data_XIH
# 
_chem_comp.id                                    XIH 
_chem_comp.name                                  2-({8-[(3R)-3-AMINOPIPERIDIN-1-YL]-1,3-DIMETHYL-2,6-DIOXO-1,2,3,6-TETRAHYDRO-7H-PURIN-7-YL}METHYL)BENZONITRILE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 N7 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-03-29 
_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                        393.442 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XIH 
_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        2GBI 
_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 
XIH C5   C5   C 0 1 Y N N 17.130 40.577 -80.062 1.180  0.626  0.332  C5   XIH 1  
XIH C6   C6   C 0 1 Y N N 17.211 40.161 -78.782 0.769  1.833  -0.223 C6   XIH 2  
XIH C8   C8   C 0 1 Y N N 15.177 39.509 -79.495 -1.020 0.679  0.203  C8   XIH 3  
XIH C10  C10  C 0 1 N N N 12.968 38.927 -78.302 -2.740 0.524  1.694  C10  XIH 4  
XIH C13  C13  C 0 1 N N R 12.919 36.866 -80.465 -4.591 0.984  -0.450 C13  XIH 5  
XIH C15  C15  C 0 1 N N N 13.273 38.312 -80.708 -3.096 1.305  -0.508 C15  XIH 6  
XIH C17  C17  C 0 1 N N N 15.359 40.448 -81.909 -0.054 -1.435 1.186  C17  XIH 7  
XIH C20  C20  C 0 1 Y N N 15.701 39.237 -85.479 -1.397 -3.476 -1.693 C20  XIH 8  
XIH C21  C21  C 0 1 Y N N 16.187 37.929 -85.366 -0.354 -4.353 -1.933 C21  XIH 9  
XIH C22  C22  C 0 1 Y N N 16.434 37.342 -84.107 0.792  -4.292 -1.168 C22  XIH 10 
XIH C24  C24  C 0 1 N N N 16.482 37.337 -81.740 2.086  -3.272 0.647  C24  XIH 11 
XIH C28  C28  C 0 1 Y N N 19.539 41.127 -78.557 3.036  2.488  -0.404 C28  XIH 12 
XIH C    C    C 0 1 N N N 20.548 42.276 -80.528 4.877  1.075  0.309  C    XIH 13 
XIH N    N    N 0 1 Y N N 19.408 41.538 -79.882 3.444  1.325  0.131  N    XIH 14 
XIH C3   C3   C 0 1 Y N N 18.296 41.318 -80.664 2.554  0.380  0.500  C3   XIH 15 
XIH O    O    O 0 1 N N N 18.206 41.698 -81.864 2.938  -0.674 0.977  O    XIH 16 
XIH N7   N7   N 0 1 Y N N 15.968 39.468 -78.416 -0.563 1.817  -0.279 N7   XIH 17 
XIH N9   N9   N 0 1 N N N 13.826 38.948 -79.521 -2.348 0.330  0.294  N9   XIH 18 
XIH C11  C11  C 0 1 N N N 12.451 37.481 -78.021 -4.216 0.161  1.874  C11  XIH 19 
XIH C12  C12  C 0 1 N N N 11.897 36.799 -79.295 -5.072 1.085  1.002  C12  XIH 20 
XIH N14  N14  N 0 1 N N N 12.435 36.235 -81.705 -5.332 1.944  -1.279 N14  XIH 21 
XIH N16  N16  N 0 1 Y N N 15.797 40.157 -80.553 0.024  -0.096 0.597  N16  XIH 22 
XIH C18  C18  C 0 1 Y N N 15.696 39.435 -83.006 -0.159 -2.462 0.088  C18  XIH 23 
XIH C19  C19  C 0 1 Y N N 15.465 39.970 -84.308 -1.299 -2.533 -0.685 C19  XIH 24 
XIH C23  C23  C 0 1 Y N N 16.195 38.069 -82.935 0.900  -3.340 -0.152 C23  XIH 25 
XIH N25  N25  N 0 1 N N N 16.616 36.742 -80.775 3.027  -3.217 1.281  N25  XIH 26 
XIH N26  N26  N 0 1 Y N N 18.443 40.437 -78.003 1.731  2.762  -0.588 N26  XIH 27 
XIH C27  C27  C 0 1 N N N 18.494 39.964 -76.604 1.326  4.042  -1.174 C27  XIH 28 
XIH O29  O29  O 0 1 N N N 20.569 41.333 -77.868 3.867  3.314  -0.731 O29  XIH 29 
XIH H101 1H10 H 0 0 N N N 13.558 39.272 -77.440 -2.130 -0.114 2.333  H101 XIH 30 
XIH H102 2H10 H 0 0 N N N 12.104 39.589 -78.463 -2.587 1.567  1.972  H102 XIH 31 
XIH H13  H13  H 0 1 N N N 13.808 36.290 -80.169 -4.762 -0.026 -0.821 H13  XIH 32 
XIH H151 1H15 H 0 0 N N N 14.022 38.359 -81.512 -2.924 2.306  -0.113 H151 XIH 33 
XIH H152 2H15 H 0 0 N N N 12.351 38.846 -80.982 -2.756 1.260  -1.542 H152 XIH 34 
XIH H171 1H17 H 0 0 N N N 15.834 41.397 -82.198 0.842  -1.625 1.777  H171 XIH 35 
XIH H172 2H17 H 0 0 N N N 14.260 40.447 -81.855 -0.933 -1.499 1.828  H172 XIH 36 
XIH H20  H20  H 0 1 N N N 15.512 39.672 -86.449 -2.292 -3.527 -2.296 H20  XIH 37 
XIH H21  H21  H 0 1 N N N 16.377 37.357 -86.262 -0.437 -5.086 -2.722 H21  XIH 38 
XIH H22  H22  H 0 1 N N N 16.808 36.331 -84.048 1.605  -4.978 -1.356 H22  XIH 39 
XIH H1   1H   H 0 1 N N N 20.315 42.456 -81.588 5.442  1.937  -0.046 H1   XIH 40 
XIH H2   2H   H 0 1 N N N 20.698 43.238 -80.017 5.088  0.912  1.366  H2   XIH 41 
XIH H3   3H   H 0 1 N N N 21.465 41.673 -80.452 5.165  0.192  -0.261 H3   XIH 42 
XIH H111 1H11 H 0 0 N N N 11.645 37.536 -77.275 -4.375 -0.875 1.573  H111 XIH 43 
XIH H112 2H11 H 0 0 N N N 13.300 36.882 -77.658 -4.496 0.284  2.920  H112 XIH 44 
XIH H121 1H12 H 0 0 N N N 10.974 37.313 -79.600 -6.116 0.779  1.062  H121 XIH 45 
XIH H122 2H12 H 0 0 N N N 11.701 35.741 -79.065 -4.970 2.113  1.349  H122 XIH 46 
XIH H141 1H14 H 0 0 N N N 12.325 36.932 -82.413 -6.308 1.697  -1.207 H141 XIH 47 
XIH H142 2H14 H 0 0 N N N 13.097 35.550 -82.011 -5.228 2.847  -0.842 H142 XIH 48 
XIH H19  H19  H 0 1 N N N 15.093 40.980 -84.395 -2.117 -1.852 -0.504 H19  XIH 49 
XIH H271 1H27 H 0 0 N N N 18.507 38.864 -76.588 2.213  4.636  -1.395 H271 XIH 50 
XIH H272 2H27 H 0 0 N N N 19.404 40.348 -76.120 0.772  3.861  -2.095 H272 XIH 51 
XIH H273 3H27 H 0 0 N N N 17.609 40.328 -76.062 0.694  4.581  -0.469 H273 XIH 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 
XIH C5  C6   DOUB Y N 1  
XIH C5  C3   SING Y N 2  
XIH C5  N16  SING Y N 3  
XIH C6  N7   SING Y N 4  
XIH C6  N26  SING Y N 5  
XIH C8  N7   DOUB Y N 6  
XIH C8  N9   SING N N 7  
XIH C8  N16  SING Y N 8  
XIH C10 N9   SING N N 9  
XIH C10 C11  SING N N 10 
XIH C10 H101 SING N N 11 
XIH C10 H102 SING N N 12 
XIH C13 C15  SING N N 13 
XIH C13 C12  SING N N 14 
XIH C13 N14  SING N N 15 
XIH C13 H13  SING N N 16 
XIH C15 N9   SING N N 17 
XIH C15 H151 SING N N 18 
XIH C15 H152 SING N N 19 
XIH C17 N16  SING N N 20 
XIH C17 C18  SING N N 21 
XIH C17 H171 SING N N 22 
XIH C17 H172 SING N N 23 
XIH C20 C21  DOUB Y N 24 
XIH C20 C19  SING Y N 25 
XIH C20 H20  SING N N 26 
XIH C21 C22  SING Y N 27 
XIH C21 H21  SING N N 28 
XIH C22 C23  DOUB Y N 29 
XIH C22 H22  SING N N 30 
XIH C24 C23  SING N N 31 
XIH C24 N25  TRIP N N 32 
XIH C28 N    SING Y N 33 
XIH C28 N26  SING Y N 34 
XIH C28 O29  DOUB N N 35 
XIH C   N    SING N N 36 
XIH C   H1   SING N N 37 
XIH C   H2   SING N N 38 
XIH C   H3   SING N N 39 
XIH N   C3   SING Y N 40 
XIH C3  O    DOUB N N 41 
XIH C11 C12  SING N N 42 
XIH C11 H111 SING N N 43 
XIH C11 H112 SING N N 44 
XIH C12 H121 SING N N 45 
XIH C12 H122 SING N N 46 
XIH N14 H141 SING N N 47 
XIH N14 H142 SING N N 48 
XIH C18 C19  DOUB Y N 49 
XIH C18 C23  SING Y N 50 
XIH C19 H19  SING N N 51 
XIH N26 C27  SING N N 52 
XIH C27 H271 SING N N 53 
XIH C27 H272 SING N N 54 
XIH C27 H273 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 
XIH SMILES           ACDLabs              10.04 N#Cc1ccccc1Cn2c4c(nc2N3CCCC(N)C3)N(C(=O)N(C4=O)C)C                                                                                                           
XIH InChI            InChI                1.02b InChI=1/C20H23N7O2/c1-24-17-16(18(28)25(2)20(24)29)27(11-14-7-4-3-6-13(14)10-21)19(23-17)26-9-5-8-15(22)12-26/h3-4,6-7,15H,5,8-9,11-12,22H2,1-2H3/t15-/m1/s1 
XIH InChIKey         InChI                1.02b XJNKUWDMCBZMTG-OAHLLOKOBO                                                                                                                                    
XIH SMILES_CANONICAL CACTVS               3.341 CN1C(=O)N(C)c2nc(N3CCC[C@@H](N)C3)n(Cc4ccccc4C#N)c2C1=O                                                                                                      
XIH SMILES           CACTVS               3.341 CN1C(=O)N(C)c2nc(N3CCC[CH](N)C3)n(Cc4ccccc4C#N)c2C1=O                                                                                                        
XIH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN1c2c(n(c(n2)N3CCC[C@H](C3)N)Cc4ccccc4C#N)C(=O)N(C1=O)C                                                                                                     
XIH SMILES           "OpenEye OEToolkits" 1.5.0 CN1c2c(n(c(n2)N3CCCC(C3)N)Cc4ccccc4C#N)C(=O)N(C1=O)C                                                                                                         
# 
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 
XIH "SYSTEMATIC NAME" ACDLabs              10.04 2-({8-[(3R)-3-aminopiperidin-1-yl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl}methyl)benzonitrile 
XIH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[[8-[(3R)-3-aminopiperidin-1-yl]-1,3-dimethyl-2,6-dioxo-purin-7-yl]methyl]benzonitrile                       
# 
