data_AIC
# 
_chem_comp.id                                    AIC 
_chem_comp.name                                  "(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H19 N3 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "AMPICILLIN; D(-)-ALPHA-AMINOBENZYLPENICILLIN; 6-[D(-)-ALPHA-AMINOPHENYLLACETAMIDO]PENICILLANIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-02-17 
_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                        349.405 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AIC 
_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        1H8S 
_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 
AIC C8   C8   C 0 1 Y N N 22.038 39.358 10.486 2.299  0.576  -4.598 C8   AIC 1  
AIC C5   C5   C 0 1 Y N N 21.478 38.652 12.770 0.071  0.546  -3.720 C5   AIC 2  
AIC C6   C6   C 0 1 N N N 15.486 36.115 10.473 1.611  0.110  2.614  C6   AIC 3  
AIC N1   N1   N 0 1 N N N 18.839 36.650 12.759 -0.794 -0.023 -0.637 N1   AIC 4  
AIC C2   C2   C 0 1 N N N 14.720 33.727 10.825 -0.176 0.482  4.332  C2   AIC 5  
AIC N3   N3   N 0 1 N N N 16.952 34.413 11.617 -0.701 -0.798 2.345  N3   AIC 6  
AIC C4   C4   C 0 1 N N R 20.506 38.219 13.765 -0.982 1.131  -2.816 C4   AIC 7  
AIC C1   C1   C 0 1 N N N 13.996 36.400 10.172 2.226  -0.812 3.668  C1   AIC 8  
AIC C3   C3   C 0 1 N N N 20.035 36.854 13.514 -1.426 0.089  -1.822 C3   AIC 9  
AIC C7   C7   C 0 1 Y N N 21.081 38.944 11.437 1.331  1.112  -3.769 C7   AIC 10 
AIC C9   C9   C 0 1 Y N N 23.385 39.503 10.871 2.006  -0.526 -5.378 C9   AIC 11 
AIC C10  C10  C 0 1 Y N N 23.769 39.251 12.209 0.746  -1.093 -5.329 C10  AIC 12 
AIC C11  C11  C 0 1 Y N N 22.827 38.790 13.146 -0.219 -0.559 -4.496 C11  AIC 13 
AIC C12  C12  C 0 1 N N S 15.876 34.606 10.549 0.092  0.323  2.858  C12  AIC 14 
AIC C13  C13  C 0 1 N N R 16.822 35.355 12.736 -0.098 -1.556 1.222  C13  AIC 15 
AIC C14  C14  C 0 1 N N R 18.326 35.336 12.802 -1.226 -1.036 0.328  C14  AIC 16 
AIC C15  C15  C 0 1 N N N 18.321 34.767 11.494 -1.828 -0.459 1.592  C15  AIC 17 
AIC C16  C16  C 0 1 N N N 16.351 36.801 9.418  2.360  1.442  2.535  C16  AIC 18 
AIC N2   N2   N 0 1 N N N 19.430 39.109 13.782 -2.133 1.562  -3.621 N2   AIC 19 
AIC O1   O1   O 0 1 N N N 14.559 33.250 11.975 -0.491 -0.477 4.996  O1   AIC 20 
AIC O2   O2   O 0 1 N N N 13.885 33.457 9.908  -0.067 1.689  4.908  O2   AIC 21 
AIC O3   O3   O 0 1 N N N 20.713 35.886 13.949 -2.352 -0.647 -2.088 O3   AIC 22 
AIC O4   O4   O 0 1 N N N 19.164 34.665 10.584 -2.884 0.075  1.855  O4   AIC 23 
AIC S1   S1   S 0 1 N N N 15.848 36.708 12.089 1.514  -0.713 0.962  S1   AIC 24 
AIC HC8  8HC  H 0 1 N N N 21.734 39.567 9.446  3.283  1.019  -4.636 HC8  AIC 25 
AIC HN1  1HN  H 0 1 N N N 18.383 37.390 12.226 -0.054 0.565  -0.424 HN1  AIC 26 
AIC HC4  4HC  H 0 1 N N N 21.008 38.215 14.760 -0.570 1.988  -2.284 HC4  AIC 27 
AIC HC1  1HC  H 0 1 N N N 13.717 37.478 10.117 3.270  -1.004 3.418  HC1  AIC 28 
AIC HC2  2HC  H 0 1 N N N 13.688 35.877 9.236  2.169  -0.336 4.646  HC2  AIC 29 
AIC HC3  3HC  H 0 1 N N N 13.348 35.874 10.912 1.679  -1.754 3.690  HC3  AIC 30 
AIC HC7  7HC  H 0 1 N N N 20.023 38.848 11.138 1.560  1.974  -3.159 HC7  AIC 31 
AIC HC9  9HC  H 0 1 N N N 24.137 39.813 10.126 2.761  -0.945 -6.026 HC9  AIC 32 
AIC HC01 1HC0 H 0 0 N N N 24.813 39.415 12.524 0.517  -1.954 -5.939 HC01 AIC 33 
AIC HC11 1HC1 H 0 0 N N N 23.144 38.537 14.171 -1.203 -1.002 -4.458 HC11 AIC 34 
AIC HC21 1HC2 H 0 0 N N N 16.268 34.311 9.547  -0.207 1.235  2.342  HC21 AIC 35 
AIC HC31 1HC3 H 0 0 N N N 16.323 35.260 13.728 -0.039 -2.638 1.337  HC31 AIC 36 
AIC HC41 1HC4 H 0 0 N N N 18.874 34.868 13.652 -1.826 -1.826 -0.122 HC41 AIC 37 
AIC H161 1H16 H 0 0 N N N 17.425 36.595 9.635  3.404  1.257  2.281  H161 AIC 38 
AIC H162 2H16 H 0 0 N N N 16.065 36.508 8.380  1.906  2.070  1.769  H162 AIC 39 
AIC H163 3H16 H 0 0 N N N 16.136 37.892 9.338  2.305  1.948  3.499  H163 AIC 40 
AIC HN21 1HN2 H 0 0 N N N 18.749 38.805 14.478 -2.480 0.740  -4.093 HN21 AIC 41 
AIC HN22 2HN2 H 0 0 N N N 19.011 39.225 12.859 -2.850 1.848  -2.971 HN22 AIC 42 
AIC HO2  2HO  H 0 1 N N N 13.142 32.892 10.085 -0.239 1.791  5.854  HO2  AIC 43 
# 
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 
AIC C8  C7   DOUB Y N 1  
AIC C8  C9   SING Y N 2  
AIC C8  HC8  SING N N 3  
AIC C5  C4   SING N N 4  
AIC C5  C7   SING Y N 5  
AIC C5  C11  DOUB Y N 6  
AIC C6  C1   SING N N 7  
AIC C6  C12  SING N N 8  
AIC C6  C16  SING N N 9  
AIC C6  S1   SING N N 10 
AIC N1  C3   SING N N 11 
AIC N1  C14  SING N N 12 
AIC N1  HN1  SING N N 13 
AIC C2  C12  SING N N 14 
AIC C2  O1   DOUB N N 15 
AIC C2  O2   SING N N 16 
AIC N3  C12  SING N N 17 
AIC N3  C13  SING N N 18 
AIC N3  C15  SING N N 19 
AIC C4  C3   SING N N 20 
AIC C4  N2   SING N N 21 
AIC C4  HC4  SING N N 22 
AIC C1  HC1  SING N N 23 
AIC C1  HC2  SING N N 24 
AIC C1  HC3  SING N N 25 
AIC C3  O3   DOUB N N 26 
AIC C7  HC7  SING N N 27 
AIC C9  C10  DOUB Y N 28 
AIC C9  HC9  SING N N 29 
AIC C10 C11  SING Y N 30 
AIC C10 HC01 SING N N 31 
AIC C11 HC11 SING N N 32 
AIC C12 HC21 SING N N 33 
AIC C13 C14  SING N N 34 
AIC C13 S1   SING N N 35 
AIC C13 HC31 SING N N 36 
AIC C14 C15  SING N N 37 
AIC C14 HC41 SING N N 38 
AIC C15 O4   DOUB N N 39 
AIC C16 H161 SING N N 40 
AIC C16 H162 SING N N 41 
AIC C16 H163 SING N N 42 
AIC N2  HN21 SING N N 43 
AIC N2  HN22 SING N N 44 
AIC O2  HO2  SING N N 45 
# 
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 
AIC SMILES           ACDLabs              10.04 O=C(O)C2N3C(=O)C(NC(=O)C(c1ccccc1)N)C3SC2(C)C                                                                                                                           
AIC InChI            InChI                1.02b InChI=1/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1/f/h18,22H 
AIC InChIKey         InChI                1.02b AVKUERGKIZMTKX-KXDAXDHGDU                                                                                                                                               
AIC SMILES_CANONICAL CACTVS               3.341 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O                                                                                                          
AIC SMILES           CACTVS               3.341 CC1(C)S[CH]2[CH](NC(=O)[CH](N)c3ccccc3)C(=O)N2[CH]1C(O)=O                                                                                                               
AIC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N)C(=O)O)C                                                                                                      
AIC SMILES           "OpenEye OEToolkits" 1.5.0 CC1(C(N2C(S1)C(C2=O)NC(=O)C(c3ccccc3)N)C(=O)O)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 
AIC "SYSTEMATIC NAME" ACDLabs              10.04 "(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid"    
AIC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid" 
# 
