data_5AA
# 
_chem_comp.id                                    5AA 
_chem_comp.name                                  "N6-DIMETHYL-3'-AMINO-ADENOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C12 H19 N6 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         
;PUROMYCIN AMINONUCLEOSIDE-5'-MONOPHOSPHATE
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-29 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        374.290 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     5AA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1VQ7 
_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 
5AA P      P    P 0 1 N N N 73.542 116.104 106.620 6.420  -2.698 -1.384 P      5AA 1  
5AA OP3    O3P  O 0 1 N Y N 72.424 115.131 106.499 5.930  -2.624 -2.923 OP3    5AA 2  
5AA OP2    O2P  O 0 1 N N N 74.943 115.622 106.526 6.083  -4.222 -0.959 OP2    5AA 3  
5AA "O5'"  O5*  O 0 1 N N N 73.323 117.245 105.531 5.302  -1.845 -0.583 "O5'"  5AA 4  
5AA "C5'"  C5*  C 0 1 N N N 72.069 117.946 105.466 3.936  -2.187 -0.760 "C5'"  5AA 5  
5AA "C4'"  C4*  C 0 1 N N S 72.293 119.418 105.231 3.084  -1.257 0.084  "C4'"  5AA 6  
5AA "O4'"  O4*  O 0 1 N N N 73.112 119.955 106.298 3.266  0.101  -0.358 "O4'"  5AA 7  
5AA "C1'"  C1*  C 0 1 N N R 73.981 120.950 105.784 2.048  0.830  -0.103 "C1'"  5AA 8  
5AA N9     N9   N 0 1 Y N N 75.363 120.515 106.004 1.642  1.539  -1.318 N9     5AA 9  
5AA C4     C4   C 0 1 Y N N 76.382 121.258 106.553 1.019  2.752  -1.389 C4     5AA 10 
5AA N3     N3   N 0 1 Y N N 76.319 122.525 107.002 0.649  3.543  -0.371 N3     5AA 11 
5AA C2     C2   C 0 1 Y N N 77.503 122.919 107.468 0.058  4.665  -0.836 C2     5AA 12 
5AA N1     N1   N 0 1 Y N N 78.656 122.246 107.528 -0.176 5.034  -2.118 N1     5AA 13 
5AA C6     C6   C 0 1 Y N N 78.695 120.977 107.063 0.225  4.186  -3.096 C6     5AA 14 
5AA N6     N6   N 0 1 N N N 79.871 120.314 107.109 0.011  4.512  -4.446 N6     5AA 15 
5AA C5     C5   C 0 1 Y N N 77.493 120.437 106.551 0.848  2.993  -2.743 C5     5AA 16 
5AA N7     N7   N 0 1 Y N N 77.181 119.194 106.018 1.352  1.957  -3.488 N7     5AA 17 
5AA C8     C8   C 0 1 Y N N 75.912 119.294 105.707 1.821  1.102  -2.604 C8     5AA 18 
5AA C9     C9   C 0 1 N N N 80.098 118.955 106.633 0.437  3.609  -5.501 C9     5AA 19 
5AA C10    C10  C 0 1 N N N 81.076 120.929 107.644 -0.652 5.751  -4.811 C10    5AA 20 
5AA "C2'"  C2*  C 0 1 N N R 73.644 121.132 104.304 1.004  -0.169 0.402  "C2'"  5AA 21 
5AA "O2'"  O2*  O 0 1 N N N 72.694 122.169 104.162 0.908  -0.058 1.821  "O2'"  5AA 22 
5AA "C3'"  C3*  C 0 1 N N S 73.045 119.776 103.962 1.585  -1.511 -0.024 "C3'"  5AA 23 
5AA "N3'"  N3*  N 0 1 N N N 72.188 119.852 102.836 1.125  -2.643 0.762  "N3'"  5AA 24 
5AA OP1    O1P  O 0 1 N N N ?      ?       ?       7.838  -2.271 -1.140 OP1    5AA 25 
5AA HOP3   3HOP H 0 0 N N N 71.528 115.439 106.559 6.496  -3.019 -3.620 HOP3   5AA 26 
5AA HOP2   2HOP H 0 0 N N N 75.657 116.244 106.603 6.687  -4.939 -1.247 HOP2   5AA 27 
5AA "H5'"  1H5* H 0 1 N N N 71.446 117.762 106.372 3.679  -2.084 -1.817 "H5'"  5AA 28 
5AA "H5''" 2H5* H 0 0 N N N 71.388 117.504 104.702 3.787  -3.225 -0.451 "H5''" 5AA 29 
5AA "H4'"  H4*  H 0 1 N N N 71.261 119.836 105.167 3.424  -1.305 1.126  "H4'"  5AA 30 
5AA "H1'"  H1*  H 0 1 N N N 73.858 121.934 106.294 2.264  1.616  0.627  "H1'"  5AA 31 
5AA H2     H2   H 0 1 N N N 77.533 123.950 107.860 -0.275 5.368  -0.079 H2     5AA 32 
5AA H8     H8   H 0 1 N N N 75.370 118.450 105.249 2.297  0.157  -2.832 H8     5AA 33 
5AA H91    1H9  H 0 1 N N N 79.762 118.931 105.570 -0.188 2.713  -5.503 H91    5AA 34 
5AA H92    2H9  H 0 1 N N N 81.069 118.408 106.671 1.478  3.312  -5.346 H92    5AA 35 
5AA H93    3H9  H 0 1 N N N 79.349 118.309 107.148 0.354  4.100  -6.474 H93    5AA 36 
5AA H101   1H10 H 0 0 N N N 80.847 121.290 108.674 -1.703 5.717  -4.511 H101   5AA 37 
5AA H102   2H10 H 0 0 N N N 82.047 120.382 107.682 -0.599 5.904  -5.892 H102   5AA 38 
5AA H103   3H10 H 0 0 N N N 81.244 121.885 107.095 -0.171 6.597  -4.313 H103   5AA 39 
5AA "H2'"  H2*  H 0 1 N N N 74.503 121.413 103.651 0.001  0.002  -0.002 "H2'"  5AA 40 
5AA H1     H1   H 0 1 N N N 72.485 122.282 103.242 0.894  0.890  2.022  H1     5AA 41 
5AA "H3'"  H3*  H 0 1 N N N 73.806 119.013 103.675 1.326  -1.679 -1.077 "H3'"  5AA 42 
5AA "H3'1" 1H3* H 0 0 N N N 71.416 120.498 103.002 0.140  -2.791 0.854  "H3'1" 5AA 43 
5AA "H3'2" 2H3* H 0 0 N N N 72.693 120.093 101.983 1.785  -3.115 1.348  "H3'2" 5AA 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 
5AA P     OP3    SING N N 1  
5AA P     OP2    SING N N 2  
5AA P     "O5'"  SING N N 3  
5AA P     OP1    DOUB N N 4  
5AA OP3   HOP3   SING N N 5  
5AA OP2   HOP2   SING N N 6  
5AA "O5'" "C5'"  SING N N 7  
5AA "C5'" "C4'"  SING N N 8  
5AA "C5'" "H5'"  SING N N 9  
5AA "C5'" "H5''" SING N N 10 
5AA "C4'" "O4'"  SING N N 11 
5AA "C4'" "C3'"  SING N N 12 
5AA "C4'" "H4'"  SING N N 13 
5AA "O4'" "C1'"  SING N N 14 
5AA "C1'" N9     SING N N 15 
5AA "C1'" "C2'"  SING N N 16 
5AA "C1'" "H1'"  SING N N 17 
5AA N9    C4     SING Y N 18 
5AA N9    C8     SING Y N 19 
5AA C4    N3     SING Y N 20 
5AA C4    C5     DOUB Y N 21 
5AA N3    C2     DOUB Y N 22 
5AA C2    N1     SING Y N 23 
5AA C2    H2     SING N N 24 
5AA N1    C6     DOUB Y N 25 
5AA C6    N6     SING N N 26 
5AA C6    C5     SING Y N 27 
5AA N6    C9     SING N N 28 
5AA N6    C10    SING N N 29 
5AA C5    N7     SING Y N 30 
5AA N7    C8     DOUB Y N 31 
5AA C8    H8     SING N N 32 
5AA C9    H91    SING N N 33 
5AA C9    H92    SING N N 34 
5AA C9    H93    SING N N 35 
5AA C10   H101   SING N N 36 
5AA C10   H102   SING N N 37 
5AA C10   H103   SING N N 38 
5AA "C2'" "O2'"  SING N N 39 
5AA "C2'" "C3'"  SING N N 40 
5AA "C2'" "H2'"  SING N N 41 
5AA "O2'" H1     SING N N 42 
5AA "C3'" "N3'"  SING N N 43 
5AA "C3'" "H3'"  SING N N 44 
5AA "N3'" "H3'1" SING N N 45 
5AA "N3'" "H3'2" SING N 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 
5AA SMILES           ACDLabs              10.04 "O=P(O)(O)OCC3OC(n2cnc1c2ncnc1N(C)C)C(O)C3N"                                                                                                                            
5AA InChI            InChI                1.02b "InChI=1/C12H19N6O6P/c1-17(2)10-8-11(15-4-14-10)18(5-16-8)12-9(19)7(13)6(24-12)3-23-25(20,21)22/h4-7,9,12,19H,3,13H2,1-2H3,(H2,20,21,22)/t6-,7-,9-,12-/m1/s1/f/h20-21H" 
5AA InChIKey         InChI                1.02b BFPIKGKMRKBBBF-QDUKEEJXDN                                                                                                                                               
5AA SMILES_CANONICAL CACTVS               3.341 "CN(C)c1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](N)[C@H]3O"                                                                                                      
5AA SMILES           CACTVS               3.341 "CN(C)c1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(O)=O)[CH](N)[CH]3O"                                                                                                            
5AA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CN(C)c1c2c(ncn1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)N)O"                                                                                                    
5AA SMILES           "OpenEye OEToolkits" 1.5.0 "CN(C)c1c2c(ncn1)n(cn2)C3C(C(C(O3)COP(=O)(O)O)N)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 
5AA "SYSTEMATIC NAME" ACDLabs              10.04 
;3'-amino-3'-deoxy-N,N-dimethyladenosine 5'-(dihydrogen phosphate)
;
5AA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S,3S,4R,5R)-3-amino-5-(6-dimethylaminopurin-9-yl)-4-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
