data_AN2
# 
_chem_comp.id                                    AN2 
_chem_comp.name                                  "AMP PHOSPHORAMIDATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H16 N6 O9 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-17 
_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                        426.216 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AN2 
_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        ? 
_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 
AN2 N3B    N3B  N 0 1 N N N -24.288 37.133 38.298 -6.478 2.318  -1.130 N3B    AN2 1  
AN2 PB     PB   P 0 1 N N S -23.254 37.553 39.529 -5.565 1.274  -0.176 PB     AN2 2  
AN2 O2B    O2B  O 0 1 N N N -21.802 37.412 38.879 -4.927 2.093  1.055  O2B    AN2 3  
AN2 O1B    O1B  O 0 1 N N N -23.473 38.944 39.989 -6.434 0.196  0.346  O1B    AN2 4  
AN2 O3A    O3A  O 0 1 N N N -23.434 36.259 40.586 -4.384 0.631  -1.062 O3A    AN2 5  
AN2 PA     PA   P 0 1 N N S -22.856 35.851 42.104 -3.556 -0.350 -0.091 PA     AN2 6  
AN2 O1A    O1A  O 0 1 N N N -21.880 34.754 41.966 -3.415 0.278  1.242  O1A    AN2 7  
AN2 O2A    O2A  O 0 1 N N N -22.478 37.011 42.990 -4.341 -1.749 0.055  O2A    AN2 8  
AN2 "O5'"  O5*  O 0 1 N N N -24.263 35.151 42.436 -2.096 -0.617 -0.716 "O5'"  AN2 9  
AN2 "C5'"  C5*  C 0 1 N N N -25.507 35.927 42.231 -1.373 -1.393 0.241  "C5'"  AN2 10 
AN2 "C4'"  C4*  C 0 1 N N R -26.503 35.748 43.431 0.031  -1.683 -0.294 "C4'"  AN2 11 
AN2 "O4'"  O4*  O 0 1 N N N -26.881 34.332 43.272 0.794  -0.460 -0.391 "O4'"  AN2 12 
AN2 "C3'"  C3*  C 0 1 N N S -25.996 35.853 44.869 0.819  -2.561 0.704  "C3'"  AN2 13 
AN2 "O3'"  O3*  O 0 1 N N N -26.132 37.187 45.419 0.774  -3.933 0.307  "O3'"  AN2 14 
AN2 "C2'"  C2*  C 0 1 N N R -26.898 34.814 45.604 2.265  -2.019 0.621  "C2'"  AN2 15 
AN2 "O2'"  O2*  O 0 1 N N N -28.196 35.340 46.009 3.158  -3.041 0.174  "O2'"  AN2 16 
AN2 "C1'"  C1*  C 0 1 N N R -27.013 33.636 44.574 2.177  -0.876 -0.414 "C1'"  AN2 17 
AN2 N9     N9   N 0 1 Y N N -25.898 32.573 44.892 3.050  0.234  -0.023 N9     AN2 18 
AN2 C8     C8   C 0 1 Y N N -24.681 32.586 44.327 2.687  1.328  0.704  C8     AN2 19 
AN2 N7     N7   N 0 1 Y N N -23.947 31.581 44.853 3.711  2.114  0.867  N7     AN2 20 
AN2 C5     C5   C 0 1 Y N N -24.662 30.927 45.761 4.795  1.573  0.261  C5     AN2 21 
AN2 C4     C4   C 0 1 Y N N -25.911 31.541 45.789 4.383  0.363  -0.322 C4     AN2 22 
AN2 N3     N3   N 0 1 Y N N -26.829 31.058 46.665 5.270  -0.368 -0.989 N3     AN2 23 
AN2 C2     C2   C 0 1 Y N N -26.596 30.021 47.470 6.517  0.035  -1.108 C2     AN2 24 
AN2 N1     N1   N 0 1 Y N N -25.382 29.367 47.457 6.950  1.166  -0.582 N1     AN2 25 
AN2 C6     C6   C 0 1 Y N N -24.382 29.839 46.592 6.135  1.963  0.102  C6     AN2 26 
AN2 N6     N6   N 0 1 N N N -23.201 29.246 46.557 6.598  3.147  0.649  N6     AN2 27 
AN2 H3B1   1H3B H 0 0 N N N -24.267 37.839 37.590 -7.201 2.695  -0.537 H3B1   AN2 28 
AN2 H3B2   2H3B H 0 0 N N N -25.218 37.049 38.657 -5.874 3.088  -1.377 H3B2   AN2 29 
AN2 HO2B   BHO2 H 0 0 N N N -21.880 37.384 37.933 -4.369 2.784  0.672  HO2B   AN2 30 
AN2 HO2A   AHO2 H 0 0 N N N -22.399 36.711 43.888 -4.411 -2.124 -0.833 HO2A   AN2 31 
AN2 "H5'1" 1H5* H 0 0 N N N -25.997 35.559 41.317 -1.896 -2.333 0.418  "H5'1" AN2 32 
AN2 "H5'2" 2H5* H 0 0 N N N -25.249 36.992 42.141 -1.297 -0.838 1.177  "H5'2" AN2 33 
AN2 "H4'"  H4*  H 0 1 N N N -27.243 36.559 43.360 -0.028 -2.172 -1.266 "H4'"  AN2 34 
AN2 "H3'"  H3*  H 0 1 N N N -24.919 35.654 44.966 0.422  -2.443 1.712  "H3'"  AN2 35 
AN2 HA     HA   H 0 1 N N N -26.162 37.138 46.367 1.280  -4.431 0.964  HA     AN2 36 
AN2 "H2'"  H2*  H 0 1 N N N -26.462 34.502 46.565 2.584  -1.632 1.589  "H2'"  AN2 37 
AN2 HB     HB   H 0 1 N N N -28.212 35.454 46.952 3.123  -3.751 0.830  HB     AN2 38 
AN2 "H1'"  H1*  H 0 1 N N N -27.946 33.053 44.595 2.448  -1.240 -1.405 "H1'"  AN2 39 
AN2 H8     H8   H 0 1 N N N -24.344 33.285 43.576 1.695  1.515  1.088  H8     AN2 40 
AN2 H2     H2   H 0 1 N N N -27.371 29.687 48.144 7.213  -0.583 -1.656 H2     AN2 41 
AN2 H6N1   1H6N H 0 0 N N N -22.523 29.826 47.009 7.527  3.404  0.535  H6N1   AN2 42 
AN2 H6N2   2H6N H 0 0 N N N -22.931 29.096 45.606 5.993  3.723  1.142  H6N2   AN2 43 
# 
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 
AN2 N3B   PB     SING N N 1  
AN2 N3B   H3B1   SING N N 2  
AN2 N3B   H3B2   SING N N 3  
AN2 PB    O2B    SING N N 4  
AN2 PB    O1B    DOUB N N 5  
AN2 PB    O3A    SING N N 6  
AN2 O2B   HO2B   SING N N 7  
AN2 O3A   PA     SING N N 8  
AN2 PA    O1A    DOUB N N 9  
AN2 PA    O2A    SING N N 10 
AN2 PA    "O5'"  SING N N 11 
AN2 O2A   HO2A   SING N N 12 
AN2 "O5'" "C5'"  SING N N 13 
AN2 "C5'" "C4'"  SING N N 14 
AN2 "C5'" "H5'1" SING N N 15 
AN2 "C5'" "H5'2" SING N N 16 
AN2 "C4'" "O4'"  SING N N 17 
AN2 "C4'" "C3'"  SING N N 18 
AN2 "C4'" "H4'"  SING N N 19 
AN2 "O4'" "C1'"  SING N N 20 
AN2 "C3'" "O3'"  SING N N 21 
AN2 "C3'" "C2'"  SING N N 22 
AN2 "C3'" "H3'"  SING N N 23 
AN2 "O3'" HA     SING N N 24 
AN2 "C2'" "O2'"  SING N N 25 
AN2 "C2'" "C1'"  SING N N 26 
AN2 "C2'" "H2'"  SING N N 27 
AN2 "O2'" HB     SING N N 28 
AN2 "C1'" N9     SING N N 29 
AN2 "C1'" "H1'"  SING N N 30 
AN2 N9    C8     SING Y N 31 
AN2 N9    C4     SING Y N 32 
AN2 C8    N7     DOUB Y N 33 
AN2 C8    H8     SING N N 34 
AN2 N7    C5     SING Y N 35 
AN2 C5    C4     DOUB Y N 36 
AN2 C5    C6     SING Y N 37 
AN2 C4    N3     SING Y N 38 
AN2 N3    C2     DOUB Y N 39 
AN2 C2    N1     SING Y N 40 
AN2 C2    H2     SING N N 41 
AN2 N1    C6     DOUB Y N 42 
AN2 C6    N6     SING N N 43 
AN2 N6    H6N1   SING N N 44 
AN2 N6    H6N2   SING N N 45 
# 
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 
AN2 SMILES           ACDLabs              10.04 O=P(O)(OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)N                                                                                                                                                     
AN2 InChI            InChI                1.02b InChI=1/C10H16N6O9P2/c11-8-5-9(14-2-13-8)16(3-15-5)10-7(18)6(17)4(24-10)1-23-27(21,22)25-26(12,19)20/h2-4,6-7,10,17-18H,1H2,(H,21,22)(H2,11,13,14)(H3,12,19,20)/t4-,6-,7-,10-/m1/s1/f/h19,21H,11-12H2 
AN2 InChIKey         InChI                1.02b FQMDCEJHLOLKLI-JWPCQUJUDG                                                                                                                                                                             
AN2 SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@](N)(O)=O)[C@@H](O)[C@H]3O                                                                                                                            
AN2 SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](N)(O)=O)[CH](O)[CH]3O                                                                                                                                     
AN2 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)O[P@](=O)(N)O)O)O)N                                                                                                                       
AN2 SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(N)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 
AN2 "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(S)-amino(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine"                                        
AN2 "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]oxyphosphonamidic acid" 
# 
