data_5FU
# 
_chem_comp.id                                    5FU 
_chem_comp.name                                  "5-FLUORO-URIDINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C9 H12 F N2 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               U 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-02 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        342.172 
_chem_comp.one_letter_code                       U 
_chem_comp.three_letter_code                     5FU 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
5FU F5     F5   F 0 1 N N N 30.317 50.796 122.253 -0.649 3.669  -3.091 F5     5FU 1  
5FU C5     C5   C 0 1 N N N 30.117 51.730 123.193 -0.519 3.544  -1.757 C5     5FU 2  
5FU C4     C4   C 0 1 N N N 31.066 52.184 124.081 -1.345 4.436  -0.930 C4     5FU 3  
5FU O4     O4   O 0 1 N N N 32.228 51.733 124.047 -2.111 5.251  -1.432 O4     5FU 4  
5FU N3     N3   N 0 1 N N N 30.693 53.138 125.003 -1.164 4.256  0.435  N3     5FU 5  
5FU C2     C2   C 0 1 N N N 29.421 53.679 125.081 -0.302 3.339  1.057  C2     5FU 6  
5FU O2     O2   O 0 1 N N N 29.138 54.558 125.930 -0.227 3.270  2.286  O2     5FU 7  
5FU C6     C6   C 0 1 N N N 29.076 52.370 123.485 0.309  2.664  -1.199 C6     5FU 8  
5FU N1     N1   N 0 1 N N N 28.493 53.240 124.207 0.452  2.524  0.177  N1     5FU 9  
5FU "C1'"  C1*  C 0 1 N N R 27.117 53.697 124.171 1.373  1.543  0.675  "C1'"  5FU 10 
5FU "O4'"  O4*  O 0 1 N N N 26.274 52.645 123.696 2.470  1.422  -0.246 "O4'"  5FU 11 
5FU "C2'"  C2*  C 0 1 N N R 27.001 54.864 123.214 0.748  0.163  0.786  "C2'"  5FU 12 
5FU "O2'"  O2*  O 0 1 N N N 26.303 55.919 123.878 0.137  -0.058 2.041  "O2'"  5FU 13 
5FU "C3'"  C3*  C 0 1 N N S 26.170 54.316 122.069 1.940  -0.742 0.560  "C3'"  5FU 14 
5FU "O3'"  O3*  O 0 1 N N N 25.265 55.298 121.600 2.742  -0.809 1.739  "O3'"  5FU 15 
5FU "C4'"  C4*  C 0 1 N N R 25.399 53.161 122.681 2.725  0.023  -0.498 "C4'"  5FU 16 
5FU "C5'"  C5*  C 0 1 N N N 25.057 52.098 121.663 2.282  -0.292 -1.921 "C5'"  5FU 17 
5FU "O5'"  O5*  O 0 1 N N N 26.286 51.550 121.203 3.063  0.476  -2.819 "O5'"  5FU 18 
5FU P      P    P 0 1 N N N 26.329 50.387 120.092 2.787  0.324  -4.407 P      5FU 19 
5FU O1P    O1P  O 0 1 N N N 27.683 50.405 119.426 3.659  1.172  -5.286 O1P    5FU 20 
5FU O2P    O2P  O 0 1 N N N 25.069 50.451 119.270 1.198  0.588  -4.548 O2P    5FU 21 
5FU O3P    O3P  O 0 1 N Y N ?      ?      ?       2.921  -1.270 -4.647 O3P    5FU 22 
5FU "HO'2" 2HO* H 0 0 N N N 26.148 55.676 124.783 -0.494 0.669  2.185  "HO'2" 5FU 23 
5FU "H2'"  H2*  H 0 1 N N N 27.967 55.260 122.869 -0.000 0.004  -0.000 "H2'"  5FU 24 
5FU "H1'"  H1*  H 0 1 N N N 26.813 53.999 125.184 1.754  1.910  1.633  "H1'"  5FU 25 
5FU "H4'"  H4*  H 0 1 N N N 24.429 53.489 123.084 3.804  -0.139 -0.410 "H4'"  5FU 26 
5FU "H5'1" 1H5* H 0 0 N N N 24.439 51.314 122.124 1.229  -0.035 -2.051 "H5'1" 5FU 27 
5FU "H5'2" 2H5* H 0 0 N N N 24.483 52.527 120.828 2.428  -1.352 -2.133 "H5'2" 5FU 28 
5FU HOP2   2HOP H 0 0 N N N 24.314 50.464 119.847 0.799  0.616  -5.443 HOP2   5FU 29 
5FU HOP3   3HOP H 0 0 N N N ?      ?      ?       2.886  -1.617 -5.563 HOP3   5FU 30 
5FU "H3'"  H3*  H 0 1 N N N 26.791 54.012 121.213 1.675  -1.764 0.277  "H3'"  5FU 31 
5FU H3T    H3T  H 0 1 N Y N 25.062 55.904 122.303 3.447  -0.153 1.628  H3T    5FU 32 
5FU H6     H6   H 0 1 N N N 28.320 52.014 122.801 0.918  2.005  -1.808 H6     5FU 33 
5FU H3     H3   H 0 1 N N N 31.381 53.458 125.654 -1.714 4.851  1.049  H3     5FU 34 
# 
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 
5FU F5    C5     SING N N 1  
5FU C5    C6     DOUB N N 2  
5FU C5    C4     SING N N 3  
5FU C4    O4     DOUB N N 4  
5FU C4    N3     SING N N 5  
5FU N3    H3     SING N N 6  
5FU N3    C2     SING N N 7  
5FU C2    N1     SING N N 8  
5FU C2    O2     DOUB N N 9  
5FU C6    N1     SING N N 10 
5FU C6    H6     SING N N 11 
5FU N1    "C1'"  SING N N 12 
5FU "C1'" "C2'"  SING N N 13 
5FU "C1'" "H1'"  SING N N 14 
5FU "C1'" "O4'"  SING N N 15 
5FU "O4'" "C4'"  SING N N 16 
5FU "C2'" "O2'"  SING N N 17 
5FU "C2'" "H2'"  SING N N 18 
5FU "C2'" "C3'"  SING N N 19 
5FU "O2'" "HO'2" SING N N 20 
5FU "C3'" "C4'"  SING N N 21 
5FU "C3'" "H3'"  SING N N 22 
5FU "C3'" "O3'"  SING N N 23 
5FU "O3'" H3T    SING N N 24 
5FU "C4'" "H4'"  SING N N 25 
5FU "C4'" "C5'"  SING N N 26 
5FU "C5'" "H5'1" SING N N 27 
5FU "C5'" "H5'2" SING N N 28 
5FU "C5'" "O5'"  SING N N 29 
5FU "O5'" P      SING N N 30 
5FU P     O1P    DOUB N N 31 
5FU P     O2P    SING N N 32 
5FU P     O3P    SING N N 33 
5FU O2P   HOP2   SING N N 34 
5FU O3P   HOP3   SING N N 35 
# 
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 
5FU SMILES           ACDLabs              10.04 "FC=1C(=O)NC(=O)N(C=1)C2OC(C(O)C2O)COP(=O)(O)O"                                                                                                       
5FU SMILES_CANONICAL CACTVS               3.341 "O[C@H]1[C@@H](O)[C@@H](O[C@@H]1CO[P](O)(O)=O)N2C=C(F)C(=O)NC2=O"                                                                                     
5FU SMILES           CACTVS               3.341 "O[CH]1[CH](O)[CH](O[CH]1CO[P](O)(O)=O)N2C=C(F)C(=O)NC2=O"                                                                                            
5FU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)F"                                                                                    
5FU SMILES           "OpenEye OEToolkits" 1.5.0 "C1=C(C(=O)NC(=O)N1C2C(C(C(O2)COP(=O)(O)O)O)O)F"                                                                                                      
5FU InChI            InChI                1.03  "InChI=1S/C9H12FN2O9P/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(21-8)2-20-22(17,18)19/h1,4-6,8,13-14H,2H2,(H,11,15,16)(H2,17,18,19)/t4-,5-,6-,8-/m1/s1" 
5FU InChIKey         InChI                1.03  RNBMPPYRHNWTMA-UAKXSSHOSA-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 
5FU "SYSTEMATIC NAME" ACDLabs              10.04 
;5-fluorouridine 5'-(dihydrogen phosphate)
;
5FU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
5FU "Create component"  2007-02-02 RCSB 
5FU "Modify descriptor" 2011-06-04 RCSB 
# 
