data_GCQ
# 
_chem_comp.id                                    GCQ 
_chem_comp.name                                  "GEMCITABINE DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C9 H13 F2 N3 O10 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "((2R,3R,5R)-5-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-4,4-DIFLUORO-3-HYDROXYTETRAHYDROFURAN-2-YL)METHYL TRIHYDROGEN DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-11-22 
_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                         ? 
_chem_comp.formula_weight                        423.158 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GCQ 
_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        2EUD 
_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 
GCQ O3B    O3B  O 0 1 N N N 27.556 53.497 17.439 -5.866 2.345  -0.831 O3B    GCQ 1  
GCQ PB     PB   P 0 1 N N N 27.583 53.005 16.010 -5.131 1.131  -0.070 PB     GCQ 2  
GCQ O1B    O1B  O 0 1 N N N 28.940 52.871 15.396 -6.212 -0.005 0.295  O1B    GCQ 3  
GCQ O2B    O2B  O 0 1 N N N 26.730 53.765 15.013 -4.506 1.635  1.174  O2B    GCQ 4  
GCQ O3A    O3A  O 0 1 N N N 27.176 51.456 16.177 -3.997 0.506  -1.026 O3A    GCQ 5  
GCQ PA     PA   P 0 1 N N S 26.062 50.482 15.517 -3.053 -0.405 -0.093 PA     GCQ 6  
GCQ O1A    O1A  O 0 1 N N N 26.561 49.141 15.957 -3.761 -1.828 0.160  O1A    GCQ 7  
GCQ O2A    O2A  O 0 1 N N N 25.907 50.681 13.982 -2.835 0.275  1.203  O2A    GCQ 8  
GCQ "O5'"  O5*  O 0 1 N N N 24.769 50.856 16.376 -1.636 -0.633 -0.824 "O5'"  GCQ 9  
GCQ "C5'"  C5*  C 0 1 N N N 23.540 50.189 16.173 -0.806 -1.343 0.097  "C5'"  GCQ 10 
GCQ "C4'"  C4*  C 0 1 N N R 22.393 50.855 16.925 0.563  -1.594 -0.539 "C4'"  GCQ 11 
GCQ "C3'"  C3*  C 0 1 N N R 21.191 51.143 16.069 1.464  -2.403 0.420  "C3'"  GCQ 12 
GCQ "O3'"  O3*  O 0 1 N N N 20.149 50.235 16.467 1.449  -3.789 0.072  "O3'"  GCQ 13 
GCQ "C2'"  C2*  C 0 1 N N N 20.842 52.604 16.294 2.875  -1.805 0.205  "C2'"  GCQ 14 
GCQ F1     F1   F 0 1 N N N 19.506 52.698 16.786 3.754  -2.783 -0.273 F1     GCQ 15 
GCQ "O4'"  O4*  O 0 1 N N N 22.772 52.068 17.632 1.261  -0.345 -0.737 "O4'"  GCQ 16 
GCQ "C1'"  C1*  C 0 1 N N R 21.848 53.147 17.321 2.655  -0.704 -0.857 "C1'"  GCQ 17 
GCQ N1     N1   N 0 1 Y N N 22.510 54.423 16.806 3.506  0.454  -0.573 N1     GCQ 18 
GCQ C6     C6   C 0 1 Y N N 23.651 54.422 16.019 4.474  0.818  -1.460 C6     GCQ 19 
GCQ C5     C5   C 0 1 Y N N 24.237 55.616 15.553 5.251  1.894  -1.190 C5     GCQ 20 
GCQ C4     C4   C 0 1 Y N N 23.633 56.848 15.907 5.041  2.602  0.011  C4     GCQ 21 
GCQ N4     N4   N 0 1 N N N 24.187 58.015 15.464 5.819  3.696  0.314  N4     GCQ 22 
GCQ N3     N3   N 0 1 Y N N 22.500 56.865 16.690 4.087  2.211  0.845  N3     GCQ 23 
GCQ C2     C2   C 0 1 Y N N 21.916 55.703 17.152 3.327  1.154  0.563  C2     GCQ 24 
GCQ O2     O2   O 0 1 N N N 20.874 55.747 17.868 2.456  0.815  1.346  O2     GCQ 25 
GCQ F2     F2   F 0 1 N N N 20.837 53.254 15.141 3.358  -1.248 1.394  F2     GCQ 26 
GCQ H3B    H3B  H 0 1 N N N 27.550 52.753 18.030 -6.536 2.690  -0.225 H3B    GCQ 27 
GCQ H1B    H1B  H 0 1 N N N 28.859 52.843 14.450 -6.595 -0.306 -0.540 H1B    GCQ 28 
GCQ H1A    H1A  H 0 1 N N N 26.667 48.578 15.199 -3.885 -2.237 -0.708 H1A    GCQ 29 
GCQ "H5'1" 1H5* H 0 0 N N N 23.644 49.162 16.553 -1.272 -2.297 0.345  "H5'1" GCQ 30 
GCQ "H5'2" 2H5* H 0 0 N N N 23.308 50.201 15.098 -0.682 -0.753 1.005  "H5'2" GCQ 31 
GCQ "H4'"  H4*  H 0 1 N N N 22.117 50.094 17.670 0.450  -2.120 -1.487 "H4'"  GCQ 32 
GCQ "H3'"  H3*  H 0 1 N N N 21.359 50.992 14.992 1.143  -2.265 1.453  "H3'"  GCQ 33 
GCQ H1     H1   H 0 1 N N N 20.239 50.035 17.391 2.026  -4.241 0.702  H1     GCQ 34 
GCQ "H1'"  H1*  H 0 1 N N N 21.358 53.454 18.257 2.863  -1.092 -1.854 "H1'"  GCQ 35 
GCQ H6     H6   H 0 1 N N N 24.105 53.478 15.755 4.618  0.256  -2.371 H6     GCQ 36 
GCQ H5     H5   H 0 1 N N N 25.126 55.593 14.940 6.024  2.199  -1.879 H5     GCQ 37 
GCQ HN41   1HN4 H 0 0 N N N 25.005 58.091 14.894 5.670  4.184  1.139  HN41   GCQ 38 
GCQ HN42   2HN4 H 0 0 N N N 23.641 58.781 15.802 6.519  3.977  -0.296 HN42   GCQ 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 
GCQ O3B   PB     SING N N 1  
GCQ O3B   H3B    SING N N 2  
GCQ PB    O1B    SING N N 3  
GCQ PB    O2B    DOUB N N 4  
GCQ PB    O3A    SING N N 5  
GCQ O1B   H1B    SING N N 6  
GCQ O3A   PA     SING N N 7  
GCQ PA    O1A    SING N N 8  
GCQ PA    O2A    DOUB N N 9  
GCQ PA    "O5'"  SING N N 10 
GCQ O1A   H1A    SING N N 11 
GCQ "O5'" "C5'"  SING N N 12 
GCQ "C5'" "C4'"  SING N N 13 
GCQ "C5'" "H5'1" SING N N 14 
GCQ "C5'" "H5'2" SING N N 15 
GCQ "C4'" "C3'"  SING N N 16 
GCQ "C4'" "O4'"  SING N N 17 
GCQ "C4'" "H4'"  SING N N 18 
GCQ "C3'" "O3'"  SING N N 19 
GCQ "C3'" "C2'"  SING N N 20 
GCQ "C3'" "H3'"  SING N N 21 
GCQ "O3'" H1     SING N N 22 
GCQ "C2'" F1     SING N N 23 
GCQ "C2'" "C1'"  SING N N 24 
GCQ "C2'" F2     SING N N 25 
GCQ "O4'" "C1'"  SING N N 26 
GCQ "C1'" N1     SING N N 27 
GCQ "C1'" "H1'"  SING N N 28 
GCQ N1    C6     SING Y N 29 
GCQ N1    C2     SING Y N 30 
GCQ C6    C5     DOUB Y N 31 
GCQ C6    H6     SING N N 32 
GCQ C5    C4     SING Y N 33 
GCQ C5    H5     SING N N 34 
GCQ C4    N4     SING N N 35 
GCQ C4    N3     DOUB Y N 36 
GCQ N4    HN41   SING N N 37 
GCQ N4    HN42   SING N N 38 
GCQ N3    C2     SING Y N 39 
GCQ C2    O2     DOUB 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 
GCQ SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCC2OC(N1C(=O)N=C(N)C=C1)C(F)(F)C2O                                                                                                                                      
GCQ InChI            InChI                1.02b InChI=1/C9H13F2N3O10P2/c10-9(11)6(15)4(3-22-26(20,21)24-25(17,18)19)23-7(9)14-2-1-5(12)13-8(14)16/h1-2,4,6-7,15H,3H2,(H,20,21)(H2,12,13,16)(H2,17,18,19)/t4-,6-,7-/m1/s1/f/h17-18,20H,12H2 
GCQ InChIKey         InChI                1.02b FRQISCZGNNXEMD-CRCAOFBEDY                                                                                                                                                                  
GCQ SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO[P@@](O)(=O)O[P](O)(O)=O)[C@@H](O)C2(F)F                                                                                                                  
GCQ SMILES           CACTVS               3.341 NC1=NC(=O)N(C=C1)[CH]2O[CH](CO[P](O)(=O)O[P](O)(O)=O)[CH](O)C2(F)F                                                                                                                         
GCQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO[P@](=O)(O)OP(=O)(O)O)O)(F)F                                                                                                                    
GCQ SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)O)O)(F)F                                                                                                                                    
# 
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 
GCQ "SYSTEMATIC NAME" ACDLabs              10.04 
;2'-deoxy-2',2'-difluorocytidine 5'-(trihydrogen diphosphate)
;
GCQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-oxolan-2-yl]methyl phosphono hydrogen phosphate" 
# 
