data_GCP
# 
_chem_comp.id                                    GCP 
_chem_comp.name                                  "PHOSPHOMETHYLPHOSPHONIC ACID GUANYLATE ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H18 N5 O13 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         GTO 
_chem_comp.formula_weight                        521.208 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GCP 
_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        1HOP 
_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 
GCP PG     PG   P 0 1 N N N 8.611 24.356 -18.319 -1.285 -0.306 7.434  PG     GCP 1  
GCP O1G    O1G  O 0 1 N N N 9.946 24.604 -17.696 -1.812 1.072  7.323  O1G    GCP 2  
GCP O2G    O2G  O 0 1 N N N 8.464 22.985 -18.867 -2.228 -1.163 8.418  O2G    GCP 3  
GCP O3G    O3G  O 0 1 N N N 8.152 25.445 -19.223 0.210  -0.261 8.029  O3G    GCP 4  
GCP C3B    C3B  C 0 1 N N N 7.382 24.457 -17.000 -1.260 -1.083 5.786  C3B    GCP 5  
GCP PB     PB   P 0 1 N N R 6.838 23.478 -15.600 -0.192 -0.111 4.672  PB     GCP 6  
GCP O1B    O1B  O 0 1 N N N 8.013 22.870 -14.923 -0.719 1.266  4.560  O1B    GCP 7  
GCP O2B    O2B  O 0 1 N N N 6.078 24.506 -14.877 1.303  -0.067 5.267  O2B    GCP 8  
GCP O3A    O3A  O 0 1 N N N 5.744 22.325 -15.930 -0.170 -0.798 3.216  O3A    GCP 9  
GCP PA     PA   P 0 1 N N S 4.424 21.795 -15.117 0.786  0.106  2.290  PA     GCP 10 
GCP O1A    O1A  O 0 1 N N N 4.095 22.670 -13.959 0.244  1.481  2.215  O1A    GCP 11 
GCP O2A    O2A  O 0 1 N N N 3.404 21.555 -16.176 2.265  0.147  2.925  O2A    GCP 12 
GCP "O5'"  O5*  O 0 1 N N N 4.586 20.385 -14.335 0.855  -0.525 0.810  "O5'"  GCP 13 
GCP "C5'"  C5*  C 0 1 N N N 5.327 19.200 -14.753 1.714  0.318  0.041  "C5'"  GCP 14 
GCP "C4'"  C4*  C 0 1 N N R 4.674 17.905 -14.320 1.823  -0.229 -1.383 "C4'"  GCP 15 
GCP "O4'"  O4*  O 0 1 N N N 4.837 17.700 -12.940 0.526  -0.237 -2.019 "O4'"  GCP 16 
GCP "C3'"  C3*  C 0 1 N N S 3.189 18.015 -14.467 2.685  0.708  -2.258 "C3'"  GCP 17 
GCP "O3'"  O3*  O 0 1 N N N 2.827 17.409 -15.728 4.023  0.216  -2.350 "O3'"  GCP 18 
GCP "C2'"  C2*  C 0 1 N N R 2.686 17.409 -13.181 1.995  0.670  -3.642 "C2'"  GCP 19 
GCP "O2'"  O2*  O 0 1 N N N 1.740 16.472 -13.696 2.888  0.156  -4.632 "O2'"  GCP 20 
GCP "C1'"  C1*  C 0 1 N N R 3.903 16.763 -12.448 0.797  -0.282 -3.437 "C1'"  GCP 21 
GCP N9     N9   N 0 1 Y N N 4.139 16.877 -11.086 -0.364 0.189  -4.194 N9     GCP 22 
GCP C8     C8   C 0 1 Y N N 4.410 18.049 -10.451 -1.313 1.065  -3.753 C8     GCP 23 
GCP N7     N7   N 0 1 Y N N 4.900 18.009 -9.232  -2.200 1.260  -4.685 N7     GCP 24 
GCP C5     C5   C 0 1 Y N N 4.971 16.623 -9.015  -1.875 0.523  -5.775 C5     GCP 25 
GCP C6     C6   C 0 1 Y N N 5.424 15.933 -7.861  -2.458 0.342  -7.051 C6     GCP 26 
GCP O6     O6   O 0 1 N N N 5.895 16.426 -6.838  -3.483 0.926  -7.358 O6     GCP 27 
GCP N1     N1   N 0 1 Y N N 5.338 14.550 -7.983  -1.846 -0.488 -7.923 N1     GCP 28 
GCP C2     C2   C 0 1 Y N N 4.898 13.847 -9.094  -0.703 -1.140 -7.568 C2     GCP 29 
GCP N2     N2   N 0 1 N N N 4.889 12.511 -9.019  -0.107 -1.982 -8.472 N2     GCP 30 
GCP N3     N3   N 0 1 Y N N 4.477 14.525 -10.199 -0.152 -0.980 -6.385 N3     GCP 31 
GCP C4     C4   C 0 1 Y N N 4.518 15.910 -10.118 -0.697 -0.169 -5.472 C4     GCP 32 
GCP HOG2   2HOG H 0 0 N N N 7.615 22.827 -19.263 -2.214 -0.719 9.277  HOG2   GCP 33 
GCP HOG3   3HOG H 0 0 N N N 7.303 25.287 -19.619 0.515  -1.177 8.086  HOG3   GCP 34 
GCP H3B1   1H3B H 0 0 N N N 7.616 25.439 -16.528 -2.272 -1.113 5.383  H3B1   GCP 35 
GCP H3B2   2H3B H 0 0 N N N 6.434 24.611 -17.566 -0.871 -2.098 5.868  H3B2   GCP 36 
GCP HOB2   2HOB H 0 0 N N N 5.789 23.987 -14.135 1.609  -0.983 5.324  HOB2   GCP 37 
GCP HOA2   2HOA H 0 0 N N N 2.638 21.247 -15.704 2.581  -0.765 2.956  HOA2   GCP 38 
GCP "H5'2" 2H5* H 0 0 N N N 5.345 19.191 -15.840 1.302  1.327  0.012  "H5'2" GCP 39 
GCP "H5'1" 1H5* H 0 0 N N N 6.338 19.251 -14.345 2.703  0.342  0.497  "H5'1" GCP 40 
GCP "H4'"  H4*  H 0 1 N N N 5.071 17.062 -14.887 2.246  -1.233 -1.372 "H4'"  GCP 41 
GCP "H3'"  H3*  H 0 1 N N N 2.870 19.059 -14.440 2.678  1.720  -1.854 "H3'"  GCP 42 
GCP "HO3'" *HO3 H 0 0 N N N 3.454 16.705 -15.927 4.512  0.838  -2.905 "HO3'" GCP 43 
GCP "H2'"  H2*  H 0 1 N N N 2.231 18.193 -12.573 1.647  1.664  -3.922 "H2'"  GCP 44 
GCP "HO2'" *HO2 H 0 0 N N N 0.940 16.955 -13.924 3.642  0.761  -4.670 "HO2'" GCP 45 
GCP "H1'"  H1*  H 0 1 N N N 4.110 15.755 -12.813 1.062  -1.295 -3.741 "H1'"  GCP 46 
GCP H8     H8   H 0 1 N N N 4.242 19.009 -10.940 -1.325 1.528  -2.777 H8     GCP 47 
GCP HN1    HN1  H 0 1 N N N 5.616 13.961 -7.209  -2.227 -0.628 -8.804 HN1    GCP 48 
GCP HN21   1HN2 H 0 0 N N N 5.407 11.980 -9.664  0.708  -2.450 -8.235 HN21   GCP 49 
GCP HN22   2HN2 H 0 0 N N N 4.318 12.041 -8.375  -0.505 -2.113 -9.348 HN22   GCP 50 
# 
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 
GCP PG    O1G    DOUB N N 1  
GCP PG    O2G    SING N N 2  
GCP PG    O3G    SING N N 3  
GCP PG    C3B    SING N N 4  
GCP O2G   HOG2   SING N N 5  
GCP O3G   HOG3   SING N N 6  
GCP C3B   PB     SING N N 7  
GCP C3B   H3B1   SING N N 8  
GCP C3B   H3B2   SING N N 9  
GCP PB    O1B    DOUB N N 10 
GCP PB    O2B    SING N N 11 
GCP PB    O3A    SING N N 12 
GCP O2B   HOB2   SING N N 13 
GCP O3A   PA     SING N N 14 
GCP PA    O1A    DOUB N N 15 
GCP PA    O2A    SING N N 16 
GCP PA    "O5'"  SING N N 17 
GCP O2A   HOA2   SING N N 18 
GCP "O5'" "C5'"  SING N N 19 
GCP "C5'" "C4'"  SING N N 20 
GCP "C5'" "H5'2" SING N N 21 
GCP "C5'" "H5'1" SING N N 22 
GCP "C4'" "O4'"  SING N N 23 
GCP "C4'" "C3'"  SING N N 24 
GCP "C4'" "H4'"  SING N N 25 
GCP "O4'" "C1'"  SING N N 26 
GCP "C3'" "O3'"  SING N N 27 
GCP "C3'" "C2'"  SING N N 28 
GCP "C3'" "H3'"  SING N N 29 
GCP "O3'" "HO3'" SING N N 30 
GCP "C2'" "O2'"  SING N N 31 
GCP "C2'" "C1'"  SING N N 32 
GCP "C2'" "H2'"  SING N N 33 
GCP "O2'" "HO2'" SING N N 34 
GCP "C1'" N9     SING N N 35 
GCP "C1'" "H1'"  SING N N 36 
GCP N9    C8     SING Y N 37 
GCP N9    C4     SING Y N 38 
GCP C8    N7     DOUB Y N 39 
GCP C8    H8     SING N N 40 
GCP N7    C5     SING Y N 41 
GCP C5    C6     SING Y N 42 
GCP C5    C4     DOUB Y N 43 
GCP C6    O6     DOUB N N 44 
GCP C6    N1     SING Y N 45 
GCP N1    C2     SING Y N 46 
GCP N1    HN1    SING N N 47 
GCP C2    N2     SING N N 48 
GCP C2    N3     DOUB Y N 49 
GCP N2    HN21   SING N N 50 
GCP N2    HN22   SING N N 51 
GCP N3    C4     SING Y N 52 
# 
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 
GCP SMILES           ACDLabs              10.04 O=P(O)(O)CP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)C(O)C3O 
GCP InChI            InChI                1.02b 
InChI=1/C11H18N5O13P3/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(28-10)1-27-32(25,26)29-31(23,24)3-30(20,21)22/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1/f/h15,20-21,23,25H,12H2 
GCP InChIKey         InChI                1.02b PHBDHXOBFUBCJD-KWPOQKRIDJ 
GCP SMILES_CANONICAL CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)C[P](O)(O)=O)[C@@H](O)[C@H]3O 
GCP SMILES           CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)C[P](O)(O)=O)[CH](O)[CH]3O 
GCP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(CP(=O)(O)O)O)O)O)N=C(NC2=O)N 
GCP SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OP(=O)(CP(=O)(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 
GCP "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-hydroxy{[(R)-hydroxy(phosphonomethyl)phosphoryl]oxy}phosphoryl]guanosine"                                                                 
GCP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]methylphosphonic acid" 
# 
