data_UPU
# 
_chem_comp.id                                    UPU 
_chem_comp.name                                  
"[(2R,3S,4R,5R)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL]METHYL (2R,3S,4R,5R)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-4-HYDROXY-2-(HYDROXYMETHYL)TETRAHYDROFURAN-3-YL HYDROGEN (S)-PHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H23 N4 O14 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-05-24 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        550.367 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UPU 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "Corina V3.40" 
_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 
UPU O2A    O2A  O 0 1 N N N 28.613 19.251 -50.670 5.858  1.892  -2.231 O2A    UPU 1  
UPU C2A    C2A  C 0 1 N N N 28.450 20.461 -50.578 5.787  2.169  -1.049 C2A    UPU 2  
UPU N3A    N3A  N 0 1 N N N 29.531 21.211 -50.846 6.163  3.391  -0.630 N3A    UPU 3  
UPU C4A    C4A  C 0 1 N N N 29.468 22.564 -50.748 6.090  3.714  0.677  C4A    UPU 4  
UPU O4A    O4A  O 0 1 N N N 30.582 23.314 -51.006 6.430  4.819  1.057  O4A    UPU 5  
UPU C5A    C5A  C 0 1 N N N 28.268 23.176 -50.406 5.613  2.755  1.603  C5A    UPU 6  
UPU C6A    C6A  C 0 1 N N N 27.158 22.358 -50.151 5.241  1.537  1.156  C6A    UPU 7  
UPU N1A    N1A  N 0 1 N N N 27.254 21.000 -50.242 5.327  1.251  -0.180 N1A    UPU 8  
UPU "C1'A" C1*A C 0 0 N N R 26.078 20.142 -49.957 4.919  -0.069 -0.667 "C1'A" UPU 9  
UPU "O4'A" O4*A O 0 0 N N N 24.850 20.812 -50.218 3.576  -0.373 -0.231 "O4'A" UPU 10 
UPU "C2'A" C2*A C 0 0 N N R 26.069 19.886 -48.455 5.798  -1.171 -0.034 "C2'A" UPU 11 
UPU "O2'A" O2*A O 0 0 N N N 25.648 18.543 -48.162 6.838  -1.561 -0.934 "O2'A" UPU 12 
UPU "C3'A" C3*A C 0 0 N N S 25.109 20.917 -47.903 4.819  -2.343 0.202  "C3'A" UPU 13 
UPU "O3'A" O3*A O 0 0 N N N 24.519 20.568 -46.640 5.224  -3.492 -0.544 "O3'A" UPU 14 
UPU "C4'A" C4*A C 0 0 N N R 24.090 20.921 -49.004 3.465  -1.811 -0.316 "C4'A" UPU 15 
UPU "C5'A" C5*A C 0 0 N N N 23.182 22.149 -48.903 2.322  -2.310 0.572  "C5'A" UPU 16 
UPU "O5'A" O5*A O 0 0 N N N 23.892 23.243 -49.447 1.076  -1.842 0.051  "O5'A" UPU 17 
UPU P      P    P 0 1 N N S 23.321 24.691 -49.835 -0.342 -2.178 0.736  P      UPU 18 
UPU O1     O1   O 0 1 N N N 22.044 25.033 -49.057 -0.618 -3.762 0.649  O1     UPU 19 
UPU O2     O2   O 0 1 N N N 24.561 25.538 -49.630 -0.315 -1.760 2.155  O2     UPU 20 
UPU "O3'B" O3*B O 0 0 N N N 22.891 24.593 -51.398 -1.512 -1.386 -0.036 "O3'B" UPU 21 
UPU "C3'B" C3*B C 0 0 N N S 23.747 24.050 -52.407 -2.874 -1.394 0.397  "C3'B" UPU 22 
UPU "C4'B" C4*B C 0 0 N N R 23.796 24.819 -53.715 -3.789 -1.947 -0.713 "C4'B" UPU 23 
UPU "C5'B" C5*B C 0 0 N N N 24.615 26.104 -53.729 -4.518 -3.195 -0.213 "C5'B" UPU 24 
UPU "O5'B" O5*B O 0 0 N N N 25.820 25.997 -52.950 -5.273 -3.767 -1.283 "O5'B" UPU 25 
UPU "O4'B" O4*B O 0 0 N N N 24.404 23.880 -54.595 -4.742 -0.919 -1.031 "O4'B" UPU 26 
UPU "C2'B" C2*B C 0 0 N N R 23.392 22.642 -52.889 -3.379 0.051  0.622  "C2'B" UPU 27 
UPU "O2'B" O2*B O 0 0 N N N 22.004 22.475 -53.162 -2.285 0.952  0.802  "O2'B" UPU 28 
UPU "C1'B" C1*B C 0 0 N N R 24.142 22.527 -54.209 -4.124 0.345  -0.705 "C1'B" UPU 29 
UPU N1B    N1B  N 0 1 N N N 25.431 21.818 -54.080 -5.141 1.380  -0.508 N1B    UPU 30 
UPU C2B    C2B  C 0 1 N N N 25.487 20.463 -54.003 -6.142 1.174  0.367  C2B    UPU 31 
UPU O2B    O2B  O 0 1 N N N 24.436 19.787 -54.017 -6.190 0.129  0.986  O2B    UPU 32 
UPU C6B    C6B  C 0 1 N N N 26.580 22.541 -54.041 -5.062 2.551  -1.212 C6B    UPU 33 
UPU C5B    C5B  C 0 1 N N N 27.824 21.915 -53.914 -5.999 3.506  -1.030 C5B    UPU 34 
UPU C4B    C4B  C 0 1 N N N 27.847 20.517 -53.837 -7.049 3.274  -0.110 C4B    UPU 35 
UPU N3B    N3B  N 0 1 N N N 26.683 19.807 -53.888 -7.089 2.109  0.568  N3B    UPU 36 
UPU O4B    O4B  O 0 1 N N N 28.937 19.923 -53.728 -7.906 4.120  0.072  O4B    UPU 37 
UPU HN3A   HN3A H 0 0 N N N 30.387 20.771 -51.119 6.489  4.043  -1.271 HN3A   UPU 38 
UPU H5A    H5A  H 0 1 N N N 28.193 24.251 -50.339 5.548  2.995  2.654  H5A    UPU 39 
UPU H6A    H6A  H 0 1 N N N 26.215 22.809 -49.879 4.875  0.793  1.847  H6A    UPU 40 
UPU "H1'A" H1*A H 0 0 N N N 26.156 19.240 -50.582 4.983  -0.109 -1.754 "H1'A" UPU 41 
UPU H2AC   CH2A H 0 0 N N N 27.068 19.978 -48.003 6.221  -0.827 0.910  H2AC   UPU 42 
UPU H2AO   OH2A H 0 0 N N N 25.555 18.056 -48.972 7.420  -2.250 -0.587 H2AO   UPU 43 
UPU H3AC   CH3A H 0 0 N N N 25.585 21.881 -47.673 4.756  -2.579 1.264  H3AC   UPU 44 
UPU H3AO   OH3A H 0 0 N N N 25.200 20.491 -45.982 6.096  -3.832 -0.301 H3AO   UPU 45 
UPU "H4'A" H4*A H 0 0 N N N 23.378 20.084 -48.952 3.306  -2.119 -1.349 "H4'A" UPU 46 
UPU "H'A1" 1H*A H 0 0 N N N 22.252 21.981 -49.467 2.323  -3.400 0.587  "H'A1" UPU 47 
UPU "H'A2" 2H*A H 0 0 N N N 22.909 22.345 -47.856 2.458  -1.932 1.585  "H'A2" UPU 48 
UPU HO1    HO1  H 0 1 N N N 22.246 25.104 -48.131 -0.648 -4.107 -0.254 HO1    UPU 49 
UPU H3BC   CH3B H 0 0 N N N 24.694 24.090 -51.848 -2.980 -1.984 1.308  H3BC   UPU 50 
UPU "H4'B" H4*B H 0 0 N N N 22.785 25.169 -53.969 -3.197 -2.189 -1.595 "H4'B" UPU 51 
UPU "H'B1" 1H*B H 0 0 N N N 24.891 26.330 -54.769 -3.789 -3.922 0.146  "H'B1" UPU 52 
UPU "H'B2" 2H*B H 0 0 N N N 23.998 26.901 -53.287 -5.190 -2.922 0.601  "H'B2" UPU 53 
UPU "H5'B" H5*B H 0 0 N N N 26.572 25.973 -53.530 -5.762 -4.564 -1.037 "H5'B" UPU 54 
UPU H2BC   CH2B H 0 0 N N N 23.649 21.894 -52.124 -4.063 0.097  1.470  H2BC   UPU 55 
UPU H2BO   OH2B H 0 0 N N N 21.522 22.438 -52.344 -2.551 1.871  0.946  H2BO   UPU 56 
UPU "H1'B" H1*B H 0 0 N N N 23.545 21.954 -54.934 -3.420 0.640  -1.484 "H1'B" UPU 57 
UPU H6B    H6B  H 0 1 N N N 26.532 23.618 -54.109 -4.253 2.711  -1.910 H6B    UPU 58 
UPU H5B    H5B  H 0 1 N N N 28.737 22.491 -53.877 -5.948 4.435  -1.579 H5B    UPU 59 
UPU HN3B   HN3B H 0 0 N N N 26.704 18.808 -53.841 -7.803 1.944  1.204  HN3B   UPU 60 
# 
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 
UPU O2A    C2A    DOUB N N 1  
UPU C2A    N3A    SING N N 2  
UPU C2A    N1A    SING N N 3  
UPU N3A    C4A    SING N N 4  
UPU N3A    HN3A   SING N N 5  
UPU C4A    O4A    DOUB N N 6  
UPU C4A    C5A    SING N N 7  
UPU C5A    C6A    DOUB N N 8  
UPU C5A    H5A    SING N N 9  
UPU C6A    N1A    SING N N 10 
UPU C6A    H6A    SING N N 11 
UPU N1A    "C1'A" SING N N 12 
UPU "C1'A" "O4'A" SING N N 13 
UPU "C1'A" "C2'A" SING N N 14 
UPU "C1'A" "H1'A" SING N N 15 
UPU "O4'A" "C4'A" SING N N 16 
UPU "C2'A" "O2'A" SING N N 17 
UPU "C2'A" "C3'A" SING N N 18 
UPU "C2'A" H2AC   SING N N 19 
UPU "O2'A" H2AO   SING N N 20 
UPU "C3'A" "C4'A" SING N N 21 
UPU "C3'A" "O3'A" SING N N 22 
UPU "C3'A" H3AC   SING N N 23 
UPU "O3'A" H3AO   SING N N 24 
UPU "C4'A" "C5'A" SING N N 25 
UPU "C4'A" "H4'A" SING N N 26 
UPU "C5'A" "O5'A" SING N N 27 
UPU "C5'A" "H'A1" SING N N 28 
UPU "C5'A" "H'A2" SING N N 29 
UPU "O5'A" P      SING N N 30 
UPU P      "O3'B" SING N N 31 
UPU P      O2     DOUB N N 32 
UPU P      O1     SING N N 33 
UPU O1     HO1    SING N N 34 
UPU "O3'B" "C3'B" SING N N 35 
UPU "C3'B" "C4'B" SING N N 36 
UPU "C3'B" "C2'B" SING N N 37 
UPU "C3'B" H3BC   SING N N 38 
UPU "C4'B" "O4'B" SING N N 39 
UPU "C4'B" "C5'B" SING N N 40 
UPU "C4'B" "H4'B" SING N N 41 
UPU "C5'B" "O5'B" SING N N 42 
UPU "C5'B" "H'B1" SING N N 43 
UPU "C5'B" "H'B2" SING N N 44 
UPU "O5'B" "H5'B" SING N N 45 
UPU "O4'B" "C1'B" SING N N 46 
UPU "C2'B" "C1'B" SING N N 47 
UPU "C2'B" "O2'B" SING N N 48 
UPU "C2'B" H2BC   SING N N 49 
UPU "O2'B" H2BO   SING N N 50 
UPU "C1'B" N1B    SING N N 51 
UPU "C1'B" "H1'B" SING N N 52 
UPU N1B    C6B    SING N N 53 
UPU N1B    C2B    SING N N 54 
UPU C2B    O2B    DOUB N N 55 
UPU C2B    N3B    SING N N 56 
UPU C6B    C5B    DOUB N N 57 
UPU C6B    H6B    SING N N 58 
UPU C5B    C4B    SING N N 59 
UPU C5B    H5B    SING N N 60 
UPU C4B    N3B    SING N N 61 
UPU C4B    O4B    DOUB N N 62 
UPU N3B    HN3B   SING N N 63 
# 
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 
UPU SMILES           ACDLabs              10.04 O=C1C=CN(C(=O)N1)C4OC(CO)C(OP(=O)(O)OCC3OC(N2C(=O)NC(=O)C=C2)C(O)C3O)C4O 
UPU InChI            InChI                1.02b 
InChI=1/C18H23N4O14P/c23-5-7-14(13(28)16(34-7)22-4-2-10(25)20-18(22)30)36-37(31,32)33-6-8-11(26)12(27)15(35-8)21-3-1-9(24)19-17(21)29/h1-4,7-8,11-16,23,26-28H,5-6H2,(H,31,32)(H,19,24,29)(H,20,25,30)/t7-,8-,11-,12-,13-,14-,15-,16-/m1/s1/f/h19-20,31H 
UPU InChIKey         InChI                1.02b KXSPLNAXPMVUEC-JGBRUXBJDJ 
UPU SMILES_CANONICAL CACTVS               3.341 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)N4C=CC(=O)NC4=O 
UPU SMILES           CACTVS               3.341 OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)N4C=CC(=O)NC4=O 
UPU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@](=O)(O)O[C@@H]3[C@H](O[C@H]([C@@H]3O)N4C=CC(=O)NC4=O)CO)O)O 
UPU SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OC3C(OC(C3O)N4C=CC(=O)NC4=O)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 
UPU "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl hydrogen (S)-phosphate (non-preferred name)" 
UPU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate" 
# 
