data_U1S
# 
_chem_comp.id                                    U1S 
_chem_comp.name                                  1-{5-deoxy-5-[4-(ethoxycarbonyl)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                               "C17 H25 N3 O7" 
_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                        383.396 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     U1S 
_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        3D6O 
_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 
U1S C4     C4     C 0 1 N N N 34.421 -4.555 12.358 -3.923 -3.281 -0.056 C4     U1S 1  
U1S C5     C5     C 0 1 N N N 35.596 -4.440 13.095 -4.381 -2.647 -1.236 C5     U1S 2  
U1S C6     C6     C 0 1 N N N 36.401 -3.310 12.944 -4.030 -1.364 -1.471 C6     U1S 3  
U1S N1     N1     N 0 1 N N N 36.040 -2.267 12.054 -3.242 -0.701 -0.570 N1     U1S 4  
U1S N3     N3     N 0 1 N N N 34.052 -3.539 11.458 -3.148 -2.593 0.807  N3     U1S 5  
U1S CAV    CAV    C 0 1 N N N 43.105 -1.605 15.568 3.988  0.739  -0.053 CAV    U1S 6  
U1S CAK    CAK    C 0 1 N N N 42.512 -0.206 15.347 3.508  1.469  -1.311 CAK    U1S 7  
U1S CAM    CAM    C 0 1 N N N 41.745 -0.109 14.008 2.386  2.438  -0.936 CAM    U1S 8  
U1S CAJ    CAJ    C 0 1 N N N 42.557 -2.603 14.538 2.804  0.011  0.588  CAJ    U1S 9  
U1S CAL    CAL    C 0 1 N N N 41.035 -2.462 14.373 1.701  1.023  0.908  CAL    U1S 10 
U1S NBA    NBA    N 0 1 N N N 40.660 -1.116 13.886 1.276  1.693  -0.327 NBA    U1S 11 
U1S "C5'"  "C5'"  C 0 1 N N N 39.482 -0.636 14.630 0.125  2.571  -0.080 "C5'"  U1S 12 
U1S "C4'"  "C4'"  C 0 1 N N S 38.190 -0.722 13.784 -1.087 1.724  0.316  "C4'"  U1S 13 
U1S "O4'"  "O4'"  O 0 1 N N N 38.251 -1.303 12.436 -1.437 0.826  -0.749 "O4'"  U1S 14 
U1S "C3'"  "C3'"  C 0 1 N N R 37.639 0.641  13.448 -2.332 2.625  0.512  "C3'"  U1S 15 
U1S "O3'"  "O3'"  O 0 1 N N N 37.178 1.351  14.588 -2.391 3.140  1.844  "O3'"  U1S 16 
U1S "C2'"  "C2'"  C 0 1 N N R 36.446 0.243  12.607 -3.476 1.608  0.254  "C2'"  U1S 17 
U1S "O2'"  "O2'"  O 0 1 N N N 36.305 1.318  11.694 -4.641 2.268  -0.244 "O2'"  U1S 18 
U1S "C1'"  "C1'"  C 0 1 N N R 36.921 -1.053 11.891 -2.861 0.690  -0.825 "C1'"  U1S 19 
U1S O4     O4     O 0 1 N N N 33.713 -5.551 12.486 -4.230 -4.435 0.180  O4     U1S 20 
U1S C2     C2     C 0 1 N N N 34.854 -2.393 11.306 -2.814 -1.315 0.548  C2     U1S 21 
U1S O2     O2     O 0 1 N N N 34.504 -1.516 10.517 -2.114 -0.707 1.335  O2     U1S 22 
U1S H5     H5     H 0 1 N N N 35.884 -5.223 13.781 -5.002 -3.182 -1.939 H5     U1S 23 
U1S H6     H6     H 0 1 N N N 37.314 -3.229 13.515 -4.369 -0.864 -2.366 H6     U1S 24 
U1S HN3    HN3    H 0 1 N N N 33.213 -3.632 10.922 -2.831 -3.020 1.618  HN3    U1S 25 
U1S C15    C15    C 0 1 N N N 45.911 -4.604 14.186 7.168  -2.731 1.304  C15    U1S 26 
U1S HAV    HAV    H 0 1 N N N 42.826 -1.950 16.575 4.397  1.462  0.653  HAV    U1S 27 
U1S HAK    HAK    H 0 1 N N N 41.815 0.015  16.169 4.338  2.024  -1.748 HAK    U1S 28 
U1S HAKA   HAKA   H 0 0 N N N 43.341 0.516  15.319 3.135  0.742  -2.033 HAKA   U1S 29 
U1S HAM    HAM    H 0 1 N N N 41.296 0.893  13.939 2.763  3.173  -0.224 HAM    U1S 30 
U1S HAMA   HAMA   H 0 0 N N N 42.466 -0.300 13.199 2.032  2.949  -1.831 HAMA   U1S 31 
U1S HAJ    HAJ    H 0 1 N N N 43.038 -2.412 13.568 2.420  -0.739 -0.104 HAJ    U1S 32 
U1S HAJA   HAJA   H 0 0 N N N 42.774 -3.621 14.892 3.130  -0.476 1.507  HAJA   U1S 33 
U1S HAL    HAL    H 0 1 N N N 40.688 -3.210 13.646 0.851  0.505  1.352  HAL    U1S 34 
U1S HALA   HALA   H 0 0 N N N 40.566 -2.615 15.356 2.082  1.764  1.611  HALA   U1S 35 
U1S "H5'"  "H5'"  H 0 1 N N N 39.356 -1.258 15.529 0.363  3.264  0.726  "H5'"  U1S 36 
U1S "H5'A" "H5'A" H 0 0 N N N 39.650 0.419  14.892 -0.105 3.132  -0.986 "H5'A" U1S 37 
U1S "H4'"  "H4'"  H 0 1 N N N 37.607 -1.365 14.460 -0.875 1.166  1.228  "H4'"  U1S 38 
U1S "H3'"  "H3'"  H 0 1 N N N 38.382 1.304  12.981 -2.351 3.433  -0.220 "H3'"  U1S 39 
U1S "HO3'" "HO3'" H 0 0 N N N 37.075 0.749  15.316 -3.154 3.710  2.012  "HO3'" U1S 40 
U1S "H2'"  "H2'"  H 0 1 N N N 35.496 0.063  13.131 -3.707 1.046  1.159  "H2'"  U1S 41 
U1S "HO2'" "HO2'" H 0 0 N N N 36.273 2.138  12.172 -5.014 2.921  0.365  "HO2'" U1S 42 
U1S "H1'"  "H1'"  H 0 1 N N N 36.895 -0.889 10.804 -3.209 0.994  -1.812 "H1'"  U1S 43 
U1S C16    C16    C 0 1 N N N 45.000 -3.361 14.124 6.640  -1.961 0.092  C16    U1S 44 
U1S O6     O6     O 0 1 N N N 45.216 -2.590 15.195 5.622  -1.020 0.524  O6     U1S 45 
U1S C17    C17    C 0 1 N N N 44.637 -1.528 15.425 5.052  -0.261 -0.426 C17    U1S 46 
U1S O7     O7     O 0 1 N N N 44.904 -0.895 16.433 5.393  -0.379 -1.579 O7     U1S 47 
U1S H21    H21    H 0 1 N N N 46.128 -4.952 13.165 6.349  -3.273 1.776  H21    U1S 48 
U1S H22    H22    H 0 1 N N N 46.852 -4.344 14.692 7.933  -3.438 0.980  H22    U1S 49 
U1S H23    H23    H 0 1 N N N 45.403 -5.403 14.745 7.601  -2.031 2.019  H23    U1S 50 
U1S H24    H24    H 0 1 N N N 45.224 -2.789 13.211 7.459  -1.419 -0.380 H24    U1S 51 
U1S H25    H25    H 0 1 N N N 43.948 -3.681 14.112 6.207  -2.661 -0.623 H25    U1S 52 
# 
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 
U1S C4    C5     SING N N 1  
U1S C4    N3     SING N N 2  
U1S C4    O4     DOUB N N 3  
U1S C5    C6     DOUB N N 4  
U1S C5    H5     SING N N 5  
U1S C6    N1     SING N N 6  
U1S C6    H6     SING N N 7  
U1S N1    "C1'"  SING N N 8  
U1S N1    C2     SING N N 9  
U1S N3    C2     SING N N 10 
U1S N3    HN3    SING N N 11 
U1S CAV   CAK    SING N N 12 
U1S CAV   CAJ    SING N N 13 
U1S CAV   C17    SING N N 14 
U1S CAV   HAV    SING N N 15 
U1S CAK   CAM    SING N N 16 
U1S CAK   HAK    SING N N 17 
U1S CAK   HAKA   SING N N 18 
U1S CAM   NBA    SING N N 19 
U1S CAM   HAM    SING N N 20 
U1S CAM   HAMA   SING N N 21 
U1S CAJ   CAL    SING N N 22 
U1S CAJ   HAJ    SING N N 23 
U1S CAJ   HAJA   SING N N 24 
U1S CAL   NBA    SING N N 25 
U1S CAL   HAL    SING N N 26 
U1S CAL   HALA   SING N N 27 
U1S NBA   "C5'"  SING N N 28 
U1S "C5'" "C4'"  SING N N 29 
U1S "C5'" "H5'"  SING N N 30 
U1S "C5'" "H5'A" SING N N 31 
U1S "C4'" "O4'"  SING N N 32 
U1S "C4'" "C3'"  SING N N 33 
U1S "C4'" "H4'"  SING N N 34 
U1S "O4'" "C1'"  SING N N 35 
U1S "C3'" "O3'"  SING N N 36 
U1S "C3'" "C2'"  SING N N 37 
U1S "C3'" "H3'"  SING N N 38 
U1S "O3'" "HO3'" SING N N 39 
U1S "C2'" "O2'"  SING N N 40 
U1S "C2'" "C1'"  SING N N 41 
U1S "C2'" "H2'"  SING N N 42 
U1S "O2'" "HO2'" SING N N 43 
U1S "C1'" "H1'"  SING N N 44 
U1S C2    O2     DOUB N N 45 
U1S C15   C16    SING N N 46 
U1S C16   O6     SING N N 47 
U1S O6    C17    SING N N 48 
U1S C17   O7     DOUB N N 49 
U1S C15   H21    SING N N 50 
U1S C15   H22    SING N N 51 
U1S C15   H23    SING N N 52 
U1S C16   H24    SING N N 53 
U1S C16   H25    SING N N 54 
# 
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 
U1S SMILES           ACDLabs              10.04 O=C(OCC)C1CCN(CC1)CC3OC(N2C(=O)NC(=O)C=C2)C(O)C3O                                                                                                                                       
U1S InChI            InChI                1.02b InChI=1/C17H25N3O7/c1-2-26-16(24)10-3-6-19(7-4-10)9-11-13(22)14(23)15(27-11)20-8-5-12(21)18-17(20)25/h5,8,10-11,13-15,22-23H,2-4,6-7,9H2,1H3,(H,18,21,25)/t11-,13-,14+,15+/m0/s1/f/h18H 
U1S InChIKey         InChI                1.02b JCIDLMJUELAXRU-DYHSWNGZDZ                                                                                                                                                               
U1S SMILES_CANONICAL CACTVS               3.341 CCOC(=O)[C@H]1CCN(CC1)C[C@@H]2O[C@H]([C@H](O)[C@H]2O)N3C=CC(=O)NC3=O                                                                                                                    
U1S SMILES           CACTVS               3.341 CCOC(=O)[CH]1CCN(CC1)C[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O                                                                                                                          
U1S SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCOC(=O)C1CCN(CC1)C[C@H]2[C@@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O                                                                                                                     
U1S SMILES           "OpenEye OEToolkits" 1.5.0 CCOC(=O)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 
U1S "SYSTEMATIC NAME" ACDLabs              10.04 1-{5-deoxy-5-[4-(ethoxycarbonyl)piperidin-1-yl]-alpha-L-arabinofuranosyl}pyrimidine-2,4(1H,3H)-dione            
U1S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "ethyl 1-[[(2S,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl]piperidine-4-carboxylate" 
# 
