data_U3S
# 
_chem_comp.id                                    U3S 
_chem_comp.name                                  1-(5-deoxy-5-piperidin-1-yl-alpha-L-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H21 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                        311.334 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     U3S 
_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        3D6Q 
_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 
U3S C4     C4     C 0 1 N N N 34.834 -4.586 12.460 -3.977 1.891  -0.115 C4     U3S 1  
U3S C5     C5     C 0 1 N N N 36.012 -4.501 13.197 -4.057 1.234  1.137  C5     U3S 2  
U3S C6     C6     C 0 1 N N N 36.826 -3.376 13.062 -3.121 0.315  1.457  C6     U3S 3  
U3S N1     N1     N 0 1 N N N 36.461 -2.309 12.202 -2.115 0.036  0.572  N1     U3S 4  
U3S N3     N3     N 0 1 N N N 34.469 -3.552 11.598 -2.970 1.588  -0.958 N3     U3S 5  
U3S CAV    CAV    C 0 1 N N N 43.496 -2.552 14.113 4.991  2.198  -0.086 CAV    U3S 6  
U3S CAK    CAK    C 0 1 N N N 42.291 -3.503 14.175 3.714  2.151  -0.930 CAK    U3S 7  
U3S CAM    CAM    C 0 1 N N N 40.941 -2.763 14.045 3.251  0.699  -1.065 CAM    U3S 8  
U3S CAJ    CAJ    C 0 1 N N N 43.407 -1.453 15.185 4.715  1.564  1.280  CAJ    U3S 9  
U3S CAL    CAL    C 0 1 N N N 41.951 -1.179 15.587 4.222  0.129  1.080  CAL    U3S 10 
U3S NBA    NBA    N 0 1 N N N 41.036 -1.337 14.435 2.999  0.138  0.268  NBA    U3S 11 
U3S "C5'"  "C5'"  C 0 1 N N N 39.765 -0.766 14.925 2.421  -1.209 0.172  "C5'"  U3S 12 
U3S "C4'"  "C4'"  C 0 1 N N S 38.533 -0.832 13.970 0.947  -1.104 -0.227 "C4'"  U3S 13 
U3S "O4'"  "O4'"  O 0 1 N N N 38.660 -1.368 12.615 0.208  -0.391 0.778  "O4'"  U3S 14 
U3S "C3'"  "C3'"  C 0 1 N N R 38.007 0.547  13.641 0.303  -2.512 -0.280 "C3'"  U3S 15 
U3S "O3'"  "O3'"  O 0 1 N N N 37.474 1.243  14.758 0.495  -3.118 -1.560 "O3'"  U3S 16 
U3S "C2'"  "C2'"  C 0 1 N N R 36.873 0.211  12.704 -1.191 -2.162 -0.045 "C2'"  U3S 17 
U3S "O2'"  "O2'"  O 0 1 N N N 36.875 1.295  11.773 -1.880 -3.254 0.567  "O2'"  U3S 18 
U3S "C1'"  "C1'"  C 0 1 N N R 37.343 -1.104 12.038 -1.099 -0.960 0.920  "C1'"  U3S 19 
U3S O4     O4     O 0 1 N N N 34.102 -5.569 12.556 -4.813 2.720  -0.428 O4     U3S 20 
U3S C2     C2     C 0 1 N N N 35.270 -2.408 11.466 -2.050 0.668  -0.614 C2     U3S 21 
U3S O2     O2     O 0 1 N N N 34.910 -1.512 10.708 -1.148 0.404  -1.385 O2     U3S 22 
U3S H5     H5     H 0 1 N N N 36.293 -5.299 13.868 -4.856 1.464  1.826  H5     U3S 23 
U3S H6     H6     H 0 1 N N N 37.748 -3.317 13.621 -3.165 -0.196 2.407  H6     U3S 24 
U3S HN3    HN3    H 0 1 N N N 33.625 -3.627 11.067 -2.909 2.034  -1.818 HN3    U3S 25 
U3S HAV    HAV    H 0 1 N N N 44.415 -3.134 14.279 5.782  1.644  -0.592 HAV    U3S 26 
U3S HAVA   HAVA   H 0 0 N N N 43.504 -2.070 13.124 5.301  3.234  0.049  HAVA   U3S 27 
U3S HAK    HAK    H 0 1 N N N 42.374 -4.223 13.348 2.935  2.738  -0.444 HAK    U3S 28 
U3S HAKA   HAKA   H 0 0 N N N 42.307 -3.999 15.157 3.916  2.562  -1.919 HAKA   U3S 29 
U3S HAM    HAM    H 0 1 N N N 40.614 -2.816 12.996 2.334  0.664  -1.653 HAM    U3S 30 
U3S HAMA   HAMA   H 0 0 N N N 40.224 -3.250 14.723 4.025  0.116  -1.564 HAMA   U3S 31 
U3S HAJ    HAJ    H 0 1 N N N 43.966 -1.779 16.075 5.631  1.556  1.869  HAJ    U3S 32 
U3S HAJA   HAJA   H 0 0 N N N 43.832 -0.528 14.770 3.951  2.142  1.801  HAJA   U3S 33 
U3S HAL    HAL    H 0 1 N N N 41.659 -1.891 16.373 4.992  -0.451 0.571  HAL    U3S 34 
U3S HALA   HALA   H 0 0 N N N 41.879 -0.143 15.949 4.011  -0.320 2.051  HALA   U3S 35 
U3S "H5'"  "H5'"  H 0 1 N N N 39.494 -1.321 15.835 2.961  -1.783 -0.581 "H5'"  U3S 36 
U3S "H5'A" "H5'A" H 0 0 N N N 39.966 0.307  15.059 2.501  -1.708 1.138  "H5'A" U3S 37 
U3S "H4'"  "H4'"  H 0 1 N N N 37.923 -1.511 14.584 0.851  -0.605 -1.191 "H4'"  U3S 38 
U3S "H3'"  "H3'"  H 0 1 N N N 38.800 1.203  13.251 0.688  -3.150 0.516  "H3'"  U3S 39 
U3S "HO3'" "HO3'" H 0 0 N N N 37.355 0.638  15.481 0.108  -4.001 -1.639 "HO3'" U3S 40 
U3S "H2'"  "H2'"  H 0 1 N N N 35.871 0.086  13.141 -1.675 -1.876 -0.979 "H2'"  U3S 41 
U3S "HO2'" "HO2'" H 0 0 N N N 36.875 2.119  12.246 -1.888 -4.062 0.036  "HO2'" U3S 42 
U3S "H1'"  "H1'"  H 0 1 N N N 37.331 -0.949 10.949 -1.246 -1.296 1.946  "H1'"  U3S 43 
# 
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 
U3S C4    C5     SING N N 1  
U3S C4    N3     SING N N 2  
U3S C4    O4     DOUB N N 3  
U3S C5    C6     DOUB N N 4  
U3S C6    N1     SING N N 5  
U3S N1    "C1'"  SING N N 6  
U3S N1    C2     SING N N 7  
U3S N3    C2     SING N N 8  
U3S CAV   CAK    SING N N 9  
U3S CAV   CAJ    SING N N 10 
U3S CAK   CAM    SING N N 11 
U3S CAM   NBA    SING N N 12 
U3S CAJ   CAL    SING N N 13 
U3S CAL   NBA    SING N N 14 
U3S NBA   "C5'"  SING N N 15 
U3S "C5'" "C4'"  SING N N 16 
U3S "C4'" "O4'"  SING N N 17 
U3S "C4'" "C3'"  SING N N 18 
U3S "O4'" "C1'"  SING N N 19 
U3S "C3'" "O3'"  SING N N 20 
U3S "C3'" "C2'"  SING N N 21 
U3S "C2'" "O2'"  SING N N 22 
U3S "C2'" "C1'"  SING N N 23 
U3S C2    O2     DOUB N N 24 
U3S C5    H5     SING N N 25 
U3S C6    H6     SING N N 26 
U3S N3    HN3    SING N N 27 
U3S CAV   HAV    SING N N 28 
U3S CAV   HAVA   SING N N 29 
U3S CAK   HAK    SING N N 30 
U3S CAK   HAKA   SING N N 31 
U3S CAM   HAM    SING N N 32 
U3S CAM   HAMA   SING N N 33 
U3S CAJ   HAJ    SING N N 34 
U3S CAJ   HAJA   SING N N 35 
U3S CAL   HAL    SING N N 36 
U3S CAL   HALA   SING N N 37 
U3S "C5'" "H5'"  SING N N 38 
U3S "C5'" "H5'A" SING N N 39 
U3S "C4'" "H4'"  SING N N 40 
U3S "C3'" "H3'"  SING N N 41 
U3S "O3'" "HO3'" SING N N 42 
U3S "C2'" "H2'"  SING N N 43 
U3S "O2'" "HO2'" SING N N 44 
U3S "C1'" "H1'"  SING N N 45 
# 
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 
U3S SMILES           ACDLabs              10.04 O=C1NC(=O)N(C=C1)C2OC(C(O)C2O)CN3CCCCC3                                                                                                                         
U3S InChI            InChI                1.02b InChI=1/C14H21N3O5/c18-10-4-7-17(14(21)15-10)13-12(20)11(19)9(22-13)8-16-5-2-1-3-6-16/h4,7,9,11-13,19-20H,1-3,5-6,8H2,(H,15,18,21)/t9-,11-,12+,13+/m0/s1/f/h15H 
U3S InChIKey         InChI                1.02b PJCAMYRNNJAIMT-QYPMDNFRDI                                                                                                                                       
U3S SMILES_CANONICAL CACTVS               3.341 O[C@@H]1[C@@H](O)[C@@H](O[C@H]1CN2CCCCC2)N3C=CC(=O)NC3=O                                                                                                        
U3S SMILES           CACTVS               3.341 O[CH]1[CH](O)[CH](O[CH]1CN2CCCCC2)N3C=CC(=O)NC3=O                                                                                                               
U3S SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1CCN(CC1)C[C@H]2[C@@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O                                                                                                     
U3S SMILES           "OpenEye OEToolkits" 1.5.0 C1CCN(CC1)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 
U3S "SYSTEMATIC NAME" ACDLabs              10.04 1-(5-deoxy-5-piperidin-1-yl-alpha-L-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione        
U3S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(piperidin-1-ylmethyl)oxolan-2-yl]pyrimidine-2,4-dione 
# 
