data_U4S
# 
_chem_comp.id                                    U4S 
_chem_comp.name                                  1-(5-deoxy-5-pyrrolidin-1-yl-alpha-L-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H19 N3 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-06-10 
_chem_comp.pdbx_modified_date                    2009-02-06 
_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                        297.307 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     U4S 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3D7B 
_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 
U4S C4     C4     C 0 1 N N N 34.788 -4.592 12.466 -3.967 1.633  -0.127 C4     U4S 1  
U4S C5     C5     C 0 1 N N N 35.971 -4.496 13.188 -4.011 0.935  1.104  C5     U4S 2  
U4S C6     C6     C 0 1 N N N 36.771 -3.364 13.040 -2.995 0.106  1.426  C6     U4S 3  
U4S N1     N1     N 0 1 N N N 36.391 -2.305 12.184 -1.945 -0.047 0.562  N1     U4S 4  
U4S N3     N3     N 0 1 N N N 34.407 -3.558 11.602 -2.914 1.454  -0.951 N3     U4S 5  
U4S CAJ    CAJ    C 0 1 N N N 41.821 -1.033 13.649 4.469  0.641  1.061  CAJ    U4S 6  
U4S "C5'"  "C5'"  C 0 1 N N N 39.751 -0.622 14.761 2.700  -0.824 0.252  "C5'"  U4S 7  
U4S "C4'"  "C4'"  C 0 1 N N S 38.462 -0.761 13.931 1.234  -0.855 -0.184 "C4'"  U4S 8  
U4S "O4'"  "O4'"  O 0 1 N N N 38.566 -1.353 12.599 0.403  -0.248 0.819  "O4'"  U4S 9  
U4S "C3'"  "C3'"  C 0 1 N N R 37.934 0.598  13.564 0.735  -2.318 -0.290 "C3'"  U4S 10 
U4S "O3'"  "O3'"  O 0 1 N N N 37.446 1.331  14.678 1.018  -2.865 -1.580 "O3'"  U4S 11 
U4S "C2'"  "C2'"  C 0 1 N N R 36.775 0.218  12.676 -0.792 -2.124 -0.087 "C2'"  U4S 12 
U4S "O2'"  "O2'"  O 0 1 N N N 36.716 1.277  11.726 -1.383 -3.296 0.479  "O2'"  U4S 13 
U4S "C1'"  "C1'"  C 0 1 N N R 37.263 -1.093 12.012 -0.843 -0.947 0.911  "C1'"  U4S 14 
U4S O4     O4     O 0 1 N N N 34.070 -5.584 12.575 -4.873 2.382  -0.442 O4     U4S 15 
U4S C2     C2     C 0 1 N N N 35.202 -2.412 11.457 -1.916 0.621  -0.606 C2     U4S 16 
U4S O2     O2     O 0 1 N N N 34.845 -1.511 10.703 -0.973 0.470  -1.359 O2     U4S 17 
U4S CAI    CAI    C 0 1 N N N 41.337 -2.122 15.704 3.335  1.221  -0.907 CAI    U4S 18 
U4S CAG    CAG    C 0 1 N N N 42.803 -1.682 15.686 4.267  2.417  -0.614 CAG    U4S 19 
U4S CAH    CAH    C 0 1 N N N 43.105 -1.643 14.199 5.013  2.035  0.681  CAH    U4S 20 
U4S NAT    NAT    N 0 1 N N N 40.737 -1.658 14.432 3.134  0.570  0.413  NAT    U4S 21 
U4S H5     H5     H 0 1 N N N 36.268 -5.290 13.857 -4.845 1.066  1.777  H5     U4S 22 
U4S H6     H6     H 0 1 N N N 37.698 -3.295 13.589 -3.011 -0.434 2.361  H6     U4S 23 
U4S HN3    HN3    H 0 1 N N N 33.557 -3.638 11.082 -2.877 1.928  -1.797 HN3    U4S 24 
U4S HAJ    HAJ    H 0 1 N N N 41.818 0.060  13.774 5.122  -0.141 0.673  HAJ    U4S 25 
U4S HAJA   HAJA   H 0 0 N N N 41.708 -1.215 12.570 4.371  0.553  2.144  HAJA   U4S 26 
U4S "H5'"  "H5'"  H 0 1 N N N 40.196 0.363  14.555 2.809  -1.350 1.200  "H5'"  U4S 27 
U4S "H5'A" "H5'A" H 0 0 N N N 39.484 -0.733 15.822 3.315  -1.310 -0.506 "H5'A" U4S 28 
U4S "H4'"  "H4'"  H 0 1 N N N 37.860 -1.397 14.597 1.112  -0.341 -1.137 "H4'"  U4S 29 
U4S "H3'"  "H3'"  H 0 1 N N N 38.704 1.245  13.119 1.162  -2.937 0.499  "H3'"  U4S 30 
U4S "HO3'" "HO3'" H 0 0 N N N 37.337 0.747  15.419 0.723  -3.780 -1.692 "HO3'" U4S 31 
U4S "H2'"  "H2'"  H 0 1 N N N 35.794 0.078  13.154 -1.279 -1.862 -1.026 "H2'"  U4S 32 
U4S "HO2'" "HO2'" H 0 0 N N N 36.703 2.111  12.181 -1.297 -4.085 -0.073 "HO2'" U4S 33 
U4S "H1'"  "H1'"  H 0 1 N N N 37.261 -0.934 10.924 -0.982 -1.325 1.924  "H1'"  U4S 34 
U4S HAI    HAI    H 0 1 N N N 41.266 -3.217 15.784 2.383  1.570  -1.308 HAI    U4S 35 
U4S HAIA   HAIA   H 0 0 N N N 40.808 -1.694 16.568 3.810  0.530  -1.603 HAIA   U4S 36 
U4S HAG    HAG    H 0 1 N N N 42.945 -0.700 16.161 4.974  2.555  -1.432 HAG    U4S 37 
U4S HAGA   HAGA   H 0 0 N N N 43.469 -2.349 16.253 3.682  3.324  -0.461 HAGA   U4S 38 
U4S HAH    HAH    H 0 1 N N N 43.301 -2.644 13.787 4.794  2.755  1.470  HAH    U4S 39 
U4S HAHA   HAHA   H 0 0 N N N 44.014 -1.079 13.942 6.086  1.986  0.499  HAHA   U4S 40 
# 
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 
U4S C4    C5     SING N N 1  
U4S C4    N3     SING N N 2  
U4S C4    O4     DOUB N N 3  
U4S C5    C6     DOUB N N 4  
U4S C6    N1     SING N N 5  
U4S N1    "C1'"  SING N N 6  
U4S N1    C2     SING N N 7  
U4S N3    C2     SING N N 8  
U4S CAJ   CAH    SING N N 9  
U4S CAJ   NAT    SING N N 10 
U4S "C5'" "C4'"  SING N N 11 
U4S "C5'" NAT    SING N N 12 
U4S "C4'" "O4'"  SING N N 13 
U4S "C4'" "C3'"  SING N N 14 
U4S "O4'" "C1'"  SING N N 15 
U4S "C3'" "O3'"  SING N N 16 
U4S "C3'" "C2'"  SING N N 17 
U4S "C2'" "O2'"  SING N N 18 
U4S "C2'" "C1'"  SING N N 19 
U4S C2    O2     DOUB N N 20 
U4S CAI   CAG    SING N N 21 
U4S CAI   NAT    SING N N 22 
U4S CAG   CAH    SING N N 23 
U4S C5    H5     SING N N 24 
U4S C6    H6     SING N N 25 
U4S N3    HN3    SING N N 26 
U4S CAJ   HAJ    SING N N 27 
U4S CAJ   HAJA   SING N N 28 
U4S "C5'" "H5'"  SING N N 29 
U4S "C5'" "H5'A" SING N N 30 
U4S "C4'" "H4'"  SING N N 31 
U4S "C3'" "H3'"  SING N N 32 
U4S "O3'" "HO3'" SING N N 33 
U4S "C2'" "H2'"  SING N N 34 
U4S "O2'" "HO2'" SING N N 35 
U4S "C1'" "H1'"  SING N N 36 
U4S CAI   HAI    SING N N 37 
U4S CAI   HAIA   SING N N 38 
U4S CAG   HAG    SING N N 39 
U4S CAG   HAGA   SING N N 40 
U4S CAH   HAH    SING N N 41 
U4S CAH   HAHA   SING N N 42 
# 
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 
U4S SMILES           ACDLabs              10.04 O=C1NC(=O)N(C=C1)C2OC(C(O)C2O)CN3CCCC3                                                                                                                      
U4S InChI            InChI                1.02b InChI=1/C13H19N3O5/c17-9-3-6-16(13(20)14-9)12-11(19)10(18)8(21-12)7-15-4-1-2-5-15/h3,6,8,10-12,18-19H,1-2,4-5,7H2,(H,14,17,20)/t8-,10-,11+,12+/m0/s1/f/h14H 
U4S InChIKey         InChI                1.02b RPODXOXNOBCNGM-CYDXRMARDQ                                                                                                                                   
U4S SMILES_CANONICAL CACTVS               3.341 O[C@@H]1[C@@H](O)[C@@H](O[C@H]1CN2CCCC2)N3C=CC(=O)NC3=O                                                                                                     
U4S SMILES           CACTVS               3.341 O[CH]1[CH](O)[CH](O[CH]1CN2CCCC2)N3C=CC(=O)NC3=O                                                                                                            
U4S SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1CCN(C1)C[C@H]2[C@@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O                                                                                                  
U4S SMILES           "OpenEye OEToolkits" 1.5.0 C1CCN(C1)CC2C(C(C(O2)N3C=CC(=O)NC3=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 
U4S "SYSTEMATIC NAME" ACDLabs              10.04 1-(5-deoxy-5-pyrrolidin-1-yl-alpha-L-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione        
U4S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(pyrrolidin-1-ylmethyl)oxolan-2-yl]pyrimidine-2,4-dione 
# 
