data_4PE
# 
_chem_comp.id                                    4PE 
_chem_comp.name                                  "3-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-6-METHYL-3H-PYRROLO[2,3-D]PYRIMIDIN-2-OL" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C12 H16 N3 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               DC 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-04-18 
_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                        345.245 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     4PE 
_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        ? 
_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 
4PE P      P    P 0 1 N N N 2.195  1.583  -9.575  -3.967 -1.666 3.119  P      4PE 1  
4PE OP1    O1P  O 0 1 N N N 2.293  3.087  -9.497  -4.406 -2.599 4.209  OP1    4PE 2  
4PE OP2    O2P  O 0 1 N N N 2.270  0.865  -10.900 -3.912 -2.311 1.637  OP2    4PE 3  
4PE "O5'"  O5*  O 0 1 N N N 0.857  1.117  -8.770  -2.493 -1.028 3.315  "O5'"  4PE 4  
4PE "C5'"  C5*  C 0 1 N N N 0.391  -0.206 -8.998  -2.005 -0.136 2.327  "C5'"  4PE 5  
4PE "C4'"  C4*  C 0 1 N N R -0.781 -0.610 -8.082  -0.611 0.328  2.728  "C4'"  4PE 6  
4PE "O4'"  O4*  O 0 1 N N N -0.331 -0.567 -6.701  0.247  -0.829 2.764  "O4'"  4PE 7  
4PE "C3'"  C3*  C 0 1 N N S -2.041 0.263  -8.176  0.008  1.286  1.720  "C3'"  4PE 8  
4PE "O3'"  O3*  O 0 1 N N N -3.197 -0.542 -7.899  0.965  2.121  2.368  "O3'"  4PE 9  
4PE "C2'"  C2*  C 0 1 N N N -1.876 1.206  -7.008  0.710  0.360  0.754  "C2'"  4PE 10 
4PE "C1'"  C1*  C 0 1 N N R -1.249 0.280  -5.977  1.157  -0.778 1.657  "C1'"  4PE 11 
4PE N1     N1   N 0 1 Y N N -0.569 1.017  -4.908  1.164  -2.047 0.989  N1     4PE 12 
4PE C2     C2   C 0 1 Y N N -1.139 1.148  -3.652  2.300  -2.578 0.367  C2     4PE 13 
4PE O2     O2   O 0 1 N N N -2.364 0.623  -3.500  3.435  -1.828 0.419  O2     4PE 14 
4PE N3     N3   N 0 1 Y N N -0.647 1.726  -2.605  2.387  -3.719 -0.259 N3     4PE 15 
4PE C5     C5   C 0 1 Y N N 1.264  2.256  -4.095  -0.003 -3.989 0.324  C5     4PE 16 
4PE C6     C6   C 0 1 Y N N 0.672  1.622  -5.104  0.004  -2.810 0.941  C6     4PE 17 
4PE C14    C14  C 0 1 Y N N 2.470  2.972  -3.867  -0.942 -5.023 0.066  C14    4PE 18 
4PE C15    C15  C 0 1 Y N N 2.435  3.308  -2.561  -0.254 -5.951 -0.630 C15    4PE 19 
4PE C16    C16  C 0 1 N N N 3.475  4.088  -1.832  -0.797 -7.238 -1.142 C16    4PE 20 
4PE N17    N17  N 0 1 Y N N 1.291  2.888  -1.870  1.087  -5.637 -0.872 N17    4PE 21 
4PE C4     C4   C 0 1 Y N N 0.585  2.277  -2.788  1.241  -4.469 -0.306 C4     4PE 22 
4PE OP3    O3P  O 0 1 N Y N ?      ?      ?       -4.901 -0.360 2.920  OP3    4PE 23 
4PE HOP2   2HOP H 0 0 N N N 1.392  0.714  -11.229 -4.684 -2.823 1.313  HOP2   4PE 24 
4PE "H5'"  1H5* H 0 1 N N N 1.226  -0.888 -8.780  -1.970 -0.654 1.366  "H5'"  4PE 25 
4PE "H5''" 2H5* H 0 0 N N N 0.050  -0.274 -10.042 -2.682 0.718  2.254  "H5''" 4PE 26 
4PE "H4'"  H4*  H 0 1 N N N -1.072 -1.613 -8.426  -0.644 0.754  3.736  "H4'"  4PE 27 
4PE "H3'"  H3*  H 0 1 N N N -2.160 0.745  -9.158  -0.723 1.941  1.237  "H3'"  4PE 28 
4PE "HO3'" H3T  H 0 0 N Y N -2.941 -1.455 -7.838  0.479  2.685  2.995  "HO3'" 4PE 29 
4PE "H2'"  1H2* H 0 1 N N N -2.811 1.682  -6.677  -0.002 -0.001 0.002  "H2'"  4PE 30 
4PE "H2''" 2H2* H 0 0 N N N -1.231 2.064  -7.249  1.556  0.819  0.233  "H2''" 4PE 31 
4PE "H1'"  H1*  H 0 1 N N N -2.025 -0.312 -5.469  2.154  -0.576 2.064  "H1'"  4PE 32 
4PE H2     H2   H 0 1 N N N -2.301 -0.324 -3.464  3.224  -0.882 0.417  H2     4PE 33 
4PE H6     H6   H 0 1 N N N 1.151  1.576  -6.071  -0.868 -2.390 1.426  H6     4PE 34 
4PE H14    H14  H 0 1 N N N 3.246  3.198  -4.583  -1.975 -5.051 0.365  H14    4PE 35 
4PE H161   1H16 H 0 0 N N N 4.393  4.129  -2.436  -1.217 -7.821 -0.321 H161   4PE 36 
4PE H162   2H16 H 0 0 N N N 3.690  3.601  -0.869  -0.003 -7.817 -1.619 H162   4PE 37 
4PE H163   3H16 H 0 0 N N N 3.109  5.110  -1.652  -1.579 -7.048 -1.880 H163   4PE 38 
4PE HOP3   3HOP H 0 0 N N N -0.062 -0.947 -0.049  -5.874 -0.475 2.871  HOP3   4PE 39 
# 
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 
4PE P     OP1    DOUB N N 1  
4PE P     OP2    SING N N 2  
4PE P     "O5'"  SING N N 3  
4PE P     OP3    SING N N 4  
4PE OP2   HOP2   SING N N 5  
4PE "O5'" "C5'"  SING N N 6  
4PE "C5'" "C4'"  SING N N 7  
4PE "C5'" "H5'"  SING N N 8  
4PE "C5'" "H5''" SING N N 9  
4PE "C4'" "O4'"  SING N N 10 
4PE "C4'" "C3'"  SING N N 11 
4PE "C4'" "H4'"  SING N N 12 
4PE "O4'" "C1'"  SING N N 13 
4PE "C3'" "O3'"  SING N N 14 
4PE "C3'" "C2'"  SING N N 15 
4PE "C3'" "H3'"  SING N N 16 
4PE "O3'" "HO3'" SING N N 17 
4PE "C2'" "C1'"  SING N N 18 
4PE "C2'" "H2'"  SING N N 19 
4PE "C2'" "H2''" SING N N 20 
4PE "C1'" N1     SING N N 21 
4PE "C1'" "H1'"  SING N N 22 
4PE N1    C2     SING Y N 23 
4PE N1    C6     SING Y N 24 
4PE C2    O2     SING N N 25 
4PE C2    N3     DOUB Y N 26 
4PE O2    H2     SING N N 27 
4PE N3    C4     SING Y N 28 
4PE C5    C6     DOUB Y N 29 
4PE C5    C14    SING Y N 30 
4PE C5    C4     SING Y N 31 
4PE C6    H6     SING N N 32 
4PE C14   C15    DOUB Y N 33 
4PE C14   H14    SING N N 34 
4PE C15   C16    SING N N 35 
4PE C15   N17    SING Y N 36 
4PE C16   H161   SING N N 37 
4PE C16   H162   SING N N 38 
4PE C16   H163   SING N N 39 
4PE N17   C4     DOUB Y N 40 
4PE OP3   HOP3   SING N N 41 
# 
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 
4PE SMILES           ACDLabs              10.04 "O=P(O)(O)OCC3OC(N2C(=NC1=NC(=CC1=C2)C)O)CC3O"                                                                                                                         
4PE InChI            InChI                1.02b "InChI=1/C12H16N3O7P/c1-6-2-7-4-15(12(17)14-11(7)13-6)10-3-8(16)9(22-10)5-21-23(18,19)20/h2,4,8-10,16H,3,5H2,1H3,(H,13,14,17)(H2,18,19,20)/t8-,9+,10+/m0/s1/f/h17-19H" 
4PE InChIKey         InChI                1.02b VOKZMFPBFFRNPZ-RFESXZNQDE                                                                                                                                              
4PE SMILES_CANONICAL CACTVS               3.341 "Cc1cc2cn([C@H]3C[C@H](O)[C@@H](CO[P](O)(O)=O)O3)c(O)nc2n1"                                                                                                            
4PE SMILES           CACTVS               3.341 "Cc1cc2cn([CH]3C[CH](O)[CH](CO[P](O)(O)=O)O3)c(O)nc2n1"                                                                                                                
4PE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1cc-2cn(c(nc2n1)O)[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O"                                                                                                             
4PE SMILES           "OpenEye OEToolkits" 1.5.0 "Cc1cc-2cn(c(nc2n1)O)C3CC(C(O3)COP(=O)(O)O)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 
4PE "SYSTEMATIC NAME" ACDLabs              10.04 "3-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-6-methyl-3H-pyrrolo[2,3-d]pyrimidin-2-ol"                 
4PE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-3-hydroxy-5-(2-hydroxy-6-methyl-pyrrolo[2,3-d]pyrimidin-3-yl)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
