data_G2L
# 
_chem_comp.id                                    G2L 
_chem_comp.name                                  "3'-O-METHYOXYETHYL-GUANOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C13 H20 N5 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               G 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-10-29 
_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                        421.300 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     G2L 
_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 
G2L OP3    O3P  O 0 1 N Y N ?      ?       ?      6.456  2.538  -1.495 OP3    G2L 1  
G2L P      P    P 0 1 N N N 4.834  -9.721  5.263  6.145  3.523  -0.251 P      G2L 2  
G2L OP1    O1P  O 0 1 N N N 4.062  -10.982 5.330  6.560  4.952  -0.444 OP1    G2L 3  
G2L OP2    O2P  O 0 1 N N N 5.865  -9.569  4.213  6.843  2.773  1.000  OP2    G2L 4  
G2L "O5'"  O5*  O 0 1 N N N 3.798  -8.479  5.126  4.566  3.301  0.029  "O5'"  G2L 5  
G2L "C5'"  C5*  C 0 1 N N N 2.435  -8.514  5.515  4.092  1.980  0.223  "C5'"  G2L 6  
G2L "C4'"  C4*  C 0 1 N N R 1.511  -8.245  4.306  2.595  2.031  0.465  "C4'"  G2L 7  
G2L "O4'"  O4*  O 0 1 N N N 1.618  -6.905  3.847  1.933  2.574  -0.689 "O4'"  G2L 8  
G2L "C3'"  C3*  C 0 1 N N S 1.730  -9.174  3.099  1.969  0.663  0.677  "C3'"  G2L 9  
G2L "O3'"  O3*  O 0 1 N N N 0.808  -10.256 3.040  2.143  0.197  1.998  "O3'"  G2L 10 
G2L "C2'"  C2*  C 0 1 N N R 1.487  -8.249  1.904  0.518  0.913  0.310  "C2'"  G2L 11 
G2L "O2'"  O2*  O 0 1 N N N 0.103  -8.197  1.562  -0.210 1.445  1.415  "O2'"  G2L 12 
G2L "C1'"  C1*  C 0 1 N N R 1.791  -6.863  2.432  0.622  1.976  -0.784 "C1'"  G2L 13 
G2L N9     N9   N 0 1 Y N N 3.127  -6.284  2.162  0.424  1.450  -2.136 N9     G2L 14 
G2L C8     C8   C 0 1 Y N N 4.357  -6.708  2.570  1.394  0.902  -2.941 C8     G2L 15 
G2L N7     N7   N 0 1 Y N N 5.356  -5.975  2.164  0.919  0.513  -4.107 N7     G2L 16 
G2L C5     C5   C 0 1 Y N N 4.743  -4.972  1.421  -0.407 0.825  -4.042 C5     G2L 17 
G2L C6     C6   C 0 1 N N N 5.307  -3.858  0.716  -1.426 0.627  -5.035 C6     G2L 18 
G2L O6     O6   O 0 1 N N N 6.488  -3.530  0.611  -1.220 0.122  -6.132 O6     G2L 19 
G2L N1     N1   N 0 1 N N N 4.334  -3.083  0.088  -2.667 1.088  -4.574 N1     G2L 20 
G2L C2     C2   C 0 1 N N N 2.978  -3.352  0.136  -2.902 1.672  -3.307 C2     G2L 21 
G2L N2     N2   N 0 1 N N N 2.172  -2.522  -0.515 -4.197 2.052  -3.067 N2     G2L 22 
G2L N3     N3   N 0 1 N N N 2.443  -4.388  0.797  -1.949 1.842  -2.416 N3     G2L 23 
G2L C4     C4   C 0 1 Y N N 3.376  -5.160  1.417  -0.743 1.403  -2.842 C4     G2L 24 
G2L "CA'"  CA*  C 0 1 N N N 1.089  -11.349 3.893  1.460  -1.029 2.206  "CA'"  G2L 25 
G2L "CB'"  CB*  C 0 1 N N N -0.008 -12.398 3.702  1.700  -1.494 3.629  "CB'"  G2L 26 
G2L "OC'"  OC*  O 0 1 N N N 0.108  -12.985 2.416  3.094  -1.697 3.822  "OC'"  G2L 27 
G2L "CD'"  CD*  C 0 1 N N N -0.895 -13.954 2.173  3.381  -2.113 5.150  "CD'"  G2L 28 
G2L HOP3   3HOP H 0 0 N N N 0.496  0.809   -0.043 7.351  2.548  -1.896 HOP3   G2L 29 
G2L HOP2   2HOP H 0 0 N N N 6.246  -10.334 4.627  7.814  2.842  1.113  HOP2   G2L 30 
G2L "H5'"  1H5* H 0 1 N N N 2.185  -9.470  5.969  4.308  1.388  -0.668 "H5'"  G2L 31 
G2L "H5''" 2H5* H 0 0 N N N 2.271  -7.734  6.259  4.597  1.541  1.085  "H5''" G2L 32 
G2L "H4'"  H4*  H 0 1 N N N 0.481  -8.368  4.640  2.399  2.693  1.317  "H4'"  G2L 33 
G2L "H3'"  H3*  H 0 1 N N N 2.758  -9.531  3.054  2.403  -0.065 -0.019 "H3'"  G2L 34 
G2L "H2'"  H2*  H 0 1 N N N 2.150  -8.485  1.073  -0.000 0.001  -0.003 "H2'"  G2L 35 
G2L "HO2'" 2HO* H 0 0 N N N -0.048 -7.623  0.820  -1.062 1.768  1.071  "HO2'" G2L 36 
G2L "H1'"  H1*  H 0 1 N N N 1.056  -6.173  2.019  -0.125 2.769  -0.673 "H1'"  G2L 37 
G2L H8     H8   H 0 1 N N N 4.466  -7.580  3.175  2.424  0.815  -2.621 H8     G2L 38 
G2L H1     H1   H 0 1 N N N 4.659  -2.277  -0.429 -3.462 0.996  -5.200 H1     G2L 39 
G2L H21    1H2  H 0 1 N N N 1.176  -2.684  -0.503 -4.355 2.854  -2.502 H21    G2L 40 
G2L H22    2H2  H 0 1 N N N 2.558  -1.732  -1.019 -4.928 1.510  -3.467 H22    G2L 41 
G2L "HA'1" 1HA* H 0 0 N N N 2.058  -11.781 3.645  0.394  -0.862 2.020  "HA'1" G2L 42 
G2L "HA'2" 2HA* H 0 0 N N N 1.084  -11.023 4.932  1.848  -1.762 1.493  "HA'2" G2L 43 
G2L "HB'1" 1HB* H 0 0 N N N 0.107  -13.169 4.464  1.187  -2.440 3.827  "HB'1" G2L 44 
G2L "HB'2" 2HB* H 0 0 N N N -0.983 -11.922 3.815  1.362  -0.735 4.342  "HB'2" G2L 45 
G2L "HD'1" 1HD* H 0 0 N N N -0.829 -14.753 2.912  3.405  -1.242 5.809  "HD'1" G2L 46 
G2L "HD'2" 2HD* H 0 0 N N N -0.746 -14.377 1.180  4.345  -2.626 5.172  "HD'2" G2L 47 
G2L "HD'3" 3HD* H 0 0 N N N -1.882 -13.492 2.217  2.598  -2.798 5.484  "HD'3" G2L 48 
# 
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 
G2L OP3   P      SING N N 1  
G2L OP3   HOP3   SING N N 2  
G2L P     OP1    DOUB N N 3  
G2L P     OP2    SING N N 4  
G2L P     "O5'"  SING N N 5  
G2L OP2   HOP2   SING N N 6  
G2L "O5'" "C5'"  SING N N 7  
G2L "C5'" "C4'"  SING N N 8  
G2L "C5'" "H5'"  SING N N 9  
G2L "C5'" "H5''" SING N N 10 
G2L "C4'" "O4'"  SING N N 11 
G2L "C4'" "C3'"  SING N N 12 
G2L "C4'" "H4'"  SING N N 13 
G2L "O4'" "C1'"  SING N N 14 
G2L "C3'" "O3'"  SING N N 15 
G2L "C3'" "C2'"  SING N N 16 
G2L "C3'" "H3'"  SING N N 17 
G2L "O3'" "CA'"  SING N N 18 
G2L "C2'" "O2'"  SING N N 19 
G2L "C2'" "C1'"  SING N N 20 
G2L "C2'" "H2'"  SING N N 21 
G2L "O2'" "HO2'" SING N N 22 
G2L "C1'" N9     SING N N 23 
G2L "C1'" "H1'"  SING N N 24 
G2L N9    C8     SING Y N 25 
G2L N9    C4     SING Y N 26 
G2L C8    N7     DOUB Y N 27 
G2L C8    H8     SING N N 28 
G2L N7    C5     SING Y N 29 
G2L C5    C6     SING N N 30 
G2L C5    C4     DOUB Y N 31 
G2L C6    O6     DOUB N N 32 
G2L C6    N1     SING N N 33 
G2L N1    C2     SING N N 34 
G2L N1    H1     SING N N 35 
G2L C2    N2     SING N N 36 
G2L C2    N3     DOUB N N 37 
G2L N2    H21    SING N N 38 
G2L N2    H22    SING N N 39 
G2L N3    C4     SING N N 40 
G2L "CA'" "CB'"  SING N N 41 
G2L "CA'" "HA'1" SING N N 42 
G2L "CA'" "HA'2" SING N N 43 
G2L "CB'" "OC'"  SING N N 44 
G2L "CB'" "HB'1" SING N N 45 
G2L "CB'" "HB'2" SING N N 46 
G2L "OC'" "CD'"  SING N N 47 
G2L "CD'" "HD'1" SING N N 48 
G2L "CD'" "HD'2" SING N N 49 
G2L "CD'" "HD'3" SING N N 50 
# 
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 
G2L SMILES           ACDLabs              10.04 "O=C1c2ncn(c2N=C(N)N1)C3OC(C(OCCOC)C3O)COP(=O)(O)O"                                                                                                                                                    
G2L InChI            InChI                1.02b "InChI=1/C13H20N5O9P/c1-24-2-3-25-9-6(4-26-28(21,22)23)27-12(8(9)19)18-5-15-7-10(18)16-13(14)17-11(7)20/h5-6,8-9,12,19H,2-4H2,1H3,(H2,21,22,23)(H3,14,16,17,20)/t6-,8-,9-,12-/m1/s1/f/h17,21-22H,14H2" 
G2L InChIKey         InChI                1.02b ICKYKWCJEMPHMX-RBIOJLKGDK                                                                                                                                                                              
G2L SMILES_CANONICAL CACTVS               3.341 "COCCO[C@H]1[C@@H](O)[C@@H](O[C@@H]1CO[P](O)(O)=O)n2cnc3C(=O)NC(=Nc23)N"                                                                                                                               
G2L SMILES           CACTVS               3.341 "COCCO[CH]1[CH](O)[CH](O[CH]1CO[P](O)(O)=O)n2cnc3C(=O)NC(=Nc23)N"                                                                                                                                      
G2L SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COCCO[C@@H]1[C@H](O[C@H]([C@@H]1O)n2cnc3c2N=C(NC3=O)N)COP(=O)(O)O"                                                                                                                                    
G2L SMILES           "OpenEye OEToolkits" 1.5.0 "COCCOC1C(OC(C1O)n2cnc3c2N=C(NC3=O)N)COP(=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 
G2L "SYSTEMATIC NAME" ACDLabs              10.04 
;3'-O-(2-methoxyethyl)guanosine 5'-(dihydrogen phosphate)
;
G2L "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-3-(2-methoxyethoxy)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
