data_LCG
# 
_chem_comp.id                                    LCG 
_chem_comp.name                                  "[(1R,3R,4R,7S)-7-HYDROXY-3-(GUANIN-9-YL)-2,5-DIOXABICYCLO[2.2.1]HEPT-1-YL]METHYL DIHYDROGEN PHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H14 N5 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               DG 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-06-27 
_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                        375.231 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     LCG 
_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        1H0Q 
_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 
LCG P      P    P 0 1 N N N -3.891 -2.803 5.998  -0.875 -0.421 4.967  P      LCG 1  
LCG OP1    O1P  O 0 1 N N N -3.951 -1.905 7.172  -2.171 0.235  4.681  OP1    LCG 2  
LCG "O5'"  O5*  O 0 1 N N N -2.350 -3.199 5.735  -0.131 -0.765 3.581  "O5'"  LCG 3  
LCG "C5'"  C5*  C 0 1 N N N -1.458 -3.515 6.788  0.068  0.475  2.901  "C5'"  LCG 4  
LCG "C3'"  C3*  C 0 1 N N S 0.543  -2.751 5.353  1.110  1.467  0.675  "C3'"  LCG 5  
LCG "C6'"  C6*  C 0 1 N N N 1.036  -4.135 7.189  2.200  -0.414 1.649  "C6'"  LCG 6  
LCG N9     N9   N 0 1 Y N N 0.621  -4.660 3.005  -0.218 -0.007 -1.666 N9     LCG 7  
LCG C8     C8   C 0 1 Y N N -0.581 -4.331 2.417  -1.343 0.730  -1.438 C8     LCG 8  
LCG C4     C4   C 0 1 Y N N 1.498  -4.820 1.957  -0.140 -0.231 -3.014 C4     LCG 9  
LCG N7     N7   N 0 1 Y N N -0.544 -4.300 1.115  -1.952 0.966  -2.563 N7     LCG 10 
LCG C5     C5   C 0 1 Y N N 0.771  -4.627 0.803  -1.256 0.396  -3.577 C5     LCG 11 
LCG C6     C6   C 0 1 N N N 1.413  -4.777 -0.469 -1.436 0.327  -4.979 C6     LCG 12 
LCG "C2'"  C2*  C 0 1 N N R 1.703  -3.696 5.061  1.839  0.600  -0.416 "C2'"  LCG 13 
LCG O6     O6   O 0 1 N N N 0.924  -4.659 -1.590 -2.394 0.860  -5.512 O6     LCG 14 
LCG "C4'"  C4*  C 0 1 N N R -0.095 -3.864 6.178  0.775  0.218  1.569  "C4'"  LCG 15 
LCG "C1'"  C1*  C 0 1 N N R 0.963  -4.885 4.435  0.732  -0.473 -0.654 "C1'"  LCG 16 
LCG C2     C2   C 0 1 N N N 3.420  -5.262 0.850  0.546  -0.935 -5.104 C2     LCG 17 
LCG N1     N1   N 0 1 N N N 2.763  -5.106 -0.353 -0.517 -0.338 -5.712 N1     LCG 18 
LCG "O4'"  O4*  O 0 1 N N N -0.183 -4.968 5.272  0.071  -0.629 0.617  "O4'"  LCG 19 
LCG OP2    O2P  O 0 1 N N N -4.472 -2.368 4.709  -1.133 -1.781 5.789  OP2    LCG 20 
LCG N2     N2   N 0 1 N N N 4.718  -5.551 0.790  1.460  -1.610 -5.873 N2     LCG 21 
LCG N3     N3   N 0 1 N N N 2.823  -5.135 2.047  0.725  -0.878 -3.803 N3     LCG 22 
LCG "O2'"  O2*  O 0 1 N N N 2.184  -4.110 6.342  2.830  -0.094 0.393  "O2'"  LCG 23 
LCG "O3'"  O3*  O 0 1 N N N 0.909  -1.588 6.085  1.991  2.387  1.324  "O3'"  LCG 24 
LCG OP3    O3P  O 0 1 N Y N -4.586 -4.199 6.407  0.046  0.567  5.841  OP3    LCG 25 
LCG "H5'"  1H5* H 0 1 N N N -1.835 -4.366 7.355  -0.896 0.947  2.715  "H5'"  LCG 26 
LCG "H5''" 2H5* H 0 0 N N N -1.351 -2.655 7.449  0.681  1.133  3.517  "H5''" LCG 27 
LCG "H3'"  H3*  H 0 1 N N N -0.050 -2.509 4.469  0.215  1.958  0.291  "H3'"  LCG 28 
LCG "H6'1" 1H6* H 0 0 N N N 0.928  -5.075 7.741  2.761  0.021  2.475  "H6'1" LCG 29 
LCG "H6'2" 2H6* H 0 0 N N N 1.099  -3.316 7.906  2.127  -1.495 1.770  "H6'2" LCG 30 
LCG H8     H8   H 0 1 N N N -1.497 -4.127 2.955  -1.679 1.067  -0.468 H8     LCG 31 
LCG "H2'"  1H2* H 0 1 N N N 2.475  -3.281 4.415  2.216  1.129  -1.292 "H2'"  LCG 32 
LCG "H1'"  H1*  H 0 1 N N N 1.569  -5.791 4.496  1.181  -1.417 -0.964 "H1'"  LCG 33 
LCG H1     H1   H 0 1 N N N 3.279  -5.235 -1.211 -0.620 -0.399 -6.674 H1     LCG 34 
LCG HOP2   2HOP H 0 0 N N N -4.433 -2.945 3.955  -1.580 -1.531 6.610  HOP2   LCG 35 
LCG H21    1H2  H 0 1 N N N 5.180  -5.637 -0.108 2.225  -2.036 -5.456 H21    LCG 36 
LCG H22    2H2  H 0 1 N N N 5.229  -5.684 1.649  1.340  -1.664 -6.834 H22    LCG 37 
LCG "HO3'" H3T  H 0 0 N Y N 1.306  -0.895 5.571  2.325  2.983  0.640  "HO3'" LCG 38 
LCG HOP3   3HOP H 0 0 N N N -4.547 -4.776 5.653  0.878  0.102  6.004  HOP3   LCG 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 
LCG P     OP1    DOUB N N 1  
LCG P     "O5'"  SING N N 2  
LCG P     OP2    SING N N 3  
LCG P     OP3    SING N N 4  
LCG "O5'" "C5'"  SING N N 5  
LCG "C5'" "C4'"  SING N N 6  
LCG "C5'" "H5'"  SING N N 7  
LCG "C5'" "H5''" SING N N 8  
LCG "C3'" "C2'"  SING N N 9  
LCG "C3'" "C4'"  SING N N 10 
LCG "C3'" "O3'"  SING N N 11 
LCG "C3'" "H3'"  SING N N 12 
LCG "C6'" "C4'"  SING N N 13 
LCG "C6'" "O2'"  SING N N 14 
LCG "C6'" "H6'1" SING N N 15 
LCG "C6'" "H6'2" SING N N 16 
LCG N9    C8     SING Y N 17 
LCG N9    C4     SING Y N 18 
LCG N9    "C1'"  SING N N 19 
LCG C8    N7     DOUB Y N 20 
LCG C8    H8     SING N N 21 
LCG C4    C5     DOUB Y N 22 
LCG C4    N3     SING N N 23 
LCG N7    C5     SING Y N 24 
LCG C5    C6     SING N N 25 
LCG C6    O6     DOUB N N 26 
LCG C6    N1     SING N N 27 
LCG "C2'" "C1'"  SING N N 28 
LCG "C2'" "O2'"  SING N N 29 
LCG "C2'" "H2'"  SING N N 30 
LCG "C4'" "O4'"  SING N N 31 
LCG "C1'" "O4'"  SING N N 32 
LCG "C1'" "H1'"  SING N N 33 
LCG C2    N1     SING N N 34 
LCG C2    N2     SING N N 35 
LCG C2    N3     DOUB N N 36 
LCG N1    H1     SING N N 37 
LCG OP2   HOP2   SING N N 38 
LCG N2    H21    SING N N 39 
LCG N2    H22    SING N N 40 
LCG "O3'" "HO3'" SING N N 41 
LCG OP3   HOP3   SING N N 42 
# 
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 
LCG SMILES           ACDLabs              10.04 "O=C2NC(=Nc1n(cnc12)C4OC3(C(O)C4OC3)COP(=O)(O)O)N"                                                                                                                                       
LCG InChI            InChI                1.02b "InChI=1/C11H14N5O8P/c12-10-14-7-4(8(18)15-10)13-3-16(7)9-5-6(17)11(24-9,1-22-5)2-23-25(19,20)21/h3,5-6,9,17H,1-2H2,(H2,19,20,21)(H3,12,14,15,18)/t5-,6+,9-,11-/m1/s1/f/h15,19-20H,12H2" 
LCG InChIKey         InChI                1.02b FZGXOAHULCKQGE-SQOYIHLFDE                                                                                                                                                                
LCG SMILES_CANONICAL CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@]4(CO[C@@H]3[C@@H]4O)CO[P](O)(O)=O"                                                                                                                     
LCG SMILES           CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[C]4(CO[CH]3[CH]4O)CO[P](O)(O)=O"                                                                                                                            
LCG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@H]4[C@@H]([C@@](O3)(CO4)COP(=O)(O)O)O)N=C(NC2=O)N"                                                                                                                    
LCG SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C4C(C(O3)(CO4)COP(=O)(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 
LCG "SYSTEMATIC NAME" ACDLabs              10.04 "2-amino-9-{2,5-anhydro-4-[(phosphonooxy)methyl]-alpha-L-lyxofuranosyl}-1,9-dihydro-6H-purin-6-one"                       
LCG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R,4R,6R,7S)-6-(2-amino-6-oxo-1H-purin-9-yl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-4-yl]methyl dihydrogen phosphate" 
# 
