data_APN
# 
_chem_comp.id                                    APN 
_chem_comp.name                                  2-AMINOETHYLGLYCINE-CARBONYLMETHYLENE-ADENINE 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H16 N7 O3" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        294.290 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     APN 
_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        176D 
_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 
APN "C8'"  "C8'"  C 0 1 N N N 3.043  8.282  -3.822 -0.222 -0.296 -1.117 "C8'"  APN 1  
APN "C7'"  "C7'"  C 0 1 N N N 3.943  8.235  -2.569 -1.067 0.422  -0.097 "C7'"  APN 2  
APN "O7'"  "O7'"  O 0 1 N N N 4.777  7.331  -2.505 -0.548 1.171  0.703  "O7'"  APN 3  
APN "C5'"  "C5'"  C 0 1 N N N 4.921  9.326  -0.585 -3.015 -0.761 -0.959 "C5'"  APN 4  
APN "C'"   "C'"   C 0 1 N N N 4.397  9.519  0.842  -3.168 -2.067 -0.221 "C'"   APN 5  
APN "O1'"  "O1'"  O 0 1 N N N 4.441  10.621 1.383  -2.719 -2.186 0.894  "O1'"  APN 6  
APN OXT    OXT    O 0 1 N Y N 3.864  8.439  1.423  -3.802 -3.096 -0.803 OXT    APN 7  
APN "N4'"  "N4'"  N 0 1 N N N 3.849  9.187  -1.602 -2.401 0.231  -0.073 "N4'"  APN 8  
APN "C3'"  "C3'"  C 0 1 N N N 2.692  10.103 -1.481 -3.238 1.016  0.838  "C3'"  APN 9  
APN "C2'"  "C2'"  C 0 1 N N N 2.971  11.548 -1.936 -3.691 2.299  0.137  "C2'"  APN 10 
APN "N1'"  "N1'"  N 1 1 N N N 3.258  11.582 -3.359 -4.529 3.086  1.051  "N1'"  APN 11 
APN N9     N9     N 0 1 Y N N 2.122  7.128  -3.984 1.166  0.161  -1.010 N9     APN 12 
APN C8     C8     C 0 1 Y N N 1.960  6.368  -5.117 1.750  1.147  -1.749 C8     APN 13 
APN N7     N7     N 0 1 Y N N 1.025  5.467  -5.034 2.993  1.293  -1.392 N7     APN 14 
APN C5     C5     C 0 1 Y N N 0.517  5.627  -3.744 3.283  0.417  -0.400 C5     APN 15 
APN C6     C6     C 0 1 Y N N -0.495 4.954  -2.997 4.434  0.120  0.350  C6     APN 16 
APN N6     N6     N 0 1 N N N -1.188 3.908  -3.455 5.614  0.811  0.141  N6     APN 17 
APN N1     N1     N 0 1 Y N N -0.768 5.366  -1.736 4.360  -0.838 1.269  N1     APN 18 
APN C2     C2     C 0 1 Y N N -0.080 6.398  -1.233 3.238  -1.503 1.475  C2     APN 19 
APN N3     N3     N 0 1 Y N N 0.903  7.101  -1.819 2.139  -1.263 0.793  N3     APN 20 
APN C4     C4     C 0 1 Y N N 1.171  6.659  -3.096 2.116  -0.323 -0.147 C4     APN 21 
APN "H8'1" "1H8'" H 0 0 N N N 3.726  8.275  -4.666 -0.599 -0.082 -2.117 "H8'1" APN 22 
APN "H8'2" "2H8'" H 0 0 N N N 2.460  9.184  -3.939 -0.265 -1.370 -0.934 "H8'2" APN 23 
APN "H5'1" "1H5'" H 0 0 N N N 5.526  10.189 -0.849 -3.996 -0.407 -1.277 "H5'1" APN 24 
APN "H5'2" "2H5'" H 0 0 N N N 5.589  8.462  -0.560 -2.381 -0.910 -1.833 "H5'2" APN 25 
APN HXT    HXT    H 0 1 N N N 3.539  8.558  2.307  -3.900 -3.934 -0.330 HXT    APN 26 
APN "H3'1" "1H3'" H 0 0 N N N 2.356  10.159 -0.449 -4.111 0.431  1.125  "H3'1" APN 27 
APN "H3'2" "2H3'" H 0 0 N N N 1.830  9.729  -2.031 -2.663 1.273  1.729  "H3'2" APN 28 
APN "H2'1" "1H2'" H 0 0 N N N 3.814  11.968 -1.384 -2.817 2.884  -0.150 "H2'1" APN 29 
APN "H2'2" "2H2'" H 0 0 N N N 2.085  12.147 -1.719 -4.265 2.042  -0.753 "H2'2" APN 30 
APN "H1'1" "1H1'" H 0 0 N N N 3.557  10.705 -3.754 -5.338 2.544  1.317  "H1'1" APN 31 
APN "H1'2" "2H1'" H 0 0 N N N 4.019  10.950 -3.608 -3.998 3.323  1.875  "H1'2" APN 32 
APN "H1'3" "3H1'" H 0 0 N N N 2.515  11.147 -3.907 -4.828 3.932  0.589  "H1'3" APN 33 
APN H8     H8     H 0 1 N N N 2.548  6.509  -6.006 1.254  1.721  -2.518 H8     APN 34 
APN HN61   1HN6   H 0 0 N N N -1.051 3.611  -4.410 6.400  0.599  0.668  HN61   APN 35 
APN HN62   2HN6   H 0 0 N N N -1.875 3.461  -2.860 5.656  1.506  -0.535 HN62   APN 36 
APN H2     H2     H 0 1 N N N -0.380 6.708  -0.247 3.223  -2.274 2.231  H2     APN 37 
# 
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 
APN "C8'" "C7'"  SING N N 1  
APN "C8'" N9     SING N N 2  
APN "C8'" "H8'1" SING N N 3  
APN "C8'" "H8'2" SING N N 4  
APN "C7'" "O7'"  DOUB N N 5  
APN "C7'" "N4'"  SING N N 6  
APN "C5'" "C'"   SING N N 7  
APN "C5'" "N4'"  SING N N 8  
APN "C5'" "H5'1" SING N N 9  
APN "C5'" "H5'2" SING N N 10 
APN "C'"  "O1'"  DOUB N N 11 
APN "C'"  OXT    SING N N 12 
APN OXT   HXT    SING N N 13 
APN "N4'" "C3'"  SING N N 14 
APN "C3'" "C2'"  SING N N 15 
APN "C3'" "H3'1" SING N N 16 
APN "C3'" "H3'2" SING N N 17 
APN "C2'" "N1'"  SING N N 18 
APN "C2'" "H2'1" SING N N 19 
APN "C2'" "H2'2" SING N N 20 
APN "N1'" "H1'1" SING N N 21 
APN "N1'" "H1'2" SING N N 22 
APN "N1'" "H1'3" SING N N 23 
APN N9    C8     SING Y N 24 
APN N9    C4     SING Y N 25 
APN C8    N7     DOUB Y N 26 
APN C8    H8     SING N N 27 
APN N7    C5     SING Y N 28 
APN C5    C6     SING Y N 29 
APN C5    C4     DOUB Y N 30 
APN C6    N6     SING N N 31 
APN C6    N1     DOUB Y N 32 
APN N6    HN61   SING N N 33 
APN N6    HN62   SING N N 34 
APN N1    C2     SING Y N 35 
APN C2    N3     DOUB Y N 36 
APN C2    H2     SING N N 37 
APN N3    C4     SING Y N 38 
# 
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 
APN SMILES           ACDLabs              10.04 "O=C(O)CN(C(=O)Cn1c2ncnc(c2nc1)N)CC[NH3+]"                                                                                                              
APN InChI            InChI                1.02b "InChI=1/C11H15N7O3/c12-1-2-17(4-8(20)21)7(19)3-18-6-16-9-10(13)14-5-15-11(9)18/h5-6H,1-4,12H2,(H,20,21)(H2,13,14,15)/p+1/fC11H16N7O3/h12,20H,13H2/q+1" 
APN InChIKey         InChI                1.02b DUMWERDMQQCWPO-UJNBOMDVCC                                                                                                                               
APN SMILES_CANONICAL CACTVS               3.341 "Nc1ncnc2n(CC(=O)N(CC[NH3+])CC(O)=O)cnc12"                                                                                                              
APN SMILES           CACTVS               3.341 "Nc1ncnc2n(CC(=O)N(CC[NH3+])CC(O)=O)cnc12"                                                                                                              
APN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)CC(=O)N(CC[NH3+])CC(=O)O)N"                                                                                                          
APN SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)CC(=O)N(CC[NH3+])CC(=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 
APN "SYSTEMATIC NAME" ACDLabs              10.04 "2-{[(6-amino-9H-purin-9-yl)acetyl](carboxymethyl)amino}ethanaminium" 
APN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[2-(6-aminopurin-9-yl)ethanoyl-(carboxymethyl)amino]ethylazanium"  
# 
