data_GEO
# 
_chem_comp.id                                    GEO 
_chem_comp.name                                  GEMCITABINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C9 H11 F2 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2',2'-DIFLUORODEOXYCYTIDINE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-04-29 
_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                        263.198 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GEO 
_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        1P62 
_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 
GEO "O5'"  "O5'"  O 0 1 N N N 69.971 38.095 20.611 -3.334 2.813  -0.531 "O5'"  GEO 1  
GEO "C5'"  "C5'"  C 0 1 N N N 70.268 37.346 21.792 -3.226 1.662  0.310  "C5'"  GEO 2  
GEO "C4'"  "C4'"  C 0 1 N N R 70.467 35.860 21.371 -2.441 0.570  -0.419 "C4'"  GEO 3  
GEO "O4'"  "O4'"  O 0 1 N N N 69.149 35.328 21.046 -1.070 0.980  -0.614 "O4'"  GEO 4  
GEO "C1'"  "C1'"  C 0 1 N N R 69.210 34.473 19.901 -0.334 -0.243 -0.834 "C1'"  GEO 5  
GEO N1     N1     N 0 1 Y N N 67.922 34.422 19.161 1.090  -0.036 -0.561 N1     GEO 6  
GEO C6     C6     C 0 1 Y N N 67.146 35.472 18.997 2.017  -0.395 -1.493 C6     GEO 7  
GEO C5     C5     C 0 1 Y N N 65.911 35.351 18.582 3.331  -0.194 -1.232 C5     GEO 8  
GEO C4     C4     C 0 1 Y N N 65.456 34.201 18.160 3.703  0.371  0.005  C4     GEO 9  
GEO N3     N3     N 0 1 Y N N 66.250 33.126 18.194 2.765  0.704  0.882  N3     GEO 10 
GEO C2     C2     C 0 1 Y N N 67.498 33.222 18.696 1.476  0.506  0.608  C2     GEO 11 
GEO O2     O2     O 0 1 N N N 68.273 32.128 18.727 0.633  0.821  1.431  O2     GEO 12 
GEO N4     N4     N 0 1 N N N 64.225 34.032 17.639 5.030  0.582  0.298  N4     GEO 13 
GEO "C2'"  "C2'"  C 0 1 N N N 70.386 35.084 19.098 -0.933 -1.252 0.171  "C2'"  GEO 14 
GEO F1     F1     F 0 1 N N N 69.943 36.062 18.337 -0.176 -1.279 1.347  F1     GEO 15 
GEO F2     F2     F 0 1 N N N 70.869 34.206 18.263 -1.005 -2.529 -0.396 F2     GEO 16 
GEO "C3'"  "C3'"  C 0 1 N N R 71.368 35.602 20.169 -2.352 -0.703 0.451  "C3'"  GEO 17 
GEO "O3'"  "O3'"  O 0 1 N N N 72.407 34.586 20.411 -3.344 -1.652 0.055  "O3'"  GEO 18 
GEO "H5'"  "H5'"  H 0 1 N N N 69.849 39.001 20.867 -3.834 3.475  -0.035 "H5'"  GEO 19 
GEO "H5'1" "1H5'" H 0 0 N N N 71.136 37.756 22.358 -4.223 1.294  0.551  "H5'1" GEO 20 
GEO "H5'2" "2H5'" H 0 0 N N N 69.499 37.471 22.589 -2.706 1.931  1.229  "H5'2" GEO 21 
GEO "H4'"  "H4'"  H 0 1 N N N 70.979 35.371 22.232 -2.909 0.342  -1.377 "H4'"  GEO 22 
GEO "H1'"  "H1'"  H 0 1 N N N 69.378 33.397 20.143 -0.478 -0.594 -1.856 "H1'"  GEO 23 
GEO H6     H6     H 0 1 N N N 67.540 36.479 19.212 1.708  -0.831 -2.432 H6     GEO 24 
GEO H5     H5     H 0 1 N N N 65.244 36.230 18.588 4.082  -0.471 -1.957 H5     GEO 25 
GEO HN41   1HN4   H 0 0 N N N 63.869 33.134 17.309 5.282  0.975  1.148  HN41   GEO 26 
GEO HN42   2HN4   H 0 0 N N N 64.129 34.694 16.869 5.714  0.334  -0.344 HN42   GEO 27 
GEO "H3'"  "H3'"  H 0 1 N N N 71.930 36.523 19.890 -2.464 -0.453 1.506  "H3'"  GEO 28 
GEO H1     H1     H 0 1 N N N 72.968 34.425 19.661 -3.240 -2.422 0.630  H1     GEO 29 
# 
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 
GEO "O5'" "C5'"  SING N N 1  
GEO "O5'" "H5'"  SING N N 2  
GEO "C5'" "C4'"  SING N N 3  
GEO "C5'" "H5'1" SING N N 4  
GEO "C5'" "H5'2" SING N N 5  
GEO "C4'" "O4'"  SING N N 6  
GEO "C4'" "C3'"  SING N N 7  
GEO "C4'" "H4'"  SING N N 8  
GEO "O4'" "C1'"  SING N N 9  
GEO "C1'" N1     SING N N 10 
GEO "C1'" "C2'"  SING N N 11 
GEO "C1'" "H1'"  SING N N 12 
GEO N1    C6     SING Y N 13 
GEO N1    C2     SING Y N 14 
GEO C6    C5     DOUB Y N 15 
GEO C6    H6     SING N N 16 
GEO C5    C4     SING Y N 17 
GEO C5    H5     SING N N 18 
GEO C4    N3     DOUB Y N 19 
GEO C4    N4     SING N N 20 
GEO N3    C2     SING Y N 21 
GEO C2    O2     DOUB N N 22 
GEO N4    HN41   SING N N 23 
GEO N4    HN42   SING N N 24 
GEO "C2'" F1     SING N N 25 
GEO "C2'" F2     SING N N 26 
GEO "C2'" "C3'"  SING N N 27 
GEO "C3'" "O3'"  SING N N 28 
GEO "C3'" "H3'"  SING N N 29 
GEO "O3'" H1     SING N N 30 
# 
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 
GEO SMILES           ACDLabs              10.04 O=C1N=C(N)C=CN1C2OC(C(O)C2(F)F)CO                                                                                                  
GEO InChI            InChI                1.02b InChI=1/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1/f/h12H2 
GEO InChIKey         InChI                1.02b SDUQYLNIPVEERB-NXUZUIIMDQ                                                                                                          
GEO SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F                                                                                  
GEO SMILES           CACTVS               3.341 NC1=NC(=O)N(C=C1)[CH]2O[CH](CO)[CH](O)C2(F)F                                                                                       
GEO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F                                                                                 
GEO SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)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 
GEO "SYSTEMATIC NAME" ACDLabs              10.04 "2'-deoxy-2',2'-difluorocytidine"                                                         
GEO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one 
# 
