data_5FC
# 
_chem_comp.id                                    5FC 
_chem_comp.name                                  "5-FORMYL-2'-DEOXY-CYTIDINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H14 N3 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               DC 
_chem_comp.pdbx_synonyms                         "2'-DEOXY-5-FORMYLCYTIDINE-5'-MONOPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-04-06 
_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                        335.207 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     5FC 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1VE8 
_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 
5FC P      P    P 0 1 N N N -7.079 2.228  3.659  -3.968 -1.665 3.118  P      5FC 1  
5FC OP2    O2P  O 0 1 N N N -7.965 3.403  3.848  -3.912 -2.311 1.636  OP2    5FC 2  
5FC OP1    O1P  O 0 1 N N N -7.590 1.027  2.948  -4.406 -2.599 4.208  OP1    5FC 3  
5FC "O5'"  O5*  O 0 1 N N N -5.764 2.718  2.915  -2.493 -1.028 3.315  "O5'"  5FC 4  
5FC N1     N1   N 0 1 N N N -2.139 1.245  1.123  1.164  -2.047 0.989  N1     5FC 5  
5FC C6     C6   C 0 1 N N N -3.061 0.288  1.392  0.010  -2.813 0.936  C6     5FC 6  
5FC C2     C2   C 0 1 N N N -0.845 0.875  0.808  2.348  -2.526 0.380  C2     5FC 7  
5FC O2     O2   O 0 1 N N N -0.031 1.755  0.506  3.389  -1.869 0.412  O2     5FC 8  
5FC N3     N3   N 0 1 N N N -0.500 -0.440 0.834  2.319  -3.754 -0.256 N3     5FC 9  
5FC C4     C4   C 0 1 N N N -1.385 -1.409 1.156  1.226  -4.473 -0.303 C4     5FC 10 
5FC N4     N4   N 0 1 N N N -0.899 -2.643 1.336  1.261  -5.687 -0.952 N4     5FC 11 
5FC C5     C5   C 0 1 N N N -2.743 -1.001 1.424  -0.040 -4.000 0.328  C5     5FC 12 
5FC "C2'"  C2*  C 0 1 N N N -3.620 3.154  0.326  0.710  0.360  0.754  "C2'"  5FC 13 
5FC "C5'"  C5*  C 0 1 N N N -4.953 3.738  3.487  -2.005 -0.136 2.327  "C5'"  5FC 14 
5FC "C4'"  C4*  C 0 1 N N R -3.801 4.049  2.564  -0.611 0.328  2.728  "C4'"  5FC 15 
5FC "O4'"  O4*  O 0 1 N N N -2.891 2.930  2.531  0.247  -0.829 2.764  "O4'"  5FC 16 
5FC "C1'"  C1*  C 0 1 N N R -2.474 2.679  1.203  1.157  -0.778 1.657  "C1'"  5FC 17 
5FC "C3'"  C3*  C 0 1 N N S -4.220 4.309  1.121  0.008  1.286  1.720  "C3'"  5FC 18 
5FC "O3'"  O3*  O 0 1 N N N -3.698 5.574  0.727  0.965  2.121  2.368  "O3'"  5FC 19 
5FC C5A    C5A  C 0 1 N N N -3.780 -2.066 1.593  -1.315 -4.719 0.336  C5A    5FC 20 
5FC O5A    O5A  O 0 1 N N N -3.473 -3.256 1.626  -1.460 -5.814 -0.196 O5A    5FC 21 
5FC OP3    O3P  O 0 1 N Y N ?      ?      ?      -4.901 -0.360 2.920  OP3    5FC 22 
5FC HOP2   2HOP H 0 0 N N N -7.638 4.170  4.302  -4.684 -2.823 1.313  HOP2   5FC 23 
5FC H6     H6   H 0 1 N N N -4.108 0.568  1.592  -0.855 -2.377 1.426  H6     5FC 24 
5FC HN41   1HN4 H 0 0 N N N -1.567 -3.374 1.579  1.671  -5.721 -1.853 HN41   5FC 25 
5FC HN42   2HN4 H 0 0 N N N -0.155 -2.616 2.033  0.874  -6.473 -0.489 HN42   5FC 26 
5FC "H2'"  1H2* H 0 1 N N N -3.326 3.414  -0.717 -0.003 -0.001 0.003  "H2'"  5FC 27 
5FC "H2''" 2H2* H 0 0 N N N -4.348 2.357  0.046  1.556  0.818  0.232  "H2''" 5FC 28 
5FC "H5'"  1H5* H 0 1 N N N -5.542 4.648  3.744  -1.971 -0.654 1.366  "H5'"  5FC 29 
5FC "H5''" 2H5* H 0 0 N N N -4.608 3.474  4.514  -2.683 0.718  2.254  "H5''" 5FC 30 
5FC "H4'"  H4*  H 0 1 N N N -3.335 4.976  2.972  -0.644 0.753  3.736  "H4'"  5FC 31 
5FC "H1'"  H1*  H 0 1 N N N -1.558 3.215  0.860  2.163  -0.604 2.054  "H1'"  5FC 32 
5FC "H3'"  H3*  H 0 1 N N N -5.322 4.351  0.962  -0.722 1.941  1.236  "H3'"  5FC 33 
5FC "HO3'" H3T  H 0 0 N Y N -4.071 6.293  1.222  0.754  3.041  2.131  "HO3'" 5FC 34 
5FC H5A    H5A  H 0 1 N N N -4.872 -1.964 1.703  -2.141 -4.204 0.856  H5A    5FC 35 
5FC HOP3   3HOP H 0 0 N N N 0.567  -0.752 -0.121 -5.874 -0.475 2.871  HOP3   5FC 36 
# 
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 
5FC P     OP2    SING N N 1  
5FC P     OP1    DOUB N N 2  
5FC P     "O5'"  SING N N 3  
5FC P     OP3    SING N N 4  
5FC OP2   HOP2   SING N N 5  
5FC "O5'" "C5'"  SING N N 6  
5FC N1    C6     SING N N 7  
5FC N1    C2     SING N N 8  
5FC N1    "C1'"  SING N N 9  
5FC C6    C5     DOUB N N 10 
5FC C6    H6     SING N N 11 
5FC C2    O2     DOUB N N 12 
5FC C2    N3     SING N N 13 
5FC N3    C4     DOUB N N 14 
5FC C4    N4     SING N N 15 
5FC C4    C5     SING N N 16 
5FC N4    HN41   SING N N 17 
5FC N4    HN42   SING N N 18 
5FC C5    C5A    SING N N 19 
5FC "C2'" "C1'"  SING N N 20 
5FC "C2'" "C3'"  SING N N 21 
5FC "C2'" "H2'"  SING N N 22 
5FC "C2'" "H2''" SING N N 23 
5FC "C5'" "C4'"  SING N N 24 
5FC "C5'" "H5'"  SING N N 25 
5FC "C5'" "H5''" SING N N 26 
5FC "C4'" "O4'"  SING N N 27 
5FC "C4'" "C3'"  SING N N 28 
5FC "C4'" "H4'"  SING N N 29 
5FC "O4'" "C1'"  SING N N 30 
5FC "C1'" "H1'"  SING N N 31 
5FC "C3'" "O3'"  SING N N 32 
5FC "C3'" "H3'"  SING N N 33 
5FC "O3'" "HO3'" SING N N 34 
5FC C5A   O5A    DOUB N N 35 
5FC C5A   H5A    SING N N 36 
5FC OP3   HOP3   SING N N 37 
# 
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 
5FC SMILES           ACDLabs              10.04 "O=CC=1C(=NC(=O)N(C=1)C2OC(C(O)C2)COP(=O)(O)O)N"                                                                                                                 
5FC InChI            InChI                1.02b "InChI=1/C10H14N3O8P/c11-9-5(3-14)2-13(10(16)12-9)8-1-6(15)7(21-8)4-20-22(17,18)19/h2-3,6-8,15H,1,4H2,(H2,11,12,16)(H2,17,18,19)/t6-,7+,8+/m0/s1/f/h17-18H,11H2" 
5FC InChIKey         InChI                1.02b HDFNXAHZEYLDBJ-GHUFCVTQDJ                                                                                                                                        
5FC SMILES_CANONICAL CACTVS               3.341 "NC1=NC(=O)N(C=C1C=O)[C@H]2C[C@H](O)[C@@H](CO[P](O)(O)=O)O2"                                                                                                     
5FC SMILES           CACTVS               3.341 "NC1=NC(=O)N(C=C1C=O)[CH]2C[CH](O)[CH](CO[P](O)(O)=O)O2"                                                                                                         
5FC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)C=O)COP(=O)(O)O)O"                                                                                                       
5FC SMILES           "OpenEye OEToolkits" 1.5.0 "C1C(C(OC1N2C=C(C(=NC2=O)N)C=O)COP(=O)(O)O)O"                                                                                                                    
# 
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 
5FC "SYSTEMATIC NAME" ACDLabs              10.04 
;2'-deoxy-5-formylcytidine 5'-(dihydrogen phosphate)
;
5FC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(4-amino-5-methanoyl-2-oxo-pyrimidin-1-yl)-3-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
