data_8MG
# 
_chem_comp.id                                    8MG 
_chem_comp.name                                  "8-METHYL-2'-DEOXYGUANOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H16 N5 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               DG 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-10-08 
_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                        361.248 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     8MG 
_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        1R4D 
_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 
8MG P      P    P 0 1 N N N 57.403 40.169 -22.009 1.592  -1.245 -4.964 P      8MG 1  
8MG OP3    O3P  O 0 1 N Y N 56.374 39.226 -22.521 0.339  -0.227 -4.868 OP3    8MG 2  
8MG OP2    O2P  O 0 1 N N N 57.058 41.098 -20.903 0.886  -2.697 -5.051 OP2    8MG 3  
8MG "O5'"  O5*  O 0 1 N N N 57.938 41.035 -23.236 2.211  -1.232 -3.468 "O5'"  8MG 4  
8MG N9     N9   N 0 1 Y N N 62.115 41.092 -24.302 1.818  1.923  -0.049 N9     8MG 5  
8MG C4     C4   C 0 1 Y N N 62.425 39.848 -23.806 1.989  2.586  -1.232 C4     8MG 6  
8MG N3     N3   N 0 1 N N N 61.871 38.678 -24.191 2.455  2.050  -2.381 N3     8MG 7  
8MG C2     C2   C 0 1 N N N 62.380 37.651 -23.532 2.516  2.919  -3.367 C2     8MG 8  
8MG N2     N2   N 0 1 N N N 61.938 36.416 -23.790 2.962  2.572  -4.616 N2     8MG 9  
8MG N1     N1   N 0 1 N N N 63.355 37.760 -22.574 2.128  4.272  -3.217 N1     8MG 10 
8MG C6     C6   C 0 1 N N N 63.939 38.953 -22.161 1.642  4.847  -2.035 C6     8MG 11 
8MG O6     O6   O 0 1 N N N 64.812 38.939 -21.285 1.305  6.017  -1.902 O6     8MG 12 
8MG C5     C5   C 0 1 Y N N 63.402 40.066 -22.859 1.587  3.875  -0.978 C5     8MG 13 
8MG N7     N7   N 0 1 Y N N 63.698 41.418 -22.759 1.175  4.040  0.311  N7     8MG 14 
8MG C8     C8   C 0 1 Y N N 62.910 41.987 -23.631 1.326  2.845  0.847  C8     8MG 15 
8MG "C2'"  C2*  C 0 1 N N N 60.935 40.312 -26.381 0.878  -0.312 0.578  "C2'"  8MG 16 
8MG "C5'"  C5*  C 0 1 N N N 57.672 40.647 -24.586 1.348  -1.500 -2.377 "C5'"  8MG 17 
8MG "C4'"  C4*  C 0 1 N N R 58.836 41.012 -25.478 2.156  -1.432 -1.088 "C4'"  8MG 18 
8MG "O4'"  O4*  O 0 1 N N N 59.885 41.622 -24.698 2.678  -0.093 -0.958 "O4'"  8MG 19 
8MG "C1'"  C1*  C 0 1 N N R 61.134 41.408 -25.338 2.101  0.516  0.211  "C1'"  8MG 20 
8MG "C3'"  C3*  C 0 1 N N S 59.507 39.833 -26.173 1.309  -1.697 0.152  "C3'"  8MG 21 
8MG "O3'"  O3*  O 0 1 N N N 58.871 39.575 -27.427 2.127  -2.250 1.180  "O3'"  8MG 22 
8MG C      C    C 0 1 N N N 62.703 43.309 -23.621 1.018  2.481  2.247  C      8MG 23 
8MG OP1    O1P  O 0 1 N N N ?      ?      ?       2.575  -0.951 -6.059 OP1    8MG 24 
8MG H3P    H3P  H 0 1 N N N 56.594 38.631 -23.228 -0.163 -0.014 -5.684 H3P    8MG 25 
8MG H2P    H2P  H 0 1 N N N 57.715 41.700 -20.575 0.508  -2.990 -5.907 H2P    8MG 26 
8MG H21    1H2  H 0 1 N N N 61.219 36.279 -24.486 3.584  3.192  -5.082 H21    8MG 27 
8MG H22    2H2  H 0 1 N N N 62.316 35.626 -23.284 2.647  1.715  -5.007 H22    8MG 28 
8MG H1     H1   H 0 1 N N N 63.680 36.914 -22.131 2.207  4.874  -4.031 H1     8MG 29 
8MG "H2'"  1H2* H 0 1 N N N 61.644 39.497 -26.262 0.008  0.008  -0.009 "H2'"  8MG 30 
8MG "H2''" 2H2* H 0 0 N N N 61.072 40.726 -27.380 0.635  -0.225 1.641  "H2''" 8MG 31 
8MG "H5'"  1H5* H 0 1 N N N 56.777 41.157 -24.942 0.551  -0.756 -2.359 "H5'"  8MG 32 
8MG "H5''" 2H5* H 0 0 N N N 57.512 39.570 -24.633 0.917  -2.495 -2.497 "H5''" 8MG 33 
8MG "H4'"  H4*  H 0 1 N N N 58.455 41.664 -26.267 3.008  -2.117 -1.157 "H4'"  8MG 34 
8MG "H1'"  H1*  H 0 1 N N N 61.430 42.341 -25.815 2.853  0.503  1.007  "H1'"  8MG 35 
8MG "H3'"  H3*  H 0 1 N N N 59.468 38.937 -25.557 0.475  -2.383 -0.018 "H3'"  8MG 36 
8MG "HO3'" H3T  H 0 0 N Y N 57.978 39.275 -27.297 2.928  -1.706 1.218  "HO3'" 8MG 37 
8MG HC1    1HC  H 0 1 N N N 62.967 43.725 -24.594 1.320  3.283  2.939  HC1    8MG 38 
8MG HC2    2HC  H 0 1 N N N 63.319 43.768 -22.849 -0.058 2.293  2.396  HC2    8MG 39 
8MG HC3    3HC  H 0 1 N N N 61.651 43.510 -23.414 1.536  1.557  2.555  HC3    8MG 40 
# 
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 
8MG P     OP3    SING N N 1  
8MG P     OP2    SING N N 2  
8MG P     "O5'"  SING N N 3  
8MG P     OP1    DOUB N N 4  
8MG OP3   H3P    SING N N 5  
8MG OP2   H2P    SING N N 6  
8MG "O5'" "C5'"  SING N N 7  
8MG N9    C4     SING Y N 8  
8MG N9    C8     SING Y N 9  
8MG N9    "C1'"  SING N N 10 
8MG C4    N3     SING N N 11 
8MG C4    C5     DOUB Y N 12 
8MG N3    C2     DOUB N N 13 
8MG C2    N2     SING N N 14 
8MG C2    N1     SING N N 15 
8MG N2    H21    SING N N 16 
8MG N2    H22    SING N N 17 
8MG N1    C6     SING N N 18 
8MG N1    H1     SING N N 19 
8MG C6    O6     DOUB N N 20 
8MG C6    C5     SING N N 21 
8MG C5    N7     SING Y N 22 
8MG N7    C8     DOUB Y N 23 
8MG C8    C      SING N N 24 
8MG "C2'" "C1'"  SING N N 25 
8MG "C2'" "C3'"  SING N N 26 
8MG "C2'" "H2'"  SING N N 27 
8MG "C2'" "H2''" SING N N 28 
8MG "C5'" "C4'"  SING N N 29 
8MG "C5'" "H5'"  SING N N 30 
8MG "C5'" "H5''" SING N N 31 
8MG "C4'" "O4'"  SING N N 32 
8MG "C4'" "C3'"  SING N N 33 
8MG "C4'" "H4'"  SING N N 34 
8MG "O4'" "C1'"  SING N N 35 
8MG "C1'" "H1'"  SING N N 36 
8MG "C3'" "O3'"  SING N N 37 
8MG "C3'" "H3'"  SING N N 38 
8MG "O3'" "HO3'" SING N N 39 
8MG C     HC1    SING N N 40 
8MG C     HC2    SING N N 41 
8MG C     HC3    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 
8MG SMILES           ACDLabs              10.04 "O=C1c2nc(n(c2N=C(N)N1)C3OC(C(O)C3)COP(=O)(O)O)C"                                                                                                                              
8MG InChI            InChI                1.02b "InChI=1/C11H16N5O7P/c1-4-13-8-9(14-11(12)15-10(8)18)16(4)7-2-5(17)6(23-7)3-22-24(19,20)21/h5-7,17H,2-3H2,1H3,(H2,19,20,21)(H3,12,14,15,18)/t5-,6+,7+/m0/s1/f/h15,19-20H,12H2" 
8MG InChIKey         InChI                1.02b MKPWVGWAKMPLFJ-PTCOHVBVDG                                                                                                                                                      
8MG SMILES_CANONICAL CACTVS               3.341 "Cc1nc2C(=O)NC(=Nc2n1[C@H]3C[C@H](O)[C@@H](CO[P](O)(O)=O)O3)N"                                                                                                                 
8MG SMILES           CACTVS               3.341 "Cc1nc2C(=O)NC(=Nc2n1[CH]3C[CH](O)[CH](CO[P](O)(O)=O)O3)N"                                                                                                                     
8MG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1nc2c(n1[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O)N=C(NC2=O)N"                                                                                                                   
8MG SMILES           "OpenEye OEToolkits" 1.5.0 "Cc1nc2c(n1C3CC(C(O3)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 
8MG "SYSTEMATIC NAME" ACDLabs              10.04 
;2'-deoxy-8-methylguanosine 5'-(dihydrogen phosphate)
;
8MG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(2-amino-8-methyl-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
