data_PLS
# 
_chem_comp.id                                    PLS 
_chem_comp.name                                  [3-HYDROXY-2-METHYL-5-PHOSPHONOOXYMETHYL-PYRIDIN-4-YLMETHYL]-SERINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H17 N2 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         PYRIDOXYL-SERINE-5-MONOPHOSPHATE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        336.235 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PLS 
_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        1BEU 
_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 
PLS N    N    N 0 1 N N N 80.033 17.390 10.482 -0.529 0.426  -1.727 N    PLS 1  
PLS CA   CA   C 0 1 N N S 78.707 18.098 10.417 -1.697 -0.057 -2.474 CA   PLS 2  
PLS CB   CB   C 0 1 N N N 78.738 19.501 10.925 -2.816 0.982  -2.401 CB   PLS 3  
PLS OG   OG   O 0 1 N N N 77.884 19.843 12.018 -3.953 0.511  -3.128 OG   PLS 4  
PLS C    C    C 0 1 N N N 78.055 18.088 8.941  -1.314 -0.282 -3.914 C    PLS 5  
PLS O    O    O 0 1 N N N 78.680 17.665 7.985  -1.874 -1.135 -4.562 O    PLS 6  
PLS OXT  OXT  O 0 1 N N N 76.940 18.625 8.702  -0.351 0.463  -4.477 OXT  PLS 7  
PLS N1   N1   N 0 1 Y N N 83.934 13.811 11.745 3.585  0.440  0.992  N1   PLS 8  
PLS C2   C2   C 0 1 Y N N 83.898 14.497 10.523 3.706  0.211  -0.300 C2   PLS 9  
PLS C2A  C2A  C 0 1 N N N 85.041 14.378 9.569  5.048  0.380  -0.965 C2A  PLS 10 
PLS C3   C3   C 0 1 Y N N 82.734 15.385 10.256 2.610  -0.177 -1.056 C3   PLS 11 
PLS O3   O3   O 0 1 N N N 82.605 16.219 9.196  2.740  -0.412 -2.388 O3   PLS 12 
PLS C4   C4   C 0 1 Y N N 81.708 15.533 11.377 1.378  -0.334 -0.428 C4   PLS 13 
PLS C4A  C4A  C 0 1 N N N 80.451 16.403 11.284 0.163  -0.762 -1.210 C4A  PLS 14 
PLS C5   C5   C 0 1 Y N N 81.845 14.766 12.581 1.296  -0.083 0.931  C5   PLS 15 
PLS C6   C6   C 0 1 Y N N 83.007 13.924 12.769 2.432  0.306  1.615  C6   PLS 16 
PLS C5A  C5A  C 0 1 N N N 80.840 14.930 13.718 -0.016 -0.233 1.655  C5A  PLS 17 
PLS O4P  O4P  O 0 1 N N N 79.644 14.132 13.614 0.163  0.080  3.037  O4P  PLS 18 
PLS P    P    P 0 1 N N N 79.486 12.769 13.919 -1.271 -0.099 3.746  P    PLS 19 
PLS O1P  O1P  O 0 1 N N N 79.612 12.725 15.416 -1.731 -1.496 3.581  O1P  PLS 20 
PLS O2P  O2P  O 0 1 N N N 78.111 12.538 13.581 -1.141 0.240  5.314  O2P  PLS 21 
PLS O3P  O3P  O 0 1 N N N 80.224 11.664 13.491 -2.335 0.899  3.066  O3P  PLS 22 
PLS HN   HN   H 0 1 N N N 80.722 18.132 10.598 -0.884 0.926  -0.926 HN   PLS 23 
PLS HA   HA   H 0 1 N N N 78.063 17.499 11.103 -2.043 -0.995 -2.040 HA   PLS 24 
PLS HB1  1HB  H 0 1 N N N 79.788 19.770 11.185 -3.093 1.145  -1.359 HB1  PLS 25 
PLS HB2  2HB  H 0 1 N N N 78.542 20.199 10.078 -2.470 1.920  -2.835 HB2  PLS 26 
PLS HOG  HOG  H 0 1 N N N 77.903 20.736 12.341 -4.633 1.195  -3.056 HOG  PLS 27 
PLS HXT  HXT  H 0 1 N N N 76.556 18.619 7.833  -0.105 0.319  -5.401 HXT  PLS 28 
PLS H2A1 1H2A H 0 0 N N N 85.012 14.923 8.597  5.592  -0.563 -0.930 H2A1 PLS 29 
PLS H2A2 2H2A H 0 0 N N N 85.978 14.658 10.103 4.904  0.678  -2.003 H2A2 PLS 30 
PLS H2A3 3H2A H 0 0 N N N 85.217 13.296 9.362  5.619  1.147  -0.442 H2A3 PLS 31 
PLS HO3  HO3  H 0 1 N N N 81.862 16.785 9.025  2.564  0.425  -2.838 HO3  PLS 32 
PLS H4A1 1H4A H 0 0 N N N 80.370 16.848 12.303 0.470  -1.394 -2.043 H4A1 PLS 33 
PLS H4A2 2H4A H 0 0 N N N 79.625 15.656 11.224 -0.509 -1.320 -0.559 H4A2 PLS 34 
PLS H6   H6   H 0 1 N N N 83.187 13.363 13.701 2.373  0.503  2.676  H6   PLS 35 
PLS H5A1 1H5A H 0 0 N N N 81.339 14.741 14.697 -0.751 0.444  1.221  H5A1 PLS 36 
PLS H5A2 2H5A H 0 0 N N N 80.570 16.005 13.835 -0.369 -1.260 1.559  H5A2 PLS 37 
PLS HOP2 2HOP H 0 0 N N N 78.004 11.616 13.787 -2.020 0.120  5.700  HOP2 PLS 38 
PLS HOP3 3HOP H 0 0 N N N 80.117 10.742 13.697 -1.998 1.796  3.196  HOP3 PLS 39 
# 
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 
PLS N   CA   SING N N 1  
PLS N   C4A  SING N N 2  
PLS N   HN   SING N N 3  
PLS CA  CB   SING N N 4  
PLS CA  C    SING N N 5  
PLS CA  HA   SING N N 6  
PLS CB  OG   SING N N 7  
PLS CB  HB1  SING N N 8  
PLS CB  HB2  SING N N 9  
PLS OG  HOG  SING N N 10 
PLS C   O    DOUB N N 11 
PLS C   OXT  SING N N 12 
PLS OXT HXT  SING N N 13 
PLS N1  C2   DOUB Y N 14 
PLS N1  C6   SING Y N 15 
PLS C2  C2A  SING N N 16 
PLS C2  C3   SING Y N 17 
PLS C2A H2A1 SING N N 18 
PLS C2A H2A2 SING N N 19 
PLS C2A H2A3 SING N N 20 
PLS C3  O3   SING N N 21 
PLS C3  C4   DOUB Y N 22 
PLS O3  HO3  SING N N 23 
PLS C4  C4A  SING N N 24 
PLS C4  C5   SING Y N 25 
PLS C4A H4A1 SING N N 26 
PLS C4A H4A2 SING N N 27 
PLS C5  C6   DOUB Y N 28 
PLS C5  C5A  SING N N 29 
PLS C6  H6   SING N N 30 
PLS C5A O4P  SING N N 31 
PLS C5A H5A1 SING N N 32 
PLS C5A H5A2 SING N N 33 
PLS O4P P    SING N N 34 
PLS P   O1P  DOUB N N 35 
PLS P   O2P  SING N N 36 
PLS P   O3P  SING N N 37 
PLS O2P HOP2 SING N N 38 
PLS O3P HOP3 SING N N 39 
# 
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 
PLS SMILES           ACDLabs              10.04 O=C(O)C(NCc1c(cnc(c1O)C)COP(=O)(O)O)CO                                                                                                              
PLS InChI            InChI                1.02b InChI=1/C11H17N2O8P/c1-6-10(15)8(3-13-9(4-14)11(16)17)7(2-12-6)5-21-22(18,19)20/h2,9,13-15H,3-5H2,1H3,(H,16,17)(H2,18,19,20)/t9-/m0/s1/f/h16,18-19H 
PLS InChIKey         InChI                1.02b ODVKKQWXKRZJLG-ZUTBFZTIDL                                                                                                                           
PLS SMILES_CANONICAL CACTVS               3.341 Cc1ncc(CO[P](O)(O)=O)c(CN[C@@H](CO)C(O)=O)c1O                                                                                                       
PLS SMILES           CACTVS               3.341 Cc1ncc(CO[P](O)(O)=O)c(CN[CH](CO)C(O)=O)c1O                                                                                                         
PLS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c(c(cn1)COP(=O)(O)O)CN[C@@H](CO)C(=O)O)O                                                                                                       
PLS SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c(c(cn1)COP(=O)(O)O)CNC(CO)C(=O)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 
PLS "SYSTEMATIC NAME" ACDLabs              10.04 N-({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)-L-serine                          
PLS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-3-hydroxy-2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylamino]propanoic acid" 
# 
