data_LKM
# 
_chem_comp.id                                    LKM 
_chem_comp.name                                  "N-({6-[(4-CYANO-2-FLUOROBENZYL)OXY]NAPHTHALEN-2-YL}SULFONYL)-D-GLUTAMIC ACID" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             ? 
_chem_comp.formula                               "C23 H19 F N2 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-05-14 
_chem_comp.pdbx_modified_date                    2008-11-21 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        486.470 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LKM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2VTD 
_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 
LKM N31  N31  N 0 1 N N N -1.590 -11.216 -21.187 -1.590 -11.216 -21.187 N31  LKM 1  
LKM C30  C30  C 0 1 N N N -1.495 -12.355 -21.276 -1.495 -12.355 -21.276 C30  LKM 2  
LKM C27  C27  C 0 1 Y N N -1.416 -13.622 -21.469 -1.416 -13.622 -21.469 C27  LKM 3  
LKM C28  C28  C 0 1 Y N N -1.215 -14.550 -20.455 -1.215 -14.550 -20.455 C28  LKM 4  
LKM C29  C29  C 0 1 Y N N -1.150 -15.909 -20.767 -1.150 -15.909 -20.767 C29  LKM 5  
LKM C26  C26  C 0 1 Y N N -1.555 -14.070 -22.770 -1.555 -14.070 -22.770 C26  LKM 6  
LKM C25  C25  C 0 1 Y N N -1.489 -15.420 -23.072 -1.489 -15.420 -23.072 C25  LKM 7  
LKM C24  C24  C 0 1 Y N N -1.290 -16.325 -22.078 -1.290 -16.325 -22.078 C24  LKM 8  
LKM C23  C23  C 0 1 N N N -1.213 -17.763 -22.501 -1.213 -17.763 -22.501 C23  LKM 9  
LKM O22  O22  O 0 1 N N N -0.863 -18.511 -21.367 -0.863 -18.511 -21.367 O22  LKM 10 
LKM C20  C20  C 0 1 Y N N 0.310  -19.181 -21.153 0.310  -19.181 -21.153 C20  LKM 11 
LKM C19  C19  C 0 1 Y N N 1.315  -19.464 -22.071 1.315  -19.464 -22.071 C19  LKM 12 
LKM C18  C18  C 0 1 Y N N 2.447  -20.169 -21.645 2.447  -20.169 -21.645 C18  LKM 13 
LKM C21  C21  C 0 1 Y N N 0.430  -19.610 -19.872 0.430  -19.610 -19.872 C21  LKM 14 
LKM C15  C15  C 0 1 Y N N 1.519  -20.302 -19.460 1.519  -20.302 -19.460 C15  LKM 15 
LKM C16  C16  C 0 1 Y N N 2.546  -20.590 -20.325 2.546  -20.590 -20.325 C16  LKM 16 
LKM C17  C17  C 0 1 Y N N 3.626  -21.303 -19.834 3.626  -21.303 -19.834 C17  LKM 17 
LKM C14  C14  C 0 1 Y N N 1.531  -20.673 -18.143 1.531  -20.673 -18.143 C14  LKM 18 
LKM C13  C13  C 0 1 Y N N 2.595  -21.377 -17.669 2.595  -21.377 -17.669 C13  LKM 19 
LKM C12  C12  C 0 1 Y N N 3.639  -21.682 -18.506 3.639  -21.682 -18.506 C12  LKM 20 
LKM S11  S11  S 0 1 N N N 4.791  -22.528 -17.870 4.791  -22.528 -17.870 S11  LKM 21 
LKM O33  O33  O 0 1 N N N 5.987  -22.396 -18.683 5.987  -22.396 -18.683 O33  LKM 22 
LKM O32  O32  O 0 1 N N N 5.019  -22.195 -16.480 5.019  -22.195 -16.480 O32  LKM 23 
LKM N    N    N 0 1 N N N 4.267  -23.947 -17.843 4.267  -23.947 -17.843 N    LKM 24 
LKM CA   CA   C 0 1 N N R 4.037  -24.701 -19.073 4.037  -24.701 -19.073 CA   LKM 25 
LKM C    C    C 0 1 N N N 5.289  -25.368 -19.569 5.289  -25.368 -19.569 C    LKM 26 
LKM O    O    O 0 1 N N N 5.482  -25.402 -20.790 5.482  -25.402 -20.790 O    LKM 27 
LKM OXT  OXT  O 0 1 N N N 6.063  -25.858 -18.748 6.063  -25.858 -18.748 OXT  LKM 28 
LKM CB   CB   C 0 1 N N N 2.937  -25.734 -18.793 2.937  -25.734 -18.793 CB   LKM 29 
LKM CG   CG   C 0 1 N N N 2.517  -26.418 -20.078 2.517  -26.418 -20.078 CG   LKM 30 
LKM CD   CD   C 0 1 N N N 1.307  -27.316 -19.984 1.307  -27.316 -19.984 CD   LKM 31 
LKM OE1  OE1  O 0 1 N N N 1.158  -28.128 -20.902 1.158  -28.128 -20.902 OE1  LKM 32 
LKM OE2  OE2  O 0 1 N N N 0.526  -27.233 -19.036 0.526  -27.233 -19.036 OE2  LKM 33 
LKM F2   F2   F 0 1 N N N -1.617 -15.871 -24.324 -1.617 -15.871 -24.324 F2   LKM 34 
LKM H28  H28  H 0 1 N N N -1.110 -14.222 -19.431 -1.110 -14.222 -19.431 H28  LKM 35 
LKM H26  H26  H 0 1 N N N -1.718 -13.355 -23.563 -1.718 -13.356 -23.563 H26  LKM 36 
LKM H29  H29  H 0 1 N N N -0.990 -16.636 -19.984 -0.990 -16.636 -19.984 H29  LKM 37 
LKM H231 1H23 H 0 0 N N N -2.185 -18.097 -22.892 -2.185 -18.097 -22.892 H231 LKM 38 
LKM H232 2H23 H 0 0 N N N -0.468 -17.895 -23.299 -0.468 -17.895 -23.299 H232 LKM 39 
LKM H19  H19  H 0 1 N N N 1.224  -19.144 -23.099 1.224  -19.144 -23.099 H19  LKM 40 
LKM H21  H21  H 0 1 N N N -0.359 -19.395 -19.166 -0.359 -19.396 -19.166 H21  LKM 41 
LKM H18  H18  H 0 1 N N N 3.243  -20.385 -22.342 3.243  -20.385 -22.342 H18  LKM 42 
LKM H14  H14  H 0 1 N N N 0.711  -20.412 -17.491 0.711  -20.412 -17.491 H14  LKM 43 
LKM H17  H17  H 0 1 N N N 4.450  -21.560 -20.483 4.450  -21.560 -20.483 H17  LKM 44 
LKM H13  H13  H 0 1 N N N 2.618  -21.695 -16.637 2.618  -21.695 -16.637 H13  LKM 45 
LKM H    H    H 0 1 N N N 4.942  -24.474 -17.327 4.942  -24.474 -17.327 H    LKM 46 
LKM HA   HA   H 0 1 N N N 3.723  -24.011 -19.870 3.723  -24.011 -19.870 HA   LKM 47 
LKM HBC1 1HBC H 0 0 N N N 3.320  -26.489 -18.091 3.320  -26.489 -18.090 HBC1 LKM 48 
LKM HBC2 2HBC H 0 0 N N N 2.066  -25.221 -18.360 2.066  -25.221 -18.360 HBC2 LKM 49 
LKM HB   HB   H 0 1 N N N 6.298  -25.854 -20.970 6.298  -25.854 -20.970 HB   LKM 50 
LKM HGC1 1HGC H 0 0 N N N 2.284  -25.629 -20.809 2.284  -25.629 -20.809 HGC1 LKM 51 
LKM HGC2 2HGC H 0 0 N N N 3.356  -27.072 -20.359 3.356  -27.072 -20.359 HGC2 LKM 52 
LKM HE1  HE1  H 0 1 N N N 0.375  -28.643 -20.746 0.375  -28.643 -20.746 HE1  LKM 53 
# 
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 
LKM N31 C30  TRIP N N 1  
LKM C30 C27  SING N N 2  
LKM C27 C28  SING Y N 3  
LKM C27 C26  DOUB Y N 4  
LKM C28 C29  DOUB Y N 5  
LKM C29 C24  SING N N 6  
LKM C26 C25  SING Y N 7  
LKM C25 C24  DOUB N N 8  
LKM C25 F2   SING Y N 9  
LKM C24 C23  SING N N 10 
LKM C23 O22  SING Y N 11 
LKM O22 C20  SING N N 12 
LKM C20 C19  SING N N 13 
LKM C20 C21  DOUB N N 14 
LKM C19 C18  DOUB N N 15 
LKM C18 C16  SING N N 16 
LKM C21 C15  SING N N 17 
LKM C15 C16  DOUB Y N 18 
LKM C15 C14  SING Y N 19 
LKM C16 C17  SING Y N 20 
LKM C17 C12  DOUB N N 21 
LKM C14 C13  DOUB Y N 22 
LKM C13 C12  SING N N 23 
LKM C12 S11  SING Y N 24 
LKM S11 O33  DOUB N N 25 
LKM S11 O32  DOUB Y N 26 
LKM S11 N    SING Y N 27 
LKM N   CA   SING Y N 28 
LKM CA  C    SING Y N 29 
LKM CA  CB   SING N N 30 
LKM C   O    SING Y N 31 
LKM C   OXT  DOUB N N 32 
LKM CB  CG   SING Y N 33 
LKM CG  CD   SING N N 34 
LKM CD  OE1  SING N N 35 
LKM CD  OE2  DOUB N N 36 
LKM C28 H28  SING N N 37 
LKM C26 H26  SING N N 38 
LKM C29 H29  SING N N 39 
LKM C23 H231 SING N N 40 
LKM C23 H232 SING N N 41 
LKM C19 H19  SING N N 42 
LKM C21 H21  SING N N 43 
LKM C18 H18  SING N N 44 
LKM C14 H14  SING N N 45 
LKM C17 H17  SING N N 46 
LKM C13 H13  SING N N 47 
LKM N   H    SING N N 48 
LKM CA  HA   SING N N 49 
LKM CB  HBC1 SING N N 50 
LKM CB  HBC2 SING N N 51 
LKM O   HB   SING N N 52 
LKM CG  HGC1 SING N N 53 
LKM CG  HGC2 SING N N 54 
LKM OE1 HE1  SING N N 55 
# 
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 
LKM SMILES           ACDLabs              10.04 O=C(O)C(NS(=O)(=O)c1ccc3c(c1)ccc(OCc2ccc(C#N)cc2F)c3)CCC(=O)O                                                                                                                                 
LKM InChI            InChI                1.02b InChI=1/C23H19FN2O7S/c24-20-9-14(12-25)1-2-17(20)13-33-18-5-3-16-11-19(6-4-15(16)10-18)34(31,32)26-21(23(29)30)7-8-22(27)28/h1-6,9-11,21,26H,7-8,13H2,(H,27,28)(H,29,30)/t21-/m1/s1/f/h27,29H 
LKM InChIKey         InChI                1.02b IRJUSGUHNFMVCK-KEVSMWGPDS                                                                                                                                                                     
LKM SMILES_CANONICAL CACTVS               3.341 OC(=O)CC[C@@H](N[S](=O)(=O)c1ccc2cc(OCc3ccc(cc3F)C#N)ccc2c1)C(O)=O                                                                                                                            
LKM SMILES           CACTVS               3.341 OC(=O)CC[CH](N[S](=O)(=O)c1ccc2cc(OCc3ccc(cc3F)C#N)ccc2c1)C(O)=O                                                                                                                              
LKM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1C#N)F)COc2ccc3cc(ccc3c2)S(=O)(=O)N[C@H](CCC(=O)O)C(=O)O                                                                                                                             
LKM SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1C#N)F)COc2ccc3cc(ccc3c2)S(=O)(=O)NC(CCC(=O)O)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 
LKM "SYSTEMATIC NAME" ACDLabs              10.04 "N-({6-[(4-cyano-2-fluorobenzyl)oxy]naphthalen-2-yl}sulfonyl)-D-glutamic acid"                 
LKM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-2-[[6-[(4-cyano-2-fluoro-phenyl)methoxy]naphthalen-2-yl]sulfonylamino]pentanedioic acid" 
# 
