data_5IC
# 
_chem_comp.id                                    5IC 
_chem_comp.name                                  "5-IODO-CYTIDINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C9 H13 I N3 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               C 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-05-13 
_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                        449.093 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     5IC 
_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        ? 
_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 
5IC "O2'"  O2*  O 0 1 N N N ?      ?      ?      1.026  0.515  -1.704 "O2'"  5IC 1  
5IC "C2'"  C2*  C 0 1 N N S -0.002 14.342 38.063 0.961  0.440  -0.285 "C2'"  5IC 2  
5IC "C3'"  C3*  C 0 1 N N S -1.307 13.736 37.557 2.168  -0.326 0.213  "C3'"  5IC 3  
5IC "O3'"  O3*  O 0 1 N N N -1.696 12.570 38.284 1.912  -0.804 1.532  "O3'"  5IC 4  
5IC "C4'"  C4*  C 0 1 N N R -0.993 13.317 36.118 3.261  0.741  0.292  "C4'"  5IC 5  
5IC "O4'"  O4*  O 0 1 N N N 0.410  13.602 35.919 2.597  2.020  0.362  "O4'"  5IC 6  
5IC "C1'"  C1*  C 0 1 N N R 1.019  13.658 37.177 1.180  1.804  0.351  "C1'"  5IC 7  
5IC N1     N1   N 0 1 N N N 2.302  14.350 37.013 0.531  2.882  -0.332 N1     5IC 8  
5IC C6     C6   C 0 1 N N N 2.373  15.707 36.809 1.154  3.517  -1.398 C6     5IC 9  
5IC C5     C5   C 0 1 N N N 3.564  16.321 36.641 0.603  4.528  -2.075 C5     5IC 10 
5IC I      I    I 0 1 N N N 3.652  18.357 36.148 1.535  5.445  -3.638 I      5IC 11 
5IC C4     C4   C 0 1 N N N 4.748  15.504 36.723 -0.757 4.954  -1.614 C4     5IC 12 
5IC N3     N3   N 0 1 N N N 4.675  14.184 36.921 -1.353 4.361  -0.609 N3     5IC 13 
5IC C2     C2   C 0 1 N N N 3.473  13.582 37.055 -0.757 3.317  0.071  C2     5IC 14 
5IC O2     O2   O 0 1 N N N 3.367  12.345 37.212 -1.340 2.777  1.013  O2     5IC 15 
5IC N4     N4   N 0 1 N N N 5.952  16.046 36.620 -1.412 5.989  -2.245 N4     5IC 16 
5IC "C5'"  C5*  C 0 1 N N N -1.811 14.078 35.107 4.178  0.759  -0.923 "C5'"  5IC 17 
5IC "O5'"  O5*  O 0 1 N N N -1.727 15.474 35.378 5.140  1.786  -0.752 "O5'"  5IC 18 
5IC P      P    P 0 1 N N N -2.283 16.517 34.319 6.242  2.013  -1.916 P      5IC 19 
5IC OP1    O1P  O 0 1 N N N -1.936 17.886 34.810 7.221  3.120  -1.655 OP1    5IC 20 
5IC OP3    O3P  O 0 1 N Y N ?      ?      ?      5.354  2.178  -3.258 OP3    5IC 21 
5IC OP2    O2P  O 0 1 N N N -3.694 16.177 34.050 6.899  0.545  -2.084 OP2    5IC 22 
5IC "HO2'" 2HO* H 0 0 N N N 0.813  0.378  0.315  1.763  -0.054 -1.980 "HO2'" 5IC 23 
5IC "H2'"  H2*  H 0 1 N N N 0.089  14.947 38.995 -0.001 0.003  -0.002 "H2'"  5IC 24 
5IC "H3'"  H3*  H 0 1 N N N -2.141 14.469 37.662 2.451  -1.179 -0.411 "H3'"  5IC 25 
5IC "HO3'" H3T  H 0 0 N Y N -2.509 12.193 37.969 1.393  -0.117 1.978  "HO3'" 5IC 26 
5IC "H4'"  H4*  H 0 1 N N N -1.239 12.239 35.973 3.870  0.634  1.195  "H4'"  5IC 27 
5IC "H1'"  H1*  H 0 1 N N N 1.279  12.681 37.648 0.838  1.814  1.392  "H1'"  5IC 28 
5IC H6     H6   H 0 1 N N N 1.454  16.317 36.780 2.137  3.128  -1.646 H6     5IC 29 
5IC H41    1H4  H 0 1 N N N 6.028  16.788 37.316 -2.190 6.395  -1.785 H41    5IC 30 
5IC H42    2H4  H 0 1 N N N 6.790  15.468 36.678 -1.076 6.280  -3.130 H42    5IC 31 
5IC "H5'"  1H5* H 0 1 N N N -2.866 13.721 35.065 3.600  0.957  -1.828 "H5'"  5IC 32 
5IC "H5''" 2H5* H 0 0 N N N -1.517 13.835 34.059 4.691  -0.199 -1.021 "H5''" 5IC 33 
5IC HOP3   3HOP H 0 0 N N N -0.333 0.624  -0.634 5.805  2.397  -4.101 HOP3   5IC 34 
5IC HOP2   2HOP H 0 0 N N N -4.027 16.801 33.416 7.671  0.436  -2.678 HOP2   5IC 35 
# 
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 
5IC "O2'" "C2'"  SING N N 1  
5IC "O2'" "HO2'" SING N N 2  
5IC "C2'" "C3'"  SING N N 3  
5IC "C2'" "C1'"  SING N N 4  
5IC "C2'" "H2'"  SING N N 5  
5IC "C3'" "O3'"  SING N N 6  
5IC "C3'" "C4'"  SING N N 7  
5IC "C3'" "H3'"  SING N N 8  
5IC "O3'" "HO3'" SING N N 9  
5IC "C4'" "O4'"  SING N N 10 
5IC "C4'" "C5'"  SING N N 11 
5IC "C4'" "H4'"  SING N N 12 
5IC "O4'" "C1'"  SING N N 13 
5IC "C1'" N1     SING N N 14 
5IC "C1'" "H1'"  SING N N 15 
5IC N1    C6     SING N N 16 
5IC N1    C2     SING N N 17 
5IC C6    C5     DOUB N N 18 
5IC C6    H6     SING N N 19 
5IC C5    I      SING N N 20 
5IC C5    C4     SING N N 21 
5IC C4    N3     DOUB N N 22 
5IC C4    N4     SING N N 23 
5IC N3    C2     SING N N 24 
5IC C2    O2     DOUB N N 25 
5IC N4    H41    SING N N 26 
5IC N4    H42    SING N N 27 
5IC "C5'" "O5'"  SING N N 28 
5IC "C5'" "H5'"  SING N N 29 
5IC "C5'" "H5''" SING N N 30 
5IC "O5'" P      SING N N 31 
5IC P     OP1    DOUB N N 32 
5IC P     OP3    SING N N 33 
5IC P     OP2    SING N N 34 
5IC OP3   HOP3   SING N N 35 
5IC OP2   HOP2   SING N N 36 
# 
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 
5IC SMILES           ACDLabs              10.04 "IC=1C(=NC(=O)N(C=1)C2OC(C(O)C2O)COP(=O)(O)O)N"                                                                                                                      
5IC InChI            InChI                1.02b "InChI=1/C9H13IN3O8P/c10-3-1-13(9(16)12-7(3)11)8-6(15)5(14)4(21-8)2-20-22(17,18)19/h1,4-6,8,14-15H,2H2,(H2,11,12,16)(H2,17,18,19)/t4-,5-,6?,8-/m1/s1/f/h17-18H,11H2" 
5IC InChIKey         InChI                1.02b CIUBKYYOJNFMQN-LGXKZKRSDX                                                                                                                                            
5IC SMILES_CANONICAL CACTVS               3.341 "NC1=NC(=O)N(C=C1I)[C@@H]2O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@@H]2O"                                                                                                    
5IC SMILES           CACTVS               3.341 "NC1=NC(=O)N(C=C1I)[CH]2O[CH](CO[P](O)(O)=O)[CH](O)[CH]2O"                                                                                                           
5IC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1=C(C(=NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)I"                                                                                                    
5IC SMILES           "OpenEye OEToolkits" 1.5.0 "C1=C(C(=NC(=O)N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)I"                                                                                                                     
# 
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 
5IC "SYSTEMATIC NAME" ACDLabs              10.04 "4-amino-5-iodo-1-(5-O-phosphono-beta-D-arabinofuranosyl)pyrimidin-2(1H)-one"                                  
5IC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4S,5R)-5-(4-amino-5-iodo-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
