data_GAP
# 
_chem_comp.id                                    GAP 
_chem_comp.name                                  "GLYCYL-ADENOSINE-5'-PHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H17 N6 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        404.273 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GAP 
_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        1GGM 
_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 
GAP N      N    N 1  1 N N N 19.308 24.462 37.709 -7.880 2.447  -0.410 N      GAP 1  
GAP CA     CA   C 0  1 N N N 19.540 23.669 36.462 -6.619 2.159  -1.106 CA     GAP 2  
GAP C      C    C 0  1 N N N 21.002 23.447 36.020 -5.815 1.171  -0.300 C      GAP 3  
GAP O      O    O 0  1 N N N 21.822 23.274 36.966 -6.249 0.750  0.747  O      GAP 4  
GAP PA     PA   P 0  1 N N N 22.787 23.211 34.246 -3.760 -0.298 0.116  PA     GAP 5  
GAP O1A    O1A  O 0  1 N N N 22.669 22.674 32.859 -4.511 -1.646 0.175  O1A    GAP 6  
GAP O2A    O2A  O -1 1 N N N 23.557 22.455 35.261 -3.562 0.245  1.549  O2A    GAP 7  
GAP O3A    O3A  O 0  1 N N N 21.272 23.443 34.774 -4.618 0.758  -0.745 O3A    GAP 8  
GAP "C5'"  C5*  C 0  1 N N N 22.626 25.788 33.772 -1.569 -1.364 0.289  "C5'"  GAP 9  
GAP "O5'"  O5*  O 0  1 N N N 23.425 24.667 34.131 -2.323 -0.515 -0.579 "O5'"  GAP 10 
GAP "C4'"  C4*  C 0  1 N N R 23.497 26.885 33.240 -0.185 -1.611 -0.316 "C4'"  GAP 11 
GAP "O4'"  O4*  O 0  1 N N N 24.465 27.152 34.270 0.578  -0.385 -0.343 "O4'"  GAP 12 
GAP "C3'"  C3*  C 0  1 N N S 24.312 26.566 32.000 0.633  -2.566 0.581  "C3'"  GAP 13 
GAP "O3'"  O3*  O 0  1 N N N 23.605 26.980 30.837 0.570  -3.902 0.079  "O3'"  GAP 14 
GAP "C2'"  C2*  C 0  1 N N R 25.532 27.457 32.164 2.078  -2.020 0.492  "C2'"  GAP 15 
GAP "O2'"  O2*  O 0  1 N N N 25.304 28.771 31.699 2.951  -3.003 -0.066 "O2'"  GAP 16 
GAP "C1'"  C1*  C 0  1 N N R 25.696 27.467 33.683 1.958  -0.798 -0.446 "C1'"  GAP 17 
GAP N9     N9   N 0  1 Y N N 26.671 26.547 34.212 2.847  0.277  0.000  N9     GAP 18 
GAP C8     C8   C 0  1 Y N N 26.474 25.289 34.708 2.512  1.311  0.824  C8     GAP 19 
GAP N7     N7   N 0  1 Y N N 27.562 24.736 35.181 3.544  2.081  1.013  N7     GAP 20 
GAP C5     C5   C 0  1 Y N N 28.542 25.699 34.969 4.605  1.589  0.329  C5     GAP 21 
GAP C6     C6   C 0  1 Y N N 29.915 25.742 35.273 5.940  1.991  0.154  C6     GAP 22 
GAP N6     N6   N 0  1 N N N 30.580 24.754 35.855 6.425  3.128  0.777  N6     GAP 23 
GAP N1     N1   N 0  1 Y N N 30.593 26.852 34.952 6.728  1.250  -0.619 N1     GAP 24 
GAP C2     C2   C 0  1 Y N N 29.925 27.843 34.352 6.274  0.164  -1.217 C2     GAP 25 
GAP N3     N3   N 0  1 Y N N 28.643 27.923 34.007 5.030  -0.247 -1.087 N3     GAP 26 
GAP C4     C4   C 0  1 Y N N 28.001 26.799 34.358 4.168  0.429  -0.334 C4     GAP 27 
GAP H1     1H   H 0  1 N N N 18.341 24.608 38.001 -8.418 3.109  -0.949 H1     GAP 28 
GAP H2A    2H   H 0  1 N N N 19.832 24.043 38.477 -8.407 1.594  -0.301 H2A    GAP 29 
GAP H3     3H   H 0  1 N N N 19.776 25.364 37.626 -7.681 2.838  0.499  H3     GAP 30 
GAP HA1    1HA  H 0  1 N N N 19.028 22.682 36.552 -6.049 3.081  -1.223 HA1    GAP 31 
GAP HA2    2HA  H 0  1 N N N 18.966 24.126 35.622 -6.834 1.737  -2.088 HA2    GAP 32 
GAP "H5'1" 1H5* H 0  0 N N N 21.815 25.512 33.057 -2.088 -2.315 0.408  "H5'1" GAP 33 
GAP "H5'2" 2H5* H 0  0 N N N 21.986 26.133 34.617 -1.460 -0.885 1.262  "H5'2" GAP 34 
GAP "H4'"  H4*  H 0  1 N N N 22.807 27.715 32.961 -0.279 -2.022 -1.321 "H4'"  GAP 35 
GAP "H3'"  H3*  H 0  1 N N N 24.542 25.480 31.892 0.272  -2.527 1.609  "H3'"  GAP 36 
GAP "HO'3" 3HO* H 0  0 N N N 24.115 26.780 30.060 1.097  -4.450 0.676  "HO'3" GAP 37 
GAP "H2'"  H2*  H 0  1 N N N 26.416 27.095 31.589 2.431  -1.711 1.475  "H2'"  GAP 38 
GAP "HO'2" 2HO* H 0  0 N N N 26.066 29.328 31.801 2.937  -3.762 0.533  "HO'2" GAP 39 
GAP "H1'"  H1*  H 0  1 N N N 26.061 28.491 33.927 2.193  -1.082 -1.472 "H1'"  GAP 40 
GAP H8     H8   H 0  1 N N N 25.507 24.758 34.725 1.534  1.467  1.256  H8     GAP 41 
GAP H61    H61  H 0  1 N N N 31.575 24.785 36.075 7.349  3.392  0.652  H61    GAP 42 
GAP H62    H62  H 0  1 N N N 30.425 23.917 35.291 5.839  3.662  1.335  H62    GAP 43 
GAP H2     H2   H 0  1 N N N 30.525 28.734 34.102 6.948  -0.409 -1.836 H2     GAP 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 
GAP N     CA     SING N N 1  
GAP N     H1     SING N N 2  
GAP N     H2A    SING N N 3  
GAP N     H3     SING N N 4  
GAP CA    C      SING N N 5  
GAP CA    HA1    SING N N 6  
GAP CA    HA2    SING N N 7  
GAP C     O      DOUB N N 8  
GAP C     O3A    SING N N 9  
GAP PA    O1A    DOUB N N 10 
GAP PA    O2A    SING N N 11 
GAP PA    O3A    SING N N 12 
GAP PA    "O5'"  SING N N 13 
GAP "C5'" "O5'"  SING N N 14 
GAP "C5'" "C4'"  SING N N 15 
GAP "C5'" "H5'1" SING N N 16 
GAP "C5'" "H5'2" SING N N 17 
GAP "C4'" "O4'"  SING N N 18 
GAP "C4'" "C3'"  SING N N 19 
GAP "C4'" "H4'"  SING N N 20 
GAP "O4'" "C1'"  SING N N 21 
GAP "C3'" "O3'"  SING N N 22 
GAP "C3'" "C2'"  SING N N 23 
GAP "C3'" "H3'"  SING N N 24 
GAP "O3'" "HO'3" SING N N 25 
GAP "C2'" "O2'"  SING N N 26 
GAP "C2'" "C1'"  SING N N 27 
GAP "C2'" "H2'"  SING N N 28 
GAP "O2'" "HO'2" SING N N 29 
GAP "C1'" N9     SING N N 30 
GAP "C1'" "H1'"  SING N N 31 
GAP N9    C8     SING Y N 32 
GAP N9    C4     SING Y N 33 
GAP C8    N7     DOUB Y N 34 
GAP C8    H8     SING N N 35 
GAP N7    C5     SING Y N 36 
GAP C5    C6     SING Y N 37 
GAP C5    C4     DOUB Y N 38 
GAP C6    N6     SING N N 39 
GAP C6    N1     DOUB Y N 40 
GAP N6    H61    SING N N 41 
GAP N6    H62    SING N N 42 
GAP N1    C2     SING Y N 43 
GAP C2    N3     DOUB Y N 44 
GAP C2    H2     SING N N 45 
GAP N3    C4     SING Y N 46 
# 
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 
GAP SMILES           ACDLabs              10.04 [O-]P(=O)(OC(=O)C[NH3+])OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O                                                                                                                                
GAP InChI            InChI                1.02b InChI=1/C12H17N6O8P/c13-1-6(19)26-27(22,23)24-2-5-8(20)9(21)12(25-5)18-4-17-7-10(14)15-3-16-11(7)18/h3-5,8-9,12,20-21H,1-2,13H2,(H,22,23)(H2,14,15,16)/t5-,8-,9-,12-/m1/s1/f/h13H,14H2 
GAP InChIKey         InChI                1.02b HROXHMRQKGGIFT-VZSDHLGPDP                                                                                                                                                              
GAP SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P]([O-])(=O)OC(=O)C[NH3+])[C@@H](O)[C@H]3O                                                                                                            
GAP SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P]([O-])(=O)OC(=O)C[NH3+])[CH](O)[CH]3O                                                                                                                  
GAP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)([O-])OC(=O)C[NH3+])O)O)N                                                                                                    
GAP SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)([O-])OC(=O)C[NH3+])O)O)N                                                                                                                          
# 
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 
GAP "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-{[(ammonioacetyl)oxy]phosphinato}adenosine"                                                     
GAP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl 2-azaniumylethanoyl phosphate" 
# 
