data_AR3
# 
_chem_comp.id                                    AR3 
_chem_comp.name                                  CYTARABINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C9 H13 N3 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "1-BETA-D-ARABINOFURANOSYLCYTOSINE; ARA-C" 
_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                        243.217 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AR3 
_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        1P5Z 
_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 
AR3 "O5'"  "O5'"  O 0 1 N N N 69.603 37.846 20.126 2.451  -0.671 -3.603 "O5'"  AR3 1  
AR3 "C5'"  "C5'"  C 0 1 N N N 70.084 37.180 21.290 1.339  0.221  -3.527 "C5'"  AR3 2  
AR3 "C4'"  "C4'"  C 0 1 N N R 70.191 35.672 21.069 0.268  -0.373 -2.610 "C4'"  AR3 3  
AR3 "O4'"  "O4'"  O 0 1 N N N 68.908 35.015 20.820 0.789  -0.546 -1.274 "O4'"  AR3 4  
AR3 "C1'"  "C1'"  C 0 1 N N R 68.945 34.157 19.690 -0.372 -0.624 -0.420 "C1'"  AR3 5  
AR3 N1     N1     N 0 1 Y N N 67.581 34.094 19.091 -0.009 -0.311 0.963  N1     AR3 6  
AR3 C6     C6     C 0 1 Y N N 66.781 35.110 19.044 1.077  0.469  1.219  C6     AR3 7  
AR3 C5     C5     C 0 1 Y N N 65.581 35.014 18.562 1.399  0.757  2.503  C5     AR3 8  
AR3 C4     C4     C 0 1 Y N N 65.145 33.836 18.102 0.605  0.228  3.541  C4     AR3 9  
AR3 N3     N3     N 0 1 Y N N 65.955 32.800 18.065 -0.443 -0.527 3.244  N3     AR3 10 
AR3 C2     C2     C 0 1 Y N N 67.182 32.939 18.562 -0.750 -0.796 1.976  C2     AR3 11 
AR3 O2     O2     O 0 1 N N N 67.993 31.922 18.522 -1.720 -1.494 1.729  O2     AR3 12 
AR3 N4     N4     N 0 1 N N N 63.889 33.644 17.594 0.912  0.500  4.854  N4     AR3 13 
AR3 "C2'"  "C2'"  C 0 1 N N S 70.097 34.681 18.834 -1.345 0.438  -0.975 "C2'"  AR3 14 
AR3 O1     O1     O 0 1 N N N 69.589 35.628 17.902 -1.201 1.670  -0.265 O1     AR3 15 
AR3 "C3'"  "C3'"  C 0 1 N N S 71.052 35.302 19.868 -0.912 0.609  -2.450 "C3'"  AR3 16 
AR3 "O3'"  "O3'"  O 0 1 N N N 72.081 34.348 20.236 -1.980 0.255  -3.330 "O3'"  AR3 17 
AR3 "H5'"  "H5'"  H 0 1 N N N 69.536 38.783 20.263 3.101  -0.259 -4.189 "H5'"  AR3 18 
AR3 "H5'1" "1H5'" H 0 0 N N N 71.052 37.611 21.635 0.923  0.369  -4.524 "H5'1" AR3 19 
AR3 "H5'2" "2H5'" H 0 0 N N N 69.460 37.418 22.183 1.669  1.179  -3.126 "H5'2" AR3 20 
AR3 "H4'"  "H4'"  H 0 1 N N N 70.641 35.324 22.028 -0.081 -1.326 -3.007 "H4'"  AR3 21 
AR3 "H1'"  "H1'"  H 0 1 N N N 69.166 33.082 19.886 -0.819 -1.616 -0.479 "H1'"  AR3 22 
AR3 H6     H6     H 0 1 N N N 67.131 36.084 19.425 1.673  0.859  0.407  H6     AR3 23 
AR3 H5     H5     H 0 1 N N N 64.944 35.914 18.543 2.256  1.374  2.728  H5     AR3 24 
AR3 HN41   1HN4   H 0 0 N N N 63.556 32.745 17.243 0.361  0.138  5.566  HN41   AR3 25 
AR3 HN42   2HN4   H 0 0 N N N 63.755 34.328 16.849 1.682  1.050  5.068  HN42   AR3 26 
AR3 "H2'"  "H2'"  H 0 1 N N N 70.618 33.909 18.220 -2.375 0.084  -0.918 "H2'"  AR3 27 
AR3 HO1    HO1    H 0 1 N N N 70.305 35.953 17.369 -1.785 2.310  -0.694 HO1    AR3 28 
AR3 "H3'"  "H3'"  H 0 1 N N N 71.574 36.199 19.462 -0.586 1.631  -2.637 "H3'"  AR3 29 
AR3 H1     H1     H 0 1 N N N 72.617 34.117 19.487 -1.634 0.322  -4.231 H1     AR3 30 
# 
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 
AR3 "O5'" "C5'"  SING N N 1  
AR3 "O5'" "H5'"  SING N N 2  
AR3 "C5'" "C4'"  SING N N 3  
AR3 "C5'" "H5'1" SING N N 4  
AR3 "C5'" "H5'2" SING N N 5  
AR3 "C4'" "O4'"  SING N N 6  
AR3 "C4'" "C3'"  SING N N 7  
AR3 "C4'" "H4'"  SING N N 8  
AR3 "O4'" "C1'"  SING N N 9  
AR3 "C1'" N1     SING N N 10 
AR3 "C1'" "C2'"  SING N N 11 
AR3 "C1'" "H1'"  SING N N 12 
AR3 N1    C6     SING Y N 13 
AR3 N1    C2     SING Y N 14 
AR3 C6    C5     DOUB Y N 15 
AR3 C6    H6     SING N N 16 
AR3 C5    C4     SING Y N 17 
AR3 C5    H5     SING N N 18 
AR3 C4    N3     DOUB Y N 19 
AR3 C4    N4     SING N N 20 
AR3 N3    C2     SING Y N 21 
AR3 C2    O2     DOUB N N 22 
AR3 N4    HN41   SING N N 23 
AR3 N4    HN42   SING N N 24 
AR3 "C2'" O1     SING N N 25 
AR3 "C2'" "C3'"  SING N N 26 
AR3 "C2'" "H2'"  SING N N 27 
AR3 O1    HO1    SING N N 28 
AR3 "C3'" "O3'"  SING N N 29 
AR3 "C3'" "H3'"  SING N N 30 
AR3 "O3'" H1     SING N N 31 
# 
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 
AR3 SMILES           ACDLabs              10.04 O=C1N=C(N)C=CN1C2OC(C(O)C2O)CO                                                                                                  
AR3 InChI            InChI                1.02b InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1/f/h10H2 
AR3 InChIKey         InChI                1.02b UHDGCWIWMRVCDJ-JEMZYTBMDI                                                                                                       
AR3 SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O                                                                             
AR3 SMILES           CACTVS               3.341 NC1=NC(=O)N(C=C1)[CH]2O[CH](CO)[CH](O)[CH]2O                                                                                    
AR3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O                                                                             
AR3 SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)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 
AR3 "SYSTEMATIC NAME" ACDLabs              10.04 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one                                
AR3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one 
# 
