data_UPG
# 
_chem_comp.id                                    UPG 
_chem_comp.name                                  "URIDINE-5'-DIPHOSPHATE-GLUCOSE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H24 N2 O17 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;URIDINE-5'-MONOPHOSPHATE GLUCOPYRANOSYL-MONOPHOSPHATE ESTER
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        566.302 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UPG 
_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        1EK6 
_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 
UPG N1     N1     N 0 1 N N N 25.413 6.752  43.956 0.916  -0.650 5.742  N1     UPG 1  
UPG C2     C2     C 0 1 N N N 24.539 6.200  44.894 1.590  0.438  5.330  C2     UPG 2  
UPG N3     N3     N 0 1 N N N 24.197 7.045  45.917 2.862  0.650  5.714  N3     UPG 3  
UPG C4     C4     C 0 1 N N N 24.620 8.374  46.083 3.487  -0.235 6.515  C4     UPG 4  
UPG C5     C5     C 0 1 N N N 25.498 8.840  45.060 2.791  -1.388 6.951  C5     UPG 5  
UPG C6     C6     C 0 1 N N N 25.855 8.055  44.059 1.514  -1.574 6.555  C6     UPG 6  
UPG O2     O2     O 0 1 N N N 24.106 5.041  44.840 1.039  1.246  4.608  O2     UPG 7  
UPG O4     O4     O 0 1 N N N 24.217 9.023  47.037 4.640  -0.046 6.859  O4     UPG 8  
UPG C1C    C1*    C 0 1 N N R 25.915 5.905  42.850 -0.469 -0.852 5.311  C1C    UPG 9  
UPG C2C    C2*    C 0 1 N N R 25.525 6.365  41.451 -1.345 0.369  5.689  C2C    UPG 10 
UPG O2C    O2*    O 0 1 N N N 24.217 5.848  41.079 -1.844 0.246  7.022  O2C    UPG 11 
UPG C3C    C3*    C 0 1 N N S 26.667 5.791  40.579 -2.498 0.274  4.656  C3C    UPG 12 
UPG C4C    C4*    C 0 1 N N R 27.850 5.881  41.532 -1.913 -0.586 3.520  C4C    UPG 13 
UPG O4C    O4*    O 0 1 N N N 27.306 5.888  42.894 -0.553 -0.894 3.871  O4C    UPG 14 
UPG O3C    O3*    O 0 1 N N N 26.435 4.438  40.151 -3.639 -0.361 5.237  O3C    UPG 15 
UPG C5C    C5*    C 0 1 N N N 28.721 7.089  41.335 -1.947 0.193  2.205  C5C    UPG 16 
UPG O5C    O5*    O 0 1 N N N 27.849 8.218  41.413 -1.396 -0.609 1.160  O5C    UPG 17 
UPG PA     PA     P 0 1 N N S 28.478 9.680  41.403 -1.463 0.269  -0.187 PA     UPG 18 
UPG O1A    O1A    O 0 1 N N N 29.568 9.872  42.372 -0.676 1.509  -0.007 O1A    UPG 19 
UPG O2A    O2A    O 0 1 N N N 27.398 10.697 41.466 -2.996 0.647  -0.505 O2A    UPG 20 
UPG O3A    O3A    O 0 1 N N N 29.280 9.741  39.973 -0.855 -0.579 -1.412 O3A    UPG 21 
UPG PB     PB     P 0 1 N N R 28.768 9.732  38.482 -0.953 0.355  -2.720 PB     UPG 22 
UPG O1B    O1B    O 0 1 N N N 27.329 9.980  38.379 -0.174 1.594  -2.500 O1B    UPG 23 
UPG O2B    O2B    O 0 1 N N N 29.251 8.422  37.941 -2.494 0.732  -2.995 O2B    UPG 24 
UPG O3B    O3B    O 0 1 N N N 29.518 10.990 37.753 -0.359 -0.435 -3.990 O3B    UPG 25 
UPG "C1'"  "C1'"  C 0 1 N N R 30.770 11.399 38.211 -0.474 0.441  -5.113 "C1'"  UPG 26 
UPG "C2'"  "C2'"  C 0 1 N N R 30.814 12.938 38.266 -0.665 -0.386 -6.385 "C2'"  UPG 27 
UPG "C3'"  "C3'"  C 0 1 N N S 30.475 13.471 36.893 0.531  -1.328 -6.553 "C3'"  UPG 28 
UPG "C4'"  "C4'"  C 0 1 N N S 31.423 12.927 35.834 1.818  -0.497 -6.503 "C4'"  UPG 29 
UPG "C5'"  "C5'"  C 0 1 N N R 31.464 11.395 35.905 1.823  0.337  -5.220 "C5'"  UPG 30 
UPG "C6'"  "C6'"  C 0 1 N N N 32.586 10.815 35.067 3.120  1.144  -5.143 "C6'"  UPG 31 
UPG "O2'"  "O2'"  O 0 1 N N N 29.878 13.546 39.180 -1.868 -1.151 -6.282 "O2'"  UPG 32 
UPG "O3'"  "O3'"  O 0 1 N N N 30.600 14.902 36.901 0.440  -2.000 -7.811 "O3'"  UPG 33 
UPG "O4'"  "O4'"  O 0 1 N N N 30.948 13.293 34.533 2.951  -1.368 -6.510 "O4'"  UPG 34 
UPG "O5'"  "O5'"  O 0 1 N N N 31.735 10.926 37.242 0.709  1.229  -5.222 "O5'"  UPG 35 
UPG "O6'"  "O6'"  O 0 1 N N N 32.414 9.376  35.139 3.127  1.922  -3.944 "O6'"  UPG 36 
UPG HN3    HN3    H 0 1 N N N 23.571 6.649  46.618 3.332  1.443  5.411  HN3    UPG 37 
UPG H5     H5     H 0 1 N N N 25.922 9.858  45.042 3.275  -2.109 7.593  H5     UPG 38 
UPG H6     H6     H 0 1 N N N 26.528 8.491  43.302 0.967  -2.447 6.878  H6     UPG 39 
UPG H1C    H1*    H 0 1 N N N 25.446 4.906  43.012 -0.876 -1.765 5.746  H1C    UPG 40 
UPG H2C    H2*    H 0 1 N N N 25.422 7.470  41.344 -0.789 1.298  5.568  H2C    UPG 41 
UPG HO2C   *HO2   H 0 0 N N N 23.973 6.134  40.206 -2.378 1.033  7.195  HO2C   UPG 42 
UPG H3C    H3*    H 0 1 N N N 26.798 6.341  39.618 -2.762 1.265  4.286  H3C    UPG 43 
UPG H4C    H4*    H 0 1 N N N 28.512 5.006  41.332 -2.487 -1.508 3.420  H4C    UPG 44 
UPG HO3C   *HO3   H 0 0 N N N 27.136 4.085  39.615 -3.922 0.193  5.977  HO3C   UPG 45 
UPG H5C1   1H5*   H 0 0 N N N 29.579 7.139  42.044 -1.361 1.107  2.309  H5C1   UPG 46 
UPG H5C2   2H5*   H 0 0 N N N 29.323 7.055  40.397 -2.978 0.449  1.961  H5C2   UPG 47 
UPG HOA2   2HOA   H 0 0 N N N 27.773 11.569 41.460 -3.472 -0.186 -0.615 HOA2   UPG 48 
UPG HOB2   2HOB   H 0 0 N N N 28.942 8.416  37.042 -2.965 -0.101 -3.132 HOB2   UPG 49 
UPG "H1'"  "H1'"  H 0 1 N N N 30.984 10.998 39.229 -1.334 1.097  -4.974 "H1'"  UPG 50 
UPG "H2'"  "H2'"  H 0 1 N N N 31.840 13.193 38.619 -0.730 0.278  -7.247 "H2'"  UPG 51 
UPG "H3'"  "H3'"  H 0 1 N N N 29.434 13.152 36.650 0.536  -2.061 -5.747 "H3'"  UPG 52 
UPG "H4'"  "H4'"  H 0 1 N N N 32.438 13.349 36.015 1.861  0.162  -7.370 "H4'"  UPG 53 
UPG "H5'"  "H5'"  H 0 1 N N N 30.461 11.071 35.540 1.755  -0.324 -4.357 "H5'"  UPG 54 
UPG "H6'1" "1H6'" H 0 0 N N N 32.620 11.211 34.025 3.188  1.806  -6.006 "H6'1" UPG 55 
UPG "H6'2" "2H6'" H 0 0 N N N 33.600 11.162 35.372 3.972  0.463  -5.139 "H6'2" UPG 56 
UPG "HO2'" "'HO2" H 0 0 N N N 29.905 14.495 39.213 -2.592 -0.520 -6.171 "HO2'" UPG 57 
UPG "HO3'" "'HO3" H 0 0 N N N 30.386 15.237 36.038 -0.388 -2.498 -7.802 "HO3'" UPG 58 
UPG "HO4'" "'HO4" H 0 0 N N N 31.539 12.953 33.871 2.905  -1.880 -7.329 "HO4'" UPG 59 
UPG "HO6'" "'HO6" H 0 0 N N N 33.117 9.012  34.613 3.959  2.414  -3.935 "HO6'" UPG 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 
UPG N1    C2     SING N N 1  
UPG N1    C6     SING N N 2  
UPG N1    C1C    SING N N 3  
UPG C2    N3     SING N N 4  
UPG C2    O2     DOUB N N 5  
UPG N3    C4     SING N N 6  
UPG N3    HN3    SING N N 7  
UPG C4    C5     SING N N 8  
UPG C4    O4     DOUB N N 9  
UPG C5    C6     DOUB N N 10 
UPG C5    H5     SING N N 11 
UPG C6    H6     SING N N 12 
UPG C1C   C2C    SING N N 13 
UPG C1C   O4C    SING N N 14 
UPG C1C   H1C    SING N N 15 
UPG C2C   O2C    SING N N 16 
UPG C2C   C3C    SING N N 17 
UPG C2C   H2C    SING N N 18 
UPG O2C   HO2C   SING N N 19 
UPG C3C   C4C    SING N N 20 
UPG C3C   O3C    SING N N 21 
UPG C3C   H3C    SING N N 22 
UPG C4C   O4C    SING N N 23 
UPG C4C   C5C    SING N N 24 
UPG C4C   H4C    SING N N 25 
UPG O3C   HO3C   SING N N 26 
UPG C5C   O5C    SING N N 27 
UPG C5C   H5C1   SING N N 28 
UPG C5C   H5C2   SING N N 29 
UPG O5C   PA     SING N N 30 
UPG PA    O1A    DOUB N N 31 
UPG PA    O2A    SING N N 32 
UPG PA    O3A    SING N N 33 
UPG O2A   HOA2   SING N N 34 
UPG O3A   PB     SING N N 35 
UPG PB    O1B    DOUB N N 36 
UPG PB    O2B    SING N N 37 
UPG PB    O3B    SING N N 38 
UPG O2B   HOB2   SING N N 39 
UPG O3B   "C1'"  SING N N 40 
UPG "C1'" "C2'"  SING N N 41 
UPG "C1'" "O5'"  SING N N 42 
UPG "C1'" "H1'"  SING N N 43 
UPG "C2'" "C3'"  SING N N 44 
UPG "C2'" "O2'"  SING N N 45 
UPG "C2'" "H2'"  SING N N 46 
UPG "C3'" "C4'"  SING N N 47 
UPG "C3'" "O3'"  SING N N 48 
UPG "C3'" "H3'"  SING N N 49 
UPG "C4'" "C5'"  SING N N 50 
UPG "C4'" "O4'"  SING N N 51 
UPG "C4'" "H4'"  SING N N 52 
UPG "C5'" "C6'"  SING N N 53 
UPG "C5'" "O5'"  SING N N 54 
UPG "C5'" "H5'"  SING N N 55 
UPG "C6'" "O6'"  SING N N 56 
UPG "C6'" "H6'1" SING N N 57 
UPG "C6'" "H6'2" SING N N 58 
UPG "O2'" "HO2'" SING N N 59 
UPG "O3'" "HO3'" SING N N 60 
UPG "O4'" "HO4'" SING N N 61 
UPG "O6'" "HO6'" SING N N 62 
# 
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 
UPG SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O)C1O)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=O)NC2=O)C(O)C3O 
UPG InChI            InChI                1.02b 
InChI=1/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1/f/h16,26,28H 
UPG InChIKey         InChI                1.02b HSCJRCZFDFQWRP-NNEFSTKSDV 
UPG SMILES_CANONICAL CACTVS               3.341 OC[C@H]1O[C@H](O[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)[C@H](O)[C@@H](O)[C@@H]1O 
UPG SMILES           CACTVS               3.341 OC[CH]1O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)[CH](O)[CH](O)[CH]1O 
UPG 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[P@](=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O 
UPG SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)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 
UPG "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,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" 
UPG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl] hydrogen phosphate" 
# 
