data_A12
# 
_chem_comp.id                                    A12 
_chem_comp.name                                  "PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H17 N5 O9 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "ALPHA,BETA-METHYLENEADENOSINE-5'-DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-12-15 
_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                        425.228 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A12 
_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        1HPU 
_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 
A12 PB     PB   P 0 1 N N N -2.904 -0.420 -1.838 -6.106 1.026  -0.312 PB     A12 1  
A12 O1B    O1B  O 0 1 N N N -1.601 -0.830 -2.460 -6.748 -0.266 0.019  O1B    A12 2  
A12 O2B    O2B  O 0 1 N N N -2.880 -0.654 -0.363 -5.912 1.889  1.033  O2B    A12 3  
A12 O3B    O3B  O 0 1 N N N -3.172 1.022  -2.074 -7.039 1.840  -1.341 O3B    A12 4  
A12 PA     PA   P 0 1 N N S -5.850 -0.876 -1.948 -3.425 -0.203 0.087  PA     A12 5  
A12 O1A    O1A  O 0 1 N N N -5.873 -0.862 -0.461 -4.066 -1.495 0.418  O1A    A12 6  
A12 O2A    O2A  O 0 1 N N N -6.860 -1.819 -2.490 -3.230 0.659  1.433  O2A    A12 7  
A12 C3A    C3A  C 0 1 N N N -4.236 -1.356 -2.511 -4.481 0.719  -1.078 C3A    A12 8  
A12 "O5'"  O5*  O 0 1 N N N -6.160 0.599  -2.462 -1.989 -0.474 -0.589 "O5'"  A12 9  
A12 "C5'"  C5*  C 0 1 N N N -6.136 0.837  -3.854 -1.253 -1.297 0.319  "C5'"  A12 10 
A12 "C4'"  C4*  C 0 1 N N R -7.018 2.009  -4.197 0.129  -1.593 -0.267 "C4'"  A12 11 
A12 "O4'"  O4*  O 0 1 N N N -6.428 3.242  -3.692 0.912  -0.383 -0.344 "O4'"  A12 12 
A12 "C3'"  C3*  C 0 1 N N S -7.147 2.222  -5.693 0.927  -2.521 0.676  "C3'"  A12 13 
A12 "O3'"  O3*  O 0 1 N N N -8.203 1.386  -6.173 0.844  -3.877 0.233  "O3'"  A12 14 
A12 "C2'"  C2*  C 0 1 N N R -7.457 3.712  -5.783 2.381  -2.004 0.570  "C2'"  A12 15 
A12 "O2'"  O2*  O 0 1 N N N -8.798 3.978  -5.471 3.240  -3.026 0.061  "O2'"  A12 16 
A12 "C1'"  C1*  C 0 1 N N R -6.582 4.277  -4.653 2.286  -0.823 -0.421 "C1'"  A12 17 
A12 N9     N9   N 0 1 Y N N -5.252 4.698  -5.096 3.191  0.256  -0.018 N9     A12 18 
A12 C8     C8   C 0 1 Y N N -4.069 4.025  -4.919 2.870  1.330  0.758  C8     A12 19 
A12 N7     N7   N 0 1 Y N N -3.024 4.642  -5.428 3.913  2.091  0.918  N7     A12 20 
A12 C5     C5   C 0 1 Y N N -3.557 5.801  -5.970 4.969  1.552  0.262  C5     A12 21 
A12 C6     C6   C 0 1 Y N N -2.965 6.882  -6.634 6.312  1.923  0.077  C6     A12 22 
A12 N6     N6   N 0 1 N N N -1.655 6.979  -6.857 6.813  3.078  0.651  N6     A12 23 
A12 N1     N1   N 0 1 Y N N -3.771 7.877  -7.062 7.091  1.135  -0.658 N1     A12 24 
A12 C2     C2   C 0 1 Y N N -5.082 7.790  -6.807 6.621  0.031  -1.210 C2     A12 25 
A12 N3     N3   N 0 1 Y N N -5.760 6.828  -6.174 5.370  -0.352 -1.069 N3     A12 26 
A12 C4     C4   C 0 1 Y N N -4.928 5.849  -5.778 4.516  0.371  -0.351 C4     A12 27 
A12 HOB2   2HOB H 0 0 N N N -2.875 -1.588 -0.190 -5.492 2.720  0.774  HOB2   A12 28 
A12 HXT    HXT  H 0 1 N N N -3.229 1.474  -1.241 -7.887 1.982  -0.898 HXT    A12 29 
A12 HOA2   2HOA H 0 0 N N N -7.499 -2.020 -1.817 -2.810 1.491  1.173  HOA2   A12 30 
A12 H3A1   1H3A H 0 0 N N N -4.086 -2.393 -2.177 -4.008 1.670  -1.322 H3A1   A12 31 
A12 H3A2   2H3A H 0 0 N N N -4.213 -1.232 -3.604 -4.613 0.135  -1.989 H3A2   A12 32 
A12 "H5'1" 1H5* H 0 0 N N N -6.506 -0.057 -4.378 -1.789 -2.232 0.477  "H5'1" A12 33 
A12 "H5'2" 2H5* H 0 0 N N N -5.104 1.057  -4.166 -1.141 -0.777 1.270  "H5'2" A12 34 
A12 "H4'"  H4*  H 0 1 N N N -7.998 1.783  -3.751 0.032  -2.047 -1.253 "H4'"  A12 35 
A12 "H3'"  H3*  H 0 1 N N N -6.267 1.963  -6.300 0.562  -2.431 1.699  "H3'"  A12 36 
A12 "HO3'" *HO3 H 0 0 N N N -8.808 1.201  -5.464 1.358  -4.407 0.857  "HO3'" A12 37 
A12 "H2'"  H2*  H 0 1 N N N -7.276 4.126  -6.786 2.735  -1.657 1.541  "H2'"  A12 38 
A12 "HO2'" *HO2 H 0 0 N N N -8.898 4.038  -4.528 3.210  -3.757 0.693  "HO2'" A12 39 
A12 "H1'"  H1*  H 0 1 N N N -7.078 5.173  -4.252 2.521  -1.157 -1.432 "H1'"  A12 40 
A12 H8     H8   H 0 1 N N N -4.002 3.076  -4.409 1.893  1.522  1.177  H8     A12 41 
A12 HN61   1HN6 H 0 0 N N N -0.976 6.300  -6.577 7.743  3.321  0.519  HN61   A12 42 
A12 HN62   2HN6 H 0 0 N N N -1.447 7.827  -7.345 6.233  3.646  1.182  HN62   A12 43 
A12 H2     H2   H 0 1 N N N -5.678 8.617  -7.164 7.289  -0.579 -1.800 H2     A12 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 
A12 PB    O1B    DOUB N N 1  
A12 PB    O2B    SING N N 2  
A12 PB    O3B    SING N N 3  
A12 PB    C3A    SING N N 4  
A12 O2B   HOB2   SING N N 5  
A12 O3B   HXT    SING N N 6  
A12 PA    O1A    DOUB N N 7  
A12 PA    O2A    SING N N 8  
A12 PA    C3A    SING N N 9  
A12 PA    "O5'"  SING N N 10 
A12 O2A   HOA2   SING N N 11 
A12 C3A   H3A1   SING N N 12 
A12 C3A   H3A2   SING N N 13 
A12 "O5'" "C5'"  SING N N 14 
A12 "C5'" "C4'"  SING N N 15 
A12 "C5'" "H5'1" SING N N 16 
A12 "C5'" "H5'2" SING N N 17 
A12 "C4'" "O4'"  SING N N 18 
A12 "C4'" "C3'"  SING N N 19 
A12 "C4'" "H4'"  SING N N 20 
A12 "O4'" "C1'"  SING N N 21 
A12 "C3'" "O3'"  SING N N 22 
A12 "C3'" "C2'"  SING N N 23 
A12 "C3'" "H3'"  SING N N 24 
A12 "O3'" "HO3'" SING N N 25 
A12 "C2'" "O2'"  SING N N 26 
A12 "C2'" "C1'"  SING N N 27 
A12 "C2'" "H2'"  SING N N 28 
A12 "O2'" "HO2'" SING N N 29 
A12 "C1'" N9     SING N N 30 
A12 "C1'" "H1'"  SING N N 31 
A12 N9    C8     SING Y N 32 
A12 N9    C4     SING Y N 33 
A12 C8    N7     DOUB Y N 34 
A12 C8    H8     SING N N 35 
A12 N7    C5     SING Y N 36 
A12 C5    C6     SING Y N 37 
A12 C5    C4     DOUB Y N 38 
A12 C6    N6     SING N N 39 
A12 C6    N1     DOUB Y N 40 
A12 N6    HN61   SING N N 41 
A12 N6    HN62   SING N N 42 
A12 N1    C2     SING Y N 43 
A12 C2    N3     DOUB Y N 44 
A12 C2    H2     SING N N 45 
A12 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 
A12 SMILES           ACDLabs              10.04 O=P(O)(O)CP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O                                                                                                                                                         
A12 InChI            InChI                1.02b InChI=1/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1/f/h19-20,22H,12H2 
A12 InChIKey         InChI                1.02b OLCWZBFDIYXLAA-BHZLFSNMDP                                                                                                                                                                                 
A12 SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@](O)(=O)C[P](O)(O)=O)[C@@H](O)[C@H]3O                                                                                                                                  
A12 SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)C[P](O)(O)=O)[CH](O)[CH]3O                                                                                                                                         
A12 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)(CP(=O)(O)O)O)O)O)N                                                                                                                              
A12 SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(CP(=O)(O)O)O)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 
A12 "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-hydroxy(phosphonomethyl)phosphoryl]adenosine"                                                           
A12 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid" 
# 
