data_LYA
# 
_chem_comp.id                                    LYA 
_chem_comp.name                                  "2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H21 N5 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         LY231514 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-08-24 
_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                        427.411 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LYA 
_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        1JU6 
_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 
LYA C1   C1   C 0 1 Y N N 46.416 62.028 53.684 -0.958 0.986  0.861  C1   LYA 1  
LYA C2   C2   C 0 1 Y N N 45.835 63.024 52.857 -2.114 1.405  0.227  C2   LYA 2  
LYA C3   C3   C 0 1 Y N N 44.935 63.985 53.403 -2.270 1.208  -1.129 C3   LYA 3  
LYA C4   C4   C 0 1 Y N N 44.587 63.979 54.793 -1.258 0.584  -1.861 C4   LYA 4  
LYA C5   C5   C 0 1 Y N N 45.189 62.961 55.606 -0.095 0.164  -1.215 C5   LYA 5  
LYA C6   C6   C 0 1 Y N N 46.088 62.004 55.062 0.050  0.372  0.141  C6   LYA 6  
LYA C7   C7   C 0 1 N N N 47.396 60.989 53.087 -0.795 1.204  2.343  C7   LYA 7  
LYA C8   C8   C 0 1 N N N 46.744 59.643 52.619 -1.346 -0.004 3.101  C8   LYA 8  
LYA C9   C9   C 0 1 Y N N 46.395 58.717 53.786 -1.183 0.214  4.583  C9   LYA 9  
LYA C10  C10  C 0 1 Y N N 47.297 58.162 54.691 -2.067 0.796  5.413  C10  LYA 10 
LYA N11  N11  N 0 1 Y N N 46.633 57.373 55.635 -1.557 0.809  6.685  N11  LYA 11 
LYA C12  C12  C 0 1 Y N N 45.299 57.430 55.322 -0.328 0.233  6.702  C12  LYA 12 
LYA C13  C13  C 0 1 Y N N 45.158 58.257 54.177 -0.034 -0.165 5.401  C13  LYA 13 
LYA C14  C14  C 0 1 Y N N 43.726 58.494 53.600 1.247  -0.821 5.142  C14  LYA 14 
LYA O15  O15  O 0 1 N N N 43.480 59.177 52.628 1.545  -1.187 4.016  O15  LYA 15 
LYA N16  N16  N 0 1 Y N N 42.705 57.876 54.257 2.088  -1.013 6.172  N16  LYA 16 
LYA C17  C17  C 0 1 Y N N 42.921 57.040 55.435 1.775  -0.622 7.389  C17  LYA 17 
LYA N18  N18  N 0 1 Y N N 44.115 56.843 55.910 0.598  -0.014 7.686  N18  LYA 18 
LYA N19  N19  N 0 1 N N N 41.846 56.450 56.052 2.672  -0.845 8.399  N19  LYA 19 
LYA C20  C20  C 0 1 N N N 43.624 64.985 55.462 -1.418 0.370  -3.315 C20  LYA 20 
LYA O21  O21  O 0 1 N N N 43.380 64.913 56.674 -2.433 0.736  -3.876 O21  LYA 21 
LYA N22  N22  N 0 1 N N N 43.055 65.957 54.700 -0.439 -0.232 -4.019 N22  LYA 22 
LYA C23  C23  C 0 1 N N S 42.127 67.014 55.178 -0.598 -0.444 -5.460 C23  LYA 23 
LYA C24  C24  C 0 1 N N N 42.857 68.356 55.488 0.774  -0.416 -6.134 C24  LYA 24 
LYA C25  C25  C 0 1 N N N 44.000 68.215 56.542 1.435  0.941  -5.889 C25  LYA 25 
LYA C26  C26  C 0 1 N N N 44.833 69.429 56.950 2.788  0.969  -6.553 C26  LYA 26 
LYA O27  O27  O 0 1 N N N 45.658 69.299 57.875 3.183  0.001  -7.160 O27  LYA 27 
LYA O28  O28  O 0 1 N N N 44.695 70.512 56.345 3.554  2.068  -6.470 O28  LYA 28 
LYA C29  C29  C 0 1 N N N 40.945 67.108 54.157 -1.249 -1.782 -5.702 C29  LYA 29 
LYA O30  O30  O 0 1 N N N 39.843 67.614 54.469 -1.947 -1.947 -6.674 O30  LYA 30 
LYA O31  O31  O 0 1 N N N 41.129 66.643 53.008 -1.053 -2.790 -4.837 O31  LYA 31 
LYA HC2  HC2  H 0 1 N N N 46.084 63.051 51.782 -2.896 1.886  0.794  HC2  LYA 32 
LYA HC3  HC3  H 0 1 N N N 44.499 64.748 52.736 -3.173 1.535  -1.623 HC3  LYA 33 
LYA HC5  HC5  H 0 1 N N N 44.953 62.912 56.682 0.691  -0.318 -1.775 HC5  LYA 34 
LYA HC6  HC6  H 0 1 N N N 46.535 61.235 55.715 0.949  0.047  0.642  HC6  LYA 35 
LYA HC71 1HC7 H 0 0 N N N 47.974 61.445 52.250 -1.342 2.099  2.641  HC71 LYA 36 
LYA HC72 2HC7 H 0 0 N N N 48.221 60.783 53.807 0.261  1.330  2.578  HC72 LYA 37 
LYA HC81 1HC8 H 0 0 N N N 45.851 59.832 51.978 -0.799 -0.899 2.804  HC81 LYA 38 
LYA HC82 2HC8 H 0 0 N N N 47.391 59.122 51.875 -2.403 -0.129 2.867  HC82 LYA 39 
LYA H10  H10  H 0 1 N N N 48.387 58.325 54.663 -3.028 1.192  5.122  H10  LYA 40 
LYA H11  H11  H 0 1 N N N 47.045 56.852 56.408 -2.008 1.177  7.461  H11  LYA 41 
LYA H18  H18  H 0 1 N N N 44.099 57.106 56.895 0.411  0.250  8.600  H18  LYA 42 
LYA H191 1H19 H 0 0 N N N 41.996 55.866 56.874 3.517  -1.281 8.210  H191 LYA 43 
LYA H192 2H19 H 0 0 N N N 41.329 55.908 55.358 2.463  -0.562 9.303  H192 LYA 44 
LYA H22  H22  H 0 1 N N N 43.338 65.890 53.722 0.369  -0.524 -3.572 H22  LYA 45 
LYA H23  H23  H 0 1 N N N 41.695 66.745 56.170 -1.224 0.344  -5.877 H23  LYA 46 
LYA H241 1H24 H 0 0 N N N 43.240 68.822 54.550 1.400  -1.205 -5.717 H241 LYA 47 
LYA H242 2H24 H 0 0 N N N 42.127 69.139 55.799 0.656  -0.574 -7.206 H242 LYA 48 
LYA H251 1H25 H 0 0 N N N 43.570 67.760 57.464 0.809  1.730  -6.306 H251 LYA 49 
LYA H252 2H25 H 0 0 N N N 44.695 67.413 56.198 1.553  1.099  -4.817 H252 LYA 50 
LYA H28  H28  H 0 1 N N N 45.213 71.266 56.598 4.422  2.086  -6.896 H28  LYA 51 
LYA H31  H31  H 0 1 N N N 40.411 66.700 52.388 -1.471 -3.648 -4.992 H31  LYA 52 
# 
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 
LYA C1  C2   DOUB Y N 1  
LYA C1  C6   SING Y N 2  
LYA C1  C7   SING N N 3  
LYA C2  C3   SING Y N 4  
LYA C2  HC2  SING N N 5  
LYA C3  C4   DOUB Y N 6  
LYA C3  HC3  SING N N 7  
LYA C4  C5   SING Y N 8  
LYA C4  C20  SING N N 9  
LYA C5  C6   DOUB Y N 10 
LYA C5  HC5  SING N N 11 
LYA C6  HC6  SING N N 12 
LYA C7  C8   SING N N 13 
LYA C7  HC71 SING N N 14 
LYA C7  HC72 SING N N 15 
LYA C8  C9   SING N N 16 
LYA C8  HC81 SING N N 17 
LYA C8  HC82 SING N N 18 
LYA C9  C10  DOUB Y N 19 
LYA C9  C13  SING Y N 20 
LYA C10 N11  SING Y N 21 
LYA C10 H10  SING N N 22 
LYA N11 C12  SING Y N 23 
LYA N11 H11  SING N N 24 
LYA C12 C13  DOUB Y N 25 
LYA C12 N18  SING Y N 26 
LYA C13 C14  SING Y N 27 
LYA C14 O15  DOUB N N 28 
LYA C14 N16  SING Y N 29 
LYA N16 C17  DOUB Y N 30 
LYA C17 N18  SING Y N 31 
LYA C17 N19  SING N N 32 
LYA N18 H18  SING N N 33 
LYA N19 H191 SING N N 34 
LYA N19 H192 SING N N 35 
LYA C20 O21  DOUB N N 36 
LYA C20 N22  SING N N 37 
LYA N22 C23  SING N N 38 
LYA N22 H22  SING N N 39 
LYA C23 C24  SING N N 40 
LYA C23 C29  SING N N 41 
LYA C23 H23  SING N N 42 
LYA C24 C25  SING N N 43 
LYA C24 H241 SING N N 44 
LYA C24 H242 SING N N 45 
LYA C25 C26  SING N N 46 
LYA C25 H251 SING N N 47 
LYA C25 H252 SING N N 48 
LYA C26 O27  DOUB N N 49 
LYA C26 O28  SING N N 50 
LYA O28 H28  SING N N 51 
LYA C29 O30  DOUB N N 52 
LYA C29 O31  SING N N 53 
LYA O31 H31  SING N N 54 
# 
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 
LYA SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)CCc2cnc3NC(=NC(=O)c23)N)CCC(=O)O 
LYA InChI            InChI                1.02b 
InChI=1/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1/f/h22-24,26,30H,21H2 
LYA InChIKey         InChI                1.02b WBXPDJSOTKVWSJ-TYHHIXACDE 
LYA SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c[nH]c2N1 
LYA SMILES           CACTVS               3.341 NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)c[nH]c2N1 
LYA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
LYA SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=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 
LYA "SYSTEMATIC NAME" ACDLabs              10.04 "N-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl}carbonyl)-L-glutamic acid"        
LYA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[4,5-e]pyrimidin-5-yl)ethyl]phenyl]carbonylamino]pentanedioic acid" 
# 
