data_AZR
# 
_chem_comp.id                                    AZR 
_chem_comp.name                                  AZTREONAM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H17 N5 O8 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-09-12 
_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                        435.433 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AZR 
_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        1FR6 
_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 
AZR C7   C7   C 0 1 N N N 61.778 37.760 9.858  3.349  -1.488 -2.525 C7   AZR 1  
AZR S8   S8   S 0 1 Y N N 58.707 44.669 6.049  -1.160 4.545  0.193  S8   AZR 2  
AZR O9   O9   O 0 1 N N N 63.972 41.801 9.651  2.103  -1.857 1.617  O9   AZR 3  
AZR O10  O10  O 0 1 N N N 59.480 40.375 8.705  -1.112 -1.489 -0.695 O10  AZR 4  
AZR O11  O11  O 0 1 N N N 61.819 39.439 6.506  -3.392 -0.963 -0.042 O11  AZR 5  
AZR N12  N12  N 0 1 N N N 63.622 38.673 11.262 3.515  -0.969 -0.069 N12  AZR 6  
AZR N13  N13  N 0 1 N N N 61.755 40.696 8.634  0.568  -0.046 -0.542 N13  AZR 7  
AZR N14  N14  N 0 1 N N N 60.921 40.219 5.813  -2.993 0.396  -0.033 N14  AZR 8  
AZR N15  N15  N 0 1 Y N N 59.823 42.806 4.905  -0.010 2.429  -0.100 N15  AZR 9  
AZR N16  N16  N 0 1 N N N 59.242 44.539 3.409  1.680  4.191  -0.015 N16  AZR 10 
AZR S17  S17  S 0 1 N N N 65.198 38.242 10.913 5.078  -0.863 0.466  S17  AZR 11 
AZR C18  C18  C 0 1 N N S 62.652 38.924 10.154 2.876  -0.626 -1.353 C18  AZR 12 
AZR C19  C19  C 0 1 N N S 62.106 40.358 10.048 1.560  -1.109 -0.722 C19  AZR 13 
AZR C20  C20  C 0 1 N N N 63.201 41.333 10.480 2.370  -1.407 0.523  C20  AZR 14 
AZR C21  C21  C 0 1 N N N 60.492 40.692 8.092  -0.744 -0.349 -0.492 C21  AZR 15 
AZR C22  C22  C 0 1 N N N 60.347 41.083 6.629  -1.738 0.708  -0.189 C22  AZR 16 
AZR C23  C23  C 0 1 N N N 62.175 38.200 5.940  -4.808 -0.979 0.149  C23  AZR 17 
AZR C24  C24  C 0 1 Y N N 59.779 42.404 6.234  -1.304 2.116  -0.062 C24  AZR 18 
AZR C25  C25  C 0 1 Y N N 59.184 43.342 7.013  -2.228 3.113  0.102  C25  AZR 19 
AZR C26  C26  C 0 1 Y N N 59.308 43.966 4.654  0.393  3.681  0.006  C26  AZR 20 
AZR C27  C27  C 0 1 N N N 62.071 38.257 4.425  -5.150 -0.321 1.487  C27  AZR 21 
AZR C28  C28  C 0 1 N N N 63.666 37.998 6.140  -5.484 -0.208 -0.987 C28  AZR 22 
AZR C29  C29  C 0 1 N N N 61.270 37.118 6.553  -5.298 -2.404 0.150  C29  AZR 23 
AZR O30  O30  O 0 1 N N N 61.647 36.360 7.465  -6.605 -2.664 0.314  O30  AZR 24 
AZR O31  O31  O 0 1 N N N 60.101 36.975 6.131  -4.515 -3.312 0.003  O31  AZR 25 
AZR O32  O32  O 0 1 N N N 66.163 38.514 12.055 4.999  -0.828 1.884  O32  AZR 26 
AZR O33  O33  O 0 1 N N N 65.689 39.036 9.632  5.699  0.123  -0.348 O33  AZR 27 
AZR O34  O34  O 0 1 N N N 65.116 36.718 10.507 5.767  -2.176 0.123  O34  AZR 28 
AZR H71  1H7  H 0 1 N N N 61.054 37.947 9.031  2.607  -1.456 -3.322 H71  AZR 29 
AZR H72  2H7  H 0 1 N N N 62.388 36.850 9.650  4.299  -1.105 -2.897 H72  AZR 30 
AZR H73  3H7  H 0 1 N N N 61.247 37.420 10.778 3.478  -2.517 -2.190 H73  AZR 31 
AZR H13  H13  H 0 1 N N N 62.466 40.962 7.953  0.856  0.877  -0.459 H13  AZR 32 
AZR H161 1H16 H 0 0 N N N 59.608 44.110 2.558  1.826  5.145  0.079  H161 AZR 33 
AZR H162 2H16 H 0 0 N N N 59.667 45.463 3.483  2.437  3.594  -0.125 H162 AZR 34 
AZR H18  H18  H 0 1 N N N 63.239 38.962 9.207  2.889  0.440  -1.577 H18  AZR 35 
AZR H19  H19  H 0 1 N N N 61.198 40.432 10.691 1.146  -1.998 -1.198 H19  AZR 36 
AZR H25  H25  H 0 1 N N N 59.111 43.102 8.087  -3.304 3.053  0.159  H25  AZR 37 
AZR H271 1H27 H 0 0 N N N 62.352 37.275 3.976  -4.795 0.710  1.486  H271 AZR 38 
AZR H272 2H27 H 0 0 N N N 61.060 38.590 4.091  -6.230 -0.333 1.632  H272 AZR 39 
AZR H273 3H27 H 0 0 N N N 62.671 39.094 3.999  -4.668 -0.870 2.296  H273 AZR 40 
AZR H281 1H28 H 0 0 N N N 63.947 37.016 5.691  -5.240 -0.677 -1.940 H281 AZR 41 
AZR H282 2H28 H 0 0 N N N 64.272 38.843 5.739  -6.564 -0.220 -0.841 H282 AZR 42 
AZR H283 3H28 H 0 0 N N N 63.972 38.086 7.208  -5.129 0.823  -0.988 H283 AZR 43 
AZR H30  H30  H 0 1 N N N 61.088 35.691 7.843  -6.919 -3.578 0.315  H30  AZR 44 
AZR H34  H34  H 0 1 N N N 66.012 36.472 10.308 6.678  -2.105 0.439  H34  AZR 45 
# 
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 
AZR C7  C18  SING N N 1  
AZR C7  H71  SING N N 2  
AZR C7  H72  SING N N 3  
AZR C7  H73  SING N N 4  
AZR S8  C25  SING Y N 5  
AZR S8  C26  SING Y N 6  
AZR O9  C20  DOUB N N 7  
AZR O10 C21  DOUB N N 8  
AZR O11 N14  SING N N 9  
AZR O11 C23  SING N N 10 
AZR N12 S17  SING N N 11 
AZR N12 C18  SING N N 12 
AZR N12 C20  SING N N 13 
AZR N13 C19  SING N N 14 
AZR N13 C21  SING N N 15 
AZR N13 H13  SING N N 16 
AZR N14 C22  DOUB N Z 17 
AZR N15 C24  SING Y N 18 
AZR N15 C26  DOUB Y N 19 
AZR N16 C26  SING N N 20 
AZR N16 H161 SING N N 21 
AZR N16 H162 SING N N 22 
AZR S17 O32  DOUB N N 23 
AZR S17 O33  DOUB N N 24 
AZR S17 O34  SING N N 25 
AZR C18 C19  SING N N 26 
AZR C18 H18  SING N N 27 
AZR C19 C20  SING N N 28 
AZR C19 H19  SING N N 29 
AZR C21 C22  SING N N 30 
AZR C22 C24  SING N N 31 
AZR C23 C27  SING N N 32 
AZR C23 C28  SING N N 33 
AZR C23 C29  SING N N 34 
AZR C24 C25  DOUB Y N 35 
AZR C25 H25  SING N N 36 
AZR C27 H271 SING N N 37 
AZR C27 H272 SING N N 38 
AZR C27 H273 SING N N 39 
AZR C28 H281 SING N N 40 
AZR C28 H282 SING N N 41 
AZR C28 H283 SING N N 42 
AZR C29 O30  SING N N 43 
AZR C29 O31  DOUB N N 44 
AZR O30 H30  SING N N 45 
AZR O34 H34  SING N N 46 
# 
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 
AZR SMILES           ACDLabs              10.04 O=S(=O)(O)N2C(=O)C(NC(=O)C(=N\OC(C(=O)O)(C)C)/c1nc(sc1)N)C2C                                                                                                                                      
AZR InChI            InChI                1.02b InChI=1/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1/f/h16,21,23H,14H2 
AZR InChIKey         InChI                1.02b WZPBZJONDBGPKJ-PSZCVDLGDL                                                                                                                                                                         
AZR SMILES_CANONICAL CACTVS               3.341 C[C@H]1[C@H](NC(=O)\C(=N/OC(C)(C)C(O)=O)c2csc(N)n2)C(=O)N1[S](O)(=O)=O                                                                                                                            
AZR SMILES           CACTVS               3.341 C[CH]1[CH](NC(=O)C(=NOC(C)(C)C(O)=O)c2csc(N)n2)C(=O)N1[S](O)(=O)=O                                                                                                                                
AZR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)c2csc(n2)N                                                                                                                               
AZR SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)c2csc(n2)N                                                                                                                                        
# 
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 
AZR "SYSTEMATIC NAME" ACDLabs              10.04 "2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl)-2-{[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino}-2-oxoethylidene]amino}oxy)-2-methylpropanoic acid" 
AZR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-azetidin-3-yl]amino]-2-oxo-ethylidene]amino]oxy-2-methyl-propanoic acid"     
# 
