3H33 H 0 0 N N N 85.383 -6.870  36.843 ? ? ? H333 FXM 47 
FXM H261 1H26 H 0 0 N N N 88.526 -6.057  39.682 ? ? ? H261 FXM 48 
FXM H262 2H26 H 0 0 N N N 89.036 -6.897  41.213 ? ? ? H262 FXM 49 
FXM H161 1H16 H 0 0 N N N 89.388 -2.482  39.129 ? ? ? H161 FXM 50 
FXM H162 2H16 H 0 0 N N N 88.631 -4.203  39.315 ? ? ? H162 FXM 51 
FXM H191 1H19 H 0 0 N N N 92.336 -2.698  41.829 ? ? ? H191 FXM 52 
FXM H192 2H19 H 0 0 N N N 92.988 -1.880  40.378 ? ? ? H192 FXM 53 
FXM H61  1H6  H 0 1 N N N 87.433 -0.585  40.939 ? ? ? H61  FXM 54 
FXM H62  2H6  H 0 1 N N N 89.157 -0.859  40.709 ? ? ? H62  FXM 55 
FXM H4   H4   H 0 1 N N N 86.118 -1.309  43.119 ? ? ? H4   FXM 56 
FXM H7   H7   H 0 1 N N N 86.434 -1.442  45.311 ? ? ? H7   FXM 57 
FXM H14  H14  H 0 1 N N N 88.561 -3.243  45.065 ? ? ? H14  FXM 58 
FXM H35  H35  H 0 1 N N N 89.331 -4.660  49.573 ? ? ? H35  FXM 59 
FXM H361 1H36 H 0 0 N N N 86.516 -4.248  49.031 ? ? ? H361 FXM 60 
FXM H362 2H36 H 0 0 N N N 87.337 -2.872  49.950 ? ? ? H362 FXM 61 
FXM H371 1H37 H 0 0 N N N 86.200 -4.398  51.469 ? ? ? H371 FXM 62 
FXM H372 2H37 H 0 0 N N N 87.981 -4.517  51.669 ? ? ? H372 FXM 63 
FXM H373 3H37 H 0 0 N N N 87.090 -5.793  50.771 ? ? ? H373 FXM 64 
FXM H25  H25  H 0 1 N N N 90.821 -4.928  49.023 ? ? ? H25  FXM 65 
FXM H381 1H38 H 0 0 N N N 93.346 -4.592  44.280 ? ? ? H381 FXM 66 
FXM H382 2H38 H 0 0 N N N 91.728 -3.976  43.805 ? ? ? H382 FXM 67 
# 
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 
FXM C31 C30  SING N N 1  
FXM C31 H311 SING N N 2  
FXM C31 H312 SING N N 3  
FXM C31 H313 SING N N 4  
FXM C30 C32  SING N N 5  
FXM C30 C33  SING N N 6  
FXM C30 C27  SING N N 7  
FXM C32 H321 SING N N 8  
FXM C32 H322 SING N N 9  
FXM C32 H323 SING N N 10 
FXM C33 H331 SING N N 11 
FXM C33 H332 SING N N 12 
FXM C33 H333 SING N N 13 
FXM C27 O29  DOUB N N 14 
FXM C27 O28  SING N N 15 
FXM O28 C26  SING N N 16 
FXM C26 O9   SING N N 17 
FXM C26 H261 SING N N 18 
FXM C26 H262 SING N N 19 
FXM O9  C8   SING N N 20 
FXM C8  O10  DOUB N N 21 
FXM C8  C2   SING N N 22 
FXM C2  N3   SING N N 23 
FXM C2  C1   DOUB N N 24 
FXM N3  C4   SING N N 25 
FXM N3  C11  SING N N 26 
FXM C1  C16  SING N N 27 
FXM C1  C6   SING N N 28 
FXM C16 O17  SING N N 29 
FXM C16 H161 SING N N 30 
FXM C16 H162 SING N N 31 
FXM O17 C18  SING N N 32 
FXM C18 O20  DOUB N N 33 
FXM C18 N19  SING N N 34 
FXM N19 H191 SING N N 35 
FXM N19 H192 SING N N 36 
FXM C6  S5   SING N N 37 
FXM C6  H61  SING N N 38 
FXM C6  H62  SING N N 39 
FXM S5  C4   SING N N 40 
FXM C4  C7   SING N N 41 
FXM C4  H4   SING N N 42 
FXM C7  C11  SING N N 43 
FXM C7  N14  SING N N 44 
FXM C7  H7   SING N N 45 
FXM C11 O12  DOUB N N 46 
FXM N14 C13  SING N N 47 
FXM N14 H14  SING N N 48 
FXM C13 O15  DOUB N N 49 
FXM C13 C34  SING N N 50 
FXM C34 C35  DOUB N Z 51 
FXM C34 C21  SING N N 52 
FXM C35 C36  SING N N 53 
FXM C35 H35  SING N N 54 
FXM C36 C37  SING N N 55 
FXM C36 H361 SING N N 56 
FXM C36 H362 SING N N 57 
FXM C37 H371 SING N N 58 
FXM C37 H372 SING N N 59 
FXM C37 H373 SING N N 60 
FXM C21 N22  SING Y N 61 
FXM C21 C25  DOUB Y N 62 
FXM N22 C23  DOUB Y N 63 
FXM C25 S24  SING Y N 64 
FXM C25 H25  SING N N 65 
FXM S24 C23  SING Y N 66 
FXM C23 N38  SING N N 67 
FXM N38 H381 SING N N 68 
FXM N38 H382 SING N N 69 
# 
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 
FXM SMILES           ACDLabs              10.04 O=C2N1C(=C(CSC1C2NC(=O)C(=C/CC)\c3nc(sc3)N)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C 
FXM InChI            InChI                1.02b 
InChI=1/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,18-/m1/s1/f/h27H,24-25H2 
FXM InChIKey         InChI                1.02b WVPAABNYMHNFJG-GJIUGSEPDU 
FXM SMILES_CANONICAL CACTVS               3.341 CC\C=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C)COC(N)=O)c3csc(N)n3 
FXM SMILES           CACTVS               3.341 CCC=C(C(=O)N[CH]1[CH]2SCC(=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C)COC(N)=O)c3csc(N)n3 
FXM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC\C=C(\c1csc(n1)N)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C 
FXM SMILES           "OpenEye OEToolkits" 1.5.0 CCC=C(c1csc(n1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)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 
FXM "SYSTEMATIC NAME" ACDLabs              10.04 "[(2,2-dimethylpropanoyl)oxy]methyl (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino}-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate" 
FXM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2,2-dimethylpropanoyloxymethyl (6R,7R)-3-(aminocarbonyloxymethyl)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate"    
# 
