data_DDG
# 
_chem_comp.id                                    DDG 
_chem_comp.name                                  "2',3'-DIDEOXY-GUANOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H14 N5 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               DG 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_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                        331.222 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     DDG 
_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        1QSS 
_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 
DDG OP3    O3P  O 0 1 N Y N 1.230  30.646 -6.035  -0.978 -1.712 5.736  OP3    DDG 1  
DDG P      P    P 0 1 N N N 0.613  29.229 -5.594  -0.499 -0.349 5.025  P      DDG 2  
DDG OP1    O1P  O 0 1 N N N 0.843  28.248 -6.683  -1.679 0.493  4.730  OP1    DDG 3  
DDG OP2    O2P  O 0 1 N N N 1.163  28.965 -4.244  0.497  0.446  6.006  OP2    DDG 4  
DDG "O5'"  O5*  O 0 1 N N N -0.967 29.472 -5.492  0.265  -0.700 3.652  "O5'"  DDG 5  
DDG "C5'"  C5*  C 0 1 N N N -1.466 30.421 -4.563  0.663  0.543  3.071  "C5'"  DDG 6  
DDG "C4'"  C4*  C 0 1 N N S -2.974 30.429 -4.564  1.400  0.279  1.757  "C4'"  DDG 7  
DDG "O4'"  O4*  O 0 1 N N N -3.475 31.155 -5.716  0.508  -0.298 0.776  "O4'"  DDG 8  
DDG "C3'"  C3*  C 0 1 N N N -3.649 29.072 -4.637  1.844  1.612  1.103  "C3'"  DDG 9  
DDG "C2'"  C2*  C 0 1 N N N -5.018 29.427 -5.207  1.957  1.220  -0.389 "C2'"  DDG 10 
DDG "C1'"  C1*  C 0 1 N N R -4.667 30.546 -6.185  1.087  -0.045 -0.514 "C1'"  DDG 11 
DDG N9     N9   N 0 1 Y N N -4.433 30.025 -7.529  0.027  0.173  -1.501 N9     DDG 12 
DDG C8     C8   C 0 1 Y N N -3.243 29.597 -8.072  -1.216 0.675  -1.251 C8     DDG 13 
DDG N7     N7   N 0 1 Y N N -3.367 29.153 -9.290  -1.898 0.734  -2.357 N7     DDG 14 
DDG C5     C5   C 0 1 Y N N -4.715 29.312 -9.576  -1.136 0.275  -3.380 C5     DDG 15 
DDG C6     C6   C 0 1 N N N -5.444 29.019 -10.757 -1.346 0.110  -4.769 C6     DDG 16 
DDG O6     O6   O 0 1 N N N -5.030 28.550 -11.823 -2.411 0.413  -5.280 O6     DDG 17 
DDG N1     N1   N 0 1 N N N -6.793 29.332 -10.613 -0.336 -0.386 -5.516 N1     DDG 18 
DDG C2     C2   C 0 1 N N N -7.367 29.864 -9.477  0.847  -0.727 -4.933 C2     DDG 19 
DDG N2     N2   N 0 1 N N N -8.691 30.100 -9.528  1.854  -1.235 -5.717 N2     DDG 20 
DDG N3     N3   N 0 1 N N N -6.697 30.145 -8.377  1.055  -0.579 -3.644 N3     DDG 21 
DDG C4     C4   C 0 1 Y N N -5.385 29.847 -8.497  0.103  -0.088 -2.842 C4     DDG 22 
DDG HOP3   3HOP H 0 0 N N N 1.082  31.274 -5.337  -1.430 -1.458 6.552  HOP3   DDG 23 
DDG HOP2   2HOP H 0 0 N N N 0.798  28.127 -3.983  1.250  -0.137 6.173  HOP2   DDG 24 
DDG "H5'"  1H5* H 0 1 N N N -1.054 30.252 -3.540  1.324  1.070  3.759  "H5'"  DDG 25 
DDG "H5''" 2H5* H 0 0 N N N -1.047 31.438 -4.747  -0.219 1.152  2.878  "H5''" DDG 26 
DDG "H4'"  H4*  H 0 1 N N N -3.219 30.895 -3.581  2.258  -0.371 1.923  "H4'"  DDG 27 
DDG "H3'1" 1H3* H 0 0 N N N -3.087 28.295 -5.207  2.809  1.935  1.495  "H3'1" DDG 28 
DDG "H3'2" 2H3* H 0 0 N N N -3.670 28.503 -3.678  1.089  2.386  1.246  "H3'2" DDG 29 
DDG "H2'"  1H2* H 0 1 N N N -5.584 28.573 -5.647  2.993  0.998  -0.648 "H2'"  DDG 30 
DDG "H2''" 2H2* H 0 0 N N N -5.794 29.685 -4.449  1.566  2.015  -1.023 "H2''" DDG 31 
DDG "H1'"  H1*  H 0 1 N N N -5.512 31.270 -6.240  1.705  -0.891 -0.815 "H1'"  DDG 32 
DDG H8     H8   H 0 1 N N N -2.261 29.608 -7.568  -1.580 0.979  -0.281 H8     DDG 33 
DDG H1     H1   H 0 1 N N N -7.411 29.157 -11.404 -0.457 -0.508 -6.471 H1     DDG 34 
DDG H21    1H2  H 0 1 N N N -9.115 30.493 -8.688  2.703  -1.478 -5.317 H21    DDG 35 
DDG H22    2H2  H 0 1 N N N -9.182 29.246 -9.793  1.714  -1.354 -6.669 H22    DDG 36 
# 
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 
DDG OP3   P      SING N N 1  
DDG OP3   HOP3   SING N N 2  
DDG P     OP1    DOUB N N 3  
DDG P     OP2    SING N N 4  
DDG P     "O5'"  SING N N 5  
DDG OP2   HOP2   SING N N 6  
DDG "O5'" "C5'"  SING N N 7  
DDG "C5'" "C4'"  SING N N 8  
DDG "C5'" "H5'"  SING N N 9  
DDG "C5'" "H5''" SING N N 10 
DDG "C4'" "O4'"  SING N N 11 
DDG "C4'" "C3'"  SING N N 12 
DDG "C4'" "H4'"  SING N N 13 
DDG "O4'" "C1'"  SING N N 14 
DDG "C3'" "C2'"  SING N N 15 
DDG "C3'" "H3'1" SING N N 16 
DDG "C3'" "H3'2" SING N N 17 
DDG "C2'" "C1'"  SING N N 18 
DDG "C2'" "H2'"  SING N N 19 
DDG "C2'" "H2''" SING N N 20 
DDG "C1'" N9     SING N N 21 
DDG "C1'" "H1'"  SING N N 22 
DDG N9    C8     SING Y N 23 
DDG N9    C4     SING Y N 24 
DDG C8    N7     DOUB Y N 25 
DDG C8    H8     SING N N 26 
DDG N7    C5     SING Y N 27 
DDG C5    C6     SING N N 28 
DDG C5    C4     DOUB Y N 29 
DDG C6    O6     DOUB N N 30 
DDG C6    N1     SING N N 31 
DDG N1    C2     SING N N 32 
DDG N1    H1     SING N N 33 
DDG C2    N2     SING N N 34 
DDG C2    N3     DOUB N N 35 
DDG N2    H21    SING N N 36 
DDG N2    H22    SING N N 37 
DDG N3    C4     SING N 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 
DDG SMILES           ACDLabs              10.04 "O=C1c2ncn(c2N=C(N)N1)C3OC(CC3)COP(=O)(O)O"                                                                                                                     
DDG InChI            InChI                1.02b "InChI=1/C10H14N5O6P/c11-10-13-8-7(9(16)14-10)12-4-15(8)6-2-1-5(21-6)3-20-22(17,18)19/h4-6H,1-3H2,(H2,17,18,19)(H3,11,13,14,16)/t5-,6+/m0/s1/f/h14,17-18H,11H2" 
DDG InChIKey         InChI                1.02b SDMRBYKCQICSIT-KZJATLAWDC                                                                                                                                       
DDG SMILES_CANONICAL CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@H]3CC[C@@H](CO[P](O)(O)=O)O3"                                                                                                          
DDG SMILES           CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3CC[CH](CO[P](O)(O)=O)O3"                                                                                                             
DDG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3CC[C@H](O3)COP(=O)(O)O)N=C(NC2=O)N"                                                                                                             
DDG SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3CCC(O3)COP(=O)(O)O)N=C(NC2=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 
DDG "SYSTEMATIC NAME" ACDLabs              10.04 "[(2S,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate" 
DDG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate"                      
# 
