data_GAO
# 
_chem_comp.id                                    GAO 
_chem_comp.name                                  
;GUANINE ARABINOSE-5'-PHOSPHATE
;
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H14 N5 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               G 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-12-18 
_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                        363.221 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     GAO 
_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        1HO6 
_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 
GAO OP3    O3P  O 0 1 N Y N -9.518  2.864 4.985 -1.962 -1.342 5.576  OP3    GAO 1  
GAO P      P    P 0 1 N N N -9.513  2.683 3.380 -0.885 -0.299 4.989  P      GAO 2  
GAO OP1    O1P  O 0 1 N N N -10.821 3.135 2.860 -1.524 1.023  4.815  OP1    GAO 3  
GAO OP2    O2P  O 0 1 N N N -9.025  1.320 3.062 0.348  -0.169 6.015  OP2    GAO 4  
GAO "O5'"  O5*  O 0 1 N N N -8.392  3.737 2.908 -0.347 -0.827 3.566  "O5'"  GAO 5  
GAO "C5'"  C5*  C 0 1 N N N -8.604  5.161 3.034 0.599  0.135  3.100  "C5'"  GAO 6  
GAO "C4'"  C4*  C 0 1 N N R -7.298  5.933 3.054 1.152  -0.308 1.744  "C4'"  GAO 7  
GAO "O4'"  O4*  O 0 1 N N N -6.437  5.460 4.095 0.089  -0.390 0.770  "O4'"  GAO 8  
GAO "C3'"  C3*  C 0 1 N N S -6.543  5.771 1.746 2.121  0.755  1.182  "C3'"  GAO 9  
GAO "O3'"  O3*  O 0 1 N N N -6.734  6.915 0.897 3.476  0.390  1.451  "O3'"  GAO 10 
GAO "C2'"  C2*  C 0 1 N N S -5.098  5.609 2.138 1.848  0.745  -0.340 "C2'"  GAO 11 
GAO "O2'"  O2*  O 0 1 N N N -4.569  4.376 1.623 1.383  2.025  -0.773 "O2'"  GAO 12 
GAO "C1'"  C1*  C 0 1 N N R -5.084  5.637 3.658 0.744  -0.320 -0.514 "C1'"  GAO 13 
GAO N9     N9   N 0 1 Y N N -4.211  4.592 4.209 -0.206 0.094  -1.549 N9     GAO 14 
GAO C8     C8   C 0 1 Y N N -4.309  3.251 4.105 -1.324 0.854  -1.361 C8     GAO 15 
GAO N7     N7   N 0 1 Y N N -3.416  2.535 4.701 -1.935 1.028  -2.496 N7     GAO 16 
GAO C5     C5   C 0 1 Y N N -2.609  3.523 5.280 -1.248 0.394  -3.477 C5     GAO 17 
GAO C6     C6   C 0 1 N N N -1.440  3.404 6.079 -1.434 0.244  -4.871 C6     GAO 18 
GAO O6     O6   O 0 1 N N N -0.852  2.390 6.443 -2.390 0.753  -5.432 O6     GAO 19 
GAO N1     N1   N 0 1 N N N -0.954  4.645 6.444 -0.524 -0.472 -5.567 N1     GAO 20 
GAO C2     C2   C 0 1 N N N -1.507  5.853 6.092 0.536  -1.041 -4.929 C2     GAO 21 
GAO N2     N2   N 0 1 N N N -0.892  6.933 6.532 1.441  -1.768 -5.660 N2     GAO 22 
GAO N3     N3   N 0 1 N N N -2.595  5.980 5.350 0.721  -0.909 -3.634 N3     GAO 23 
GAO C4     C4   C 0 1 Y N N -3.096  4.785 4.978 -0.135 -0.209 -2.881 C4     GAO 24 
GAO HOP3   3HOP H 0 0 N N N -8.677  2.573 5.319 -2.258 -0.990 6.426  HOP3   GAO 25 
GAO HOP2   2HOP H 0 0 N N N -9.022  1.213 2.118 0.735  -1.051 6.100  HOP2   GAO 26 
GAO "H5'"  1H5* H 0 1 N N N -9.285  5.540 2.236 1.417  0.217  3.817  "H5'"  GAO 27 
GAO "H5''" 2H5* H 0 0 N N N -9.227  5.399 3.927 0.111  1.104  2.994  "H5''" GAO 28 
GAO "H4'"  H4*  H 0 1 N N N -7.566  7.002 3.220 1.657  -1.269 1.837  "H4'"  GAO 29 
GAO "H3'"  H3*  H 0 1 N N N -6.906  4.894 1.160 1.900  1.735  1.605  "H3'"  GAO 30 
GAO "HO3'" H3T  H 0 0 N Y N -6.261  6.813 0.078 4.033  1.087  1.078  "HO3'" GAO 31 
GAO "H2'"  H2*  H 0 1 N N N -4.455  6.417 1.717 2.747  0.461  -0.887 "H2'"  GAO 32 
GAO "HO2'" 2HO* H 0 0 N N N -3.657  4.273 1.870 2.088  2.658  -0.582 "HO2'" GAO 33 
GAO "H1'"  H1*  H 0 1 N N N -4.675  6.608 4.021 1.184  -1.284 -0.769 "H1'"  GAO 34 
GAO H8     H8   H 0 1 N N N -5.109  2.745 3.539 -1.652 1.250  -0.411 H8     GAO 35 
GAO H1     H1   H 0 1 N N N -0.114  4.671 7.023 -0.631 -0.588 -6.524 H1     GAO 36 
GAO H21    1H2  H 0 1 N N N -1.302  7.829 6.270 2.204  -2.177 -5.221 H21    GAO 37 
GAO H22    2H2  H 0 1 N N N 0.087   6.908 6.249 1.316  -1.878 -6.616 H22    GAO 38 
# 
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 
GAO OP3   P      SING N N 1  
GAO OP3   HOP3   SING N N 2  
GAO P     OP1    DOUB N N 3  
GAO P     OP2    SING N N 4  
GAO P     "O5'"  SING N N 5  
GAO OP2   HOP2   SING N N 6  
GAO "O5'" "C5'"  SING N N 7  
GAO "C5'" "C4'"  SING N N 8  
GAO "C5'" "H5'"  SING N N 9  
GAO "C5'" "H5''" SING N N 10 
GAO "C4'" "O4'"  SING N N 11 
GAO "C4'" "C3'"  SING N N 12 
GAO "C4'" "H4'"  SING N N 13 
GAO "O4'" "C1'"  SING N N 14 
GAO "C3'" "O3'"  SING N N 15 
GAO "C3'" "C2'"  SING N N 16 
GAO "C3'" "H3'"  SING N N 17 
GAO "O3'" "HO3'" SING N N 18 
GAO "C2'" "O2'"  SING N N 19 
GAO "C2'" "C1'"  SING N N 20 
GAO "C2'" "H2'"  SING N N 21 
GAO "O2'" "HO2'" SING N N 22 
GAO "C1'" N9     SING N N 23 
GAO "C1'" "H1'"  SING N N 24 
GAO N9    C8     SING Y N 25 
GAO N9    C4     SING Y N 26 
GAO C8    N7     DOUB Y N 27 
GAO C8    H8     SING N N 28 
GAO N7    C5     SING Y N 29 
GAO C5    C6     SING N N 30 
GAO C5    C4     DOUB Y N 31 
GAO C6    O6     DOUB N N 32 
GAO C6    N1     SING N N 33 
GAO N1    C2     SING N N 34 
GAO N1    H1     SING N N 35 
GAO C2    N2     SING N N 36 
GAO C2    N3     DOUB N N 37 
GAO N2    H21    SING N N 38 
GAO N2    H22    SING N N 39 
GAO N3    C4     SING N N 40 
# 
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 
GAO SMILES           ACDLabs              10.04 "O=C1c2ncn(c2N=C(N)N1)C3OC(C(O)C3O)COP(=O)(O)O"                                                                                                                                       
GAO InChI            InChI                1.02b "InChI=1/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6+,9-/m1/s1/f/h14,19-20H,11H2" 
GAO InChIKey         InChI                1.02b RQFCJASXJCIDSX-LYAMUNPVDV                                                                                                                                                             
GAO SMILES_CANONICAL CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@@H]3O"                                                                                                                  
GAO SMILES           CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O"                                                                                                                         
GAO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N=C(NC2=O)N"                                                                                                                    
GAO SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C(C(C(O3)COP(=O)(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 
GAO "SYSTEMATIC NAME" ACDLabs              10.04 "2-amino-9-(5-O-phosphono-beta-D-arabinofuranosyl)-1,9-dihydro-6H-purin-6-one"                         
GAO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
