data_MXL
# 
_chem_comp.id                                    MXL 
_chem_comp.name                                  MOXALACTAM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H20 N6 O9 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "7-((CARBOXY(4-HYDROXYPHENYL)ACETYL)AMINO)-7-METHOXY-(3-((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-OXA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-10-30 
_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                        520.473 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MXL 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1K6R 
_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 
MXL O1   O1   O 0 1 N N N 3.972  13.752 61.336 1.147  1.931  -2.429 O1   MXL 1  
MXL C1   C1   C 0 1 N N N 3.977  14.289 62.442 0.803  1.979  -1.267 C1   MXL 2  
MXL C2   C2   C 0 1 N N R 2.836  15.220 63.009 1.418  2.541  0.005  C2   MXL 3  
MXL C3   C3   C 0 1 N N R 1.672  14.248 63.543 0.313  1.814  0.766  C3   MXL 4  
MXL N1   N1   N 0 1 N N N 1.740  12.878 63.035 -0.272 1.558  -0.589 N1   MXL 5  
MXL C4   C4   C 0 1 N N N 0.525  12.196 62.769 -1.597 1.116  -0.798 C4   MXL 6  
MXL C5   C5   C 0 1 N N N -0.708 12.767 62.966 -2.369 1.283  0.297  C5   MXL 7  
MXL C6   C6   C 0 1 N N N -0.761 14.173 63.489 -1.834 1.852  1.574  C6   MXL 8  
MXL O2   O2   O 0 1 N N N 0.435  14.935 63.210 -0.648 2.628  1.446  O2   MXL 9  
MXL C7   C7   C 0 1 N N N 0.635  10.811 62.261 -2.081 0.538  -2.065 C7   MXL 10 
MXL O3   O3   O 0 1 N N N 1.035  10.591 61.098 -3.204 0.080  -2.134 O3   MXL 11 
MXL O4   O4   O 0 1 N N N 0.331  9.853  63.003 -1.278 0.519  -3.147 O4   MXL 12 
MXL C8   C8   C 0 1 N N N -1.989 12.096 62.702 -3.820 0.883  0.231  C8   MXL 13 
MXL O5   O5   O 0 1 N N N 3.138  15.917 64.236 1.337  3.965  0.099  O5   MXL 14 
MXL C9   C9   C 0 1 N N N 4.434  16.456 64.444 2.406  4.492  -0.689 C9   MXL 15 
MXL N2   N2   N 0 1 N N N 2.327  16.105 61.949 2.760  2.027  0.285  N2   MXL 16 
MXL C10  C10  C 0 1 N N N 3.098  16.952 61.164 3.049  0.732  0.049  C10  MXL 17 
MXL O6   O6   O 0 1 N N N 4.351  17.004 61.235 2.198  -0.008 -0.396 O6   MXL 18 
MXL C11  C11  C 0 1 N N R 2.368  17.839 60.150 4.431  0.203  0.338  C11  MXL 19 
MXL C12  C12  C 0 1 N N N 3.286  18.941 59.687 4.742  0.384  1.801  C12  MXL 20 
MXL O7   O7   O 0 1 N N N 4.044  18.742 58.709 5.926  -0.017 2.290  O7   MXL 21 
MXL O8   O8   O 0 1 N N N 3.317  20.040 60.285 3.926  0.891  2.534  O8   MXL 22 
MXL C13  C13  C 0 1 Y N N 1.064  18.373 60.707 4.491  -1.262 -0.011 C13  MXL 23 
MXL C14  C14  C 0 1 Y N N 1.030  19.292 61.757 5.387  -1.708 -0.965 C14  MXL 24 
MXL C15  C15  C 0 1 Y N N -0.188 19.776 62.258 5.443  -3.050 -1.287 C15  MXL 25 
MXL C16  C16  C 0 1 Y N N -1.388 19.334 61.705 4.601  -3.951 -0.652 C16  MXL 26 
MXL C17  C17  C 0 1 Y N N -1.378 18.421 60.659 3.703  -3.501 0.306  C17  MXL 27 
MXL C18  C18  C 0 1 Y N N -0.155 17.947 60.167 3.654  -2.158 0.628  C18  MXL 28 
MXL O9   O9   O 0 1 N N N -2.593 19.800 62.202 4.655  -5.272 -0.966 O9   MXL 29 
MXL S1   S1   S 0 1 N N N ?      ?      ?      -3.986 -0.862 0.680  S1   MXL 30 
MXL C19  C19  C 0 1 Y N N ?      ?      ?      -5.730 -1.054 0.523  C19  MXL 31 
MXL N3   N3   N 0 1 Y N N ?      ?      ?      -6.591 -0.124 0.170  N3   MXL 32 
MXL N4   N4   N 0 1 Y N N ?      ?      ?      -7.784 -0.597 0.155  N4   MXL 33 
MXL N5   N5   N 0 1 Y N N ?      ?      ?      -7.777 -1.842 0.490  N5   MXL 34 
MXL N6   N6   N 0 1 Y N N ?      ?      ?      -6.437 -2.189 0.737  N6   MXL 35 
MXL C20  C20  C 0 1 N N N ?      ?      ?      -5.919 -3.496 1.148  C20  MXL 36 
MXL H31  1H3  H 0 1 N N N 1.768  14.080 64.626 0.635  0.937  1.327  H31  MXL 37 
MXL H61  1H6  H 0 1 N N N -1.612 14.684 63.014 -1.632 1.028  2.258  H61  MXL 38 
MXL H62  2H6  H 0 1 N N N -0.861 14.111 64.583 -2.607 2.479  2.020  H62  MXL 39 
MXL HO41 1HO4 H 0 0 N N N 0.460  9.036  62.535 -1.596 0.140  -3.978 HO41 MXL 40 
MXL H81  1H8  H 0 1 N N N -2.087 11.170 63.288 -4.397 1.493  0.926  H81  MXL 41 
MXL H82  2H8  H 0 1 N N N -2.856 12.709 62.989 -4.193 1.035  -0.782 H82  MXL 42 
MXL H91  1H9  H 0 1 N N N 4.934  16.595 63.474 3.358  4.132  -0.298 H91  MXL 43 
MXL H92  2H9  H 0 1 N N N 4.350  17.426 64.956 2.291  4.166  -1.722 H92  MXL 44 
MXL H93  3H9  H 0 1 N N N 5.023  15.764 65.064 2.385  5.581  -0.647 H93  MXL 45 
MXL HN21 1HN2 H 0 0 N N N 1.342  16.096 61.780 3.442  2.619  0.641  HN21 MXL 46 
MXL H111 1H11 H 0 0 N N N 2.096  17.228 59.276 5.161  0.749  -0.260 H111 MXL 47 
MXL HO71 1HO7 H 0 0 N N N 4.572  19.517 58.554 6.126  0.099  3.229  HO71 MXL 48 
MXL H141 1H14 H 0 0 N N N 1.957  19.636 62.191 6.042  -1.006 -1.460 H141 MXL 49 
MXL H151 1H15 H 0 0 N N N -0.195 20.489 63.069 6.143  -3.398 -2.033 H151 MXL 50 
MXL H171 1H17 H 0 0 N N N -2.307 18.079 60.228 3.046  -4.200 0.801  H171 MXL 51 
MXL H181 1H18 H 0 0 N N N -0.153 17.237 59.353 2.956  -1.807 1.373  H181 MXL 52 
MXL HO91 1HO9 H 0 0 N N N -2.528 19.907 63.144 5.303  -5.674 -0.372 HO91 MXL 53 
MXL H201 1H20 H 0 0 N N N ?      ?      ?      -5.677 -4.085 0.263  H201 MXL 54 
MXL H202 2H20 H 0 0 N N N ?      ?      ?      -5.020 -3.358 1.749  H202 MXL 55 
MXL H203 3H20 H 0 0 N N N ?      ?      ?      -6.673 -4.018 1.737  H203 MXL 56 
# 
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 
MXL O1  C1   DOUB N N 1  
MXL C1  C2   SING N N 2  
MXL C1  N1   SING N N 3  
MXL C2  C3   SING N N 4  
MXL C2  O5   SING N N 5  
MXL C2  N2   SING N N 6  
MXL C3  N1   SING N N 7  
MXL C3  O2   SING N N 8  
MXL C3  H31  SING N N 9  
MXL N1  C4   SING N N 10 
MXL C4  C5   DOUB N N 11 
MXL C4  C7   SING N N 12 
MXL C5  C6   SING N N 13 
MXL C5  C8   SING N N 14 
MXL C6  O2   SING N N 15 
MXL C6  H61  SING N N 16 
MXL C6  H62  SING N N 17 
MXL C7  O3   DOUB N N 18 
MXL C7  O4   SING N N 19 
MXL O4  HO41 SING N N 20 
MXL C8  S1   SING N N 21 
MXL C8  H81  SING N N 22 
MXL C8  H82  SING N N 23 
MXL O5  C9   SING N N 24 
MXL C9  H91  SING N N 25 
MXL C9  H92  SING N N 26 
MXL C9  H93  SING N N 27 
MXL N2  C10  SING N N 28 
MXL N2  HN21 SING N N 29 
MXL C10 O6   DOUB N N 30 
MXL C10 C11  SING N N 31 
MXL C11 C12  SING N N 32 
MXL C11 C13  SING N N 33 
MXL C11 H111 SING N N 34 
MXL C12 O7   SING N N 35 
MXL C12 O8   DOUB N N 36 
MXL O7  HO71 SING N N 37 
MXL C13 C14  DOUB Y N 38 
MXL C13 C18  SING Y N 39 
MXL C14 C15  SING Y N 40 
MXL C14 H141 SING N N 41 
MXL C15 C16  DOUB Y N 42 
MXL C15 H151 SING N N 43 
MXL C16 C17  SING Y N 44 
MXL C16 O9   SING N N 45 
MXL C17 C18  DOUB Y N 46 
MXL C17 H171 SING N N 47 
MXL C18 H181 SING N N 48 
MXL O9  HO91 SING N N 49 
MXL S1  C19  SING N N 50 
MXL C19 N3   DOUB Y N 51 
MXL C19 N6   SING Y N 52 
MXL N3  N4   SING Y N 53 
MXL N4  N5   DOUB Y N 54 
MXL N5  N6   SING Y N 55 
MXL N6  C20  SING N N 56 
MXL C20 H201 SING N N 57 
MXL C20 H202 SING N N 58 
MXL C20 H203 SING N N 59 
# 
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 
MXL SMILES           ACDLabs              10.04 O=C2N1C(=C(COC1C2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O 
MXL InChI            InChI                1.02b 
InChI=1/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12-,18-,20+/m1/s1/f/h21,29,31H 
MXL InChIKey         InChI                1.02b JWCSIUVGFCSJCK-LYGBFEHNDV 
MXL SMILES_CANONICAL CACTVS               3.341 CO[C@]1(NC(=O)[C@H](C(O)=O)c2ccc(O)cc2)[C@H]3OCC(=C(N3C1=O)C(O)=O)CSc4nnnn4C 
MXL SMILES           CACTVS               3.341 CO[C]1(NC(=O)[CH](C(O)=O)c2ccc(O)cc2)[CH]3OCC(=C(N3C1=O)C(O)=O)CSc4nnnn4C 
MXL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1c(nnn1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)[C@@H](c4ccc(cc4)O)C(=O)O)OC)OC2)C(=O)O 
MXL SMILES           "OpenEye OEToolkits" 1.5.0 Cn1c(nnn1)SCC2=C(N3C(C(C3=O)(NC(=O)C(c4ccc(cc4)O)C(=O)O)OC)OC2)C(=O)O 
# 
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 
MXL "SYSTEMATIC NAME" ACDLabs              10.04 "(6R,7R)-7-{[(2R)-2-carboxy-2-(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid"              
MXL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6R,7R)-7-[[(2R)-3-hydroxy-2-(4-hydroxyphenyl)-3-oxo-propanoyl]amino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" 
# 
