data_AMA
# 
_chem_comp.id                                    AMA 
_chem_comp.name                                  "2-[(3-HYDROXY-2-METHYL-5-PHOSPHONOOXYMETHYL-PYRIDIN-4-YLMETHYL)-AMINO]-2-METHYL-SUCCINIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H19 N2 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N-PYRIDOXYL-2-METHYLASPARTIC ACID-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                   OBS 
_chem_comp.pdbx_replaced_by                      PLA 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        378.272 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AMA 
_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        1AMA 
_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 
AMA N1   N1   N 0 1 Y N N 43.522 15.830 45.036 3.176  0.555  2.733  N1   AMA 1  
AMA C2   C2   C 0 1 Y N N 44.740 15.531 45.473 3.766  0.357  1.572  C2   AMA 2  
AMA C2A  C2A  C 0 1 N N N 45.224 16.110 46.755 5.255  0.558  1.448  C2A  AMA 3  
AMA C3   C3   C 0 1 Y N N 45.511 14.662 44.673 3.031  -0.029 0.461  C3   AMA 4  
AMA O3   O3   O 0 1 N N N 46.712 14.338 45.085 3.645  -0.232 -0.734 O3   AMA 5  
AMA C4   C4   C 0 1 Y N N 44.958 14.165 43.485 1.659  -0.216 0.590  C4   AMA 6  
AMA C4A  C4A  C 0 1 N N N 45.790 13.306 42.682 0.823  -0.642 -0.588 C4A  AMA 7  
AMA C5   C5   C 0 1 Y N N 43.700 14.518 43.077 1.079  0.002  1.829  C5   AMA 8  
AMA C6   C6   C 0 1 Y N N 42.959 15.381 43.889 1.877  0.392  2.889  C6   AMA 9  
AMA C5A  C5A  C 0 1 N N N 43.014 14.073 41.827 -0.404 -0.180 2.019  C5A  AMA 10 
AMA OP4  OP4  O 0 1 N N N 43.165 12.683 41.501 -0.750 0.105  3.376  OP4  AMA 11 
AMA P    P    P 0 1 N N N 42.158 12.012 40.510 -2.340 -0.109 3.507  P    AMA 12 
AMA OP1  OP1  O 0 1 N N N 42.999 11.000 39.800 -2.678 -1.508 3.162  OP1  AMA 13 
AMA OP2  OP2  O 0 1 N N N 41.578 13.100 39.525 -2.800 0.197  5.018  OP2  AMA 14 
AMA OP3  OP3  O 0 1 N N N 40.983 11.534 41.280 -3.101 0.890  2.500  OP3  AMA 15 
AMA N    N    N 0 1 N N N 47.147 13.143 43.006 0.344  0.547  -1.304 N    AMA 16 
AMA CA   CA   C 0 1 N N S 48.027 12.300 42.178 -0.458 0.064  -2.435 CA   AMA 17 
AMA C    C    C 0 1 N N N 49.468 12.799 42.334 0.399  -0.790 -3.332 C    AMA 18 
AMA O    O    O 0 1 N N N 50.423 12.272 41.756 -0.099 -1.691 -3.965 O    AMA 19 
AMA CB2  CB2  C 0 1 N N N 47.962 10.803 42.385 -1.632 -0.763 -1.910 CB2  AMA 20 
AMA CB1  CB1  C 0 1 N N N 47.584 12.276 40.733 -0.992 1.259  -3.229 CB1  AMA 21 
AMA CG   CG   C 0 1 N N N 47.649 13.576 39.953 -1.816 0.764  -4.389 CG   AMA 22 
AMA OD1  OD1  O 0 1 N N N 48.579 14.404 40.042 -1.961 -0.422 -4.564 OD1  AMA 23 
AMA OD2  OD2  O 0 1 N N N 46.662 13.789 39.207 -2.388 1.641  -5.229 OD2  AMA 24 
AMA OXT  OXT  O 0 1 N N N 49.705 13.778 43.058 1.716  -0.552 -3.427 OXT  AMA 25 
AMA H2A1 1H2A H 0 0 N N N 46.246 15.859 47.121 5.767  -0.378 1.665  H2A1 AMA 26 
AMA H2A2 2H2A H 0 0 N N N 45.128 17.219 46.701 5.495  0.878  0.434  H2A2 AMA 27 
AMA H2A3 3H2A H 0 0 N N N 44.488 15.862 47.556 5.578  1.322  2.155  H2A3 AMA 28 
AMA HO3  HO3  H 0 1 N N N 47.231 13.752 44.546 3.629  0.612  -1.204 HO3  AMA 29 
AMA H4A1 1H4A H 0 0 N N N 45.314 12.298 42.634 1.427  -1.252 -1.260 H4A1 AMA 30 
AMA H4A2 2H4A H 0 0 N N N 45.717 13.636 41.619 -0.029 -1.223 -0.238 H4A2 AMA 31 
AMA H6   H6   H 0 1 N N N 41.937 15.705 43.626 1.430  0.564  3.857  H6   AMA 32 
AMA H5A1 1H5A H 0 0 N N N 41.932 14.339 41.869 -0.942 0.497  1.357  H5A1 AMA 33 
AMA H5A2 2H5A H 0 0 N N N 43.339 14.704 40.967 -0.676 -1.210 1.784  H5A2 AMA 34 
AMA HOP2 2HOP H 0 0 N N N 40.966 12.692 38.923 -3.757 0.057  5.053  HOP2 AMA 35 
AMA HOP3 3HOP H 0 0 N N N 40.371 11.126 40.678 -2.854 1.788  2.759  HOP3 AMA 36 
AMA HN   HN   H 0 1 N N N 47.205 12.812 43.969 -0.289 1.024  -0.681 HN   AMA 37 
AMA HB21 1HB2 H 0 0 N N N 48.628 10.165 41.758 -2.253 -0.145 -1.262 HB21 AMA 38 
AMA HB22 2HB2 H 0 0 N N N 48.138 10.572 43.461 -2.228 -1.121 -2.750 HB22 AMA 39 
AMA HB23 3HB2 H 0 0 N N N 46.907 10.460 42.267 -1.253 -1.614 -1.345 HB23 AMA 40 
AMA HB11 1HB1 H 0 0 N N N 48.156 11.490 40.186 -1.612 1.878  -2.580 HB11 AMA 41 
AMA HB12 2HB1 H 0 0 N N N 46.550 11.862 40.672 -0.155 1.850  -3.603 HB12 AMA 42 
AMA HD2  HD2  H 0 1 N N N 46.702 14.602 38.718 -2.916 1.324  -5.974 HD2  AMA 43 
AMA HXT  HXT  H 0 1 N N N 50.598 14.087 43.154 2.266  -1.101 -4.002 HXT  AMA 44 
# 
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 
AMA N1  C2   DOUB Y N 1  
AMA N1  C6   SING Y N 2  
AMA C2  C2A  SING N N 3  
AMA C2  C3   SING Y N 4  
AMA C2A H2A1 SING N N 5  
AMA C2A H2A2 SING N N 6  
AMA C2A H2A3 SING N N 7  
AMA C3  O3   SING N N 8  
AMA C3  C4   DOUB Y N 9  
AMA O3  HO3  SING N N 10 
AMA C4  C4A  SING N N 11 
AMA C4  C5   SING Y N 12 
AMA C4A N    SING N N 13 
AMA C4A H4A1 SING N N 14 
AMA C4A H4A2 SING N N 15 
AMA C5  C6   DOUB Y N 16 
AMA C5  C5A  SING N N 17 
AMA C6  H6   SING N N 18 
AMA C5A OP4  SING N N 19 
AMA C5A H5A1 SING N N 20 
AMA C5A H5A2 SING N N 21 
AMA OP4 P    SING N N 22 
AMA P   OP1  DOUB N N 23 
AMA P   OP2  SING N N 24 
AMA P   OP3  SING N N 25 
AMA OP2 HOP2 SING N N 26 
AMA OP3 HOP3 SING N N 27 
AMA N   CA   SING N N 28 
AMA N   HN   SING N N 29 
AMA CA  C    SING N N 30 
AMA CA  CB2  SING N N 31 
AMA CA  CB1  SING N N 32 
AMA C   O    DOUB N N 33 
AMA C   OXT  SING N N 34 
AMA CB2 HB21 SING N N 35 
AMA CB2 HB22 SING N N 36 
AMA CB2 HB23 SING N N 37 
AMA CB1 CG   SING N N 38 
AMA CB1 HB11 SING N N 39 
AMA CB1 HB12 SING N N 40 
AMA CG  OD1  DOUB N N 41 
AMA CG  OD2  SING N N 42 
AMA OD2 HD2  SING N N 43 
AMA OXT HXT  SING N N 44 
# 
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 
AMA SMILES           ACDLabs              10.04 O=C(O)C(NCc1c(cnc(c1O)C)COP(=O)(O)O)(C)CC(=O)O                                                                                                                              
AMA InChI            InChI                1.02b InChI=1/C13H19N2O9P/c1-7-11(18)9(8(4-14-7)6-24-25(21,22)23)5-15-13(2,12(19)20)3-10(16)17/h4,15,18H,3,5-6H2,1-2H3,(H,16,17)(H,19,20)(H2,21,22,23)/t13-/m0/s1/f/h16,19,21-22H 
AMA InChIKey         InChI                1.02b ZFKRUCNEKPIDBK-LDTOWYNPDC                                                                                                                                                   
AMA SMILES_CANONICAL CACTVS               3.341 Cc1ncc(CO[P](O)(O)=O)c(CN[C@@](C)(CC(O)=O)C(O)=O)c1O                                                                                                                        
AMA SMILES           CACTVS               3.341 Cc1ncc(CO[P](O)(O)=O)c(CN[C](C)(CC(O)=O)C(O)=O)c1O                                                                                                                          
AMA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c(c(cn1)COP(=O)(O)O)CN[C@@](C)(CC(=O)O)C(=O)O)O                                                                                                                        
AMA SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c(c(cn1)COP(=O)(O)O)CNC(C)(CC(=O)O)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 
AMA "SYSTEMATIC NAME" ACDLabs              10.04 "N-({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)-2-methyl-L-aspartic acid"          
AMA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylamino]-2-methyl-butanedioic acid" 
# 
