data_C5G
# 
_chem_comp.id                                    C5G 
_chem_comp.name                                  
;[CYTIDINE-5'-PHOSPHATE]-BETA-GLUCOSYL-PHOSPHORIC ACID ESTER
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H25 N3 O16 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-07-26 
_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                        565.317 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     C5G 
_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        1TZF 
_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 
C5G N1     N1     N 0 1 Y N N 21.935 3.120  28.642 -5.978 0.775  0.705  N1     C5G 1  
C5G C2     C2     C 0 1 Y N N 21.939 1.962  27.888 -5.765 1.504  -0.405 C2     C5G 2  
C5G N3     N3     N 0 1 Y N N 22.254 0.834  28.594 -6.350 2.689  -0.573 N3     C5G 3  
C5G C4     C4     C 0 1 Y N N 22.546 0.733  29.950 -7.161 3.181  0.355  C4     C5G 4  
C5G C5     C5     C 0 1 Y N N 22.504 1.983  30.638 -7.400 2.444  1.533  C5     C5G 5  
C5G C6     C6     C 0 1 Y N N 22.219 3.087  29.991 -6.802 1.239  1.686  C6     C5G 6  
C5G O2     O2     O 0 1 N N N 21.674 1.905  26.685 -5.023 1.073  -1.273 O2     C5G 7  
C5G N4     N4     N 0 1 N N N 22.796 -0.367 30.423 -7.759 4.406  0.171  N4     C5G 8  
C5G C1D    C1*    C 0 1 N N R 21.595 4.395  27.998 -5.320 -0.524 0.861  C1D    C5G 9  
C5G C2D    C2*    C 0 1 N N R 20.393 5.057  28.652 -5.801 -1.505 -0.231 C2D    C5G 10 
C5G O2D    O2*    O 0 1 N N N 19.152 4.638  28.077 -6.820 -2.369 0.276  O2D    C5G 11 
C5G C3D    C3*    C 0 1 N N S 20.601 6.571  28.417 -4.533 -2.316 -0.591 C3D    C5G 12 
C5G C4D    C4*    C 0 1 N N R 22.116 6.637  28.307 -3.439 -1.730 0.330  C4D    C5G 13 
C5G O4D    O4*    O 0 1 N N N 22.650 5.288  28.134 -3.897 -0.397 0.645  O4D    C5G 14 
C5G O3D    O3*    O 0 1 N N N 19.933 7.090  27.271 -4.730 -3.704 -0.314 O3D    C5G 15 
C5G C5D    C5*    C 0 1 N N N 22.775 7.227  29.509 -2.098 -1.672 -0.403 C5D    C5G 16 
C5G O5D    O5*    O 0 1 N N N 22.488 6.364  30.620 -1.093 -1.169 0.480  O5D    C5G 17 
C5G PA     PA     P 0 1 N N R 22.440 6.985  32.106 0.284  -1.136 -0.353 PA     C5G 18 
C5G O1A    O1A    O 0 1 N N N 21.816 8.332  32.204 0.558  -2.481 -0.907 O1A    C5G 19 
C5G O2A    O2A    O 0 1 N N N 21.912 6.091  33.151 0.158  -0.075 -1.556 O2A    C5G 20 
C5G O3A    O3A    O 0 1 N N N 24.058 7.120  32.326 1.490  -0.702 0.622  O3A    C5G 21 
C5G PB     PB     P 0 1 N N R 24.808 8.069  33.279 2.860  -1.069 -0.140 PB     C5G 22 
C5G O1B    O1B    O 0 1 N N N 24.786 7.568  34.689 2.772  -0.631 -1.551 O1B    C5G 23 
C5G O2B    O2B    O 0 1 N N N 24.074 9.389  33.235 3.094  -2.660 -0.086 O2B    C5G 24 
C5G "O1'"  "O1'"  O 0 1 N N N 26.354 8.221  32.764 4.091  -0.320 0.578  "O1'"  C5G 25 
C5G "C1'"  "C1'"  C 0 1 N N R 26.602 8.340  31.375 5.253  -0.587 -0.209 "C1'"  C5G 26 
C5G "C2'"  "C2'"  C 0 1 N N R 28.076 8.015  31.264 6.488  -0.599 0.694  "C2'"  C5G 27 
C5G "O2'"  "O2'"  O 0 1 N N N 28.271 6.732  31.887 6.354  -1.632 1.673  "O2'"  C5G 28 
C5G "C3'"  "C3'"  C 0 1 N N S 28.907 9.085  32.004 6.609  0.757  1.395  "C3'"  C5G 29 
C5G "O3'"  "O3'"  O 0 1 N N N 30.318 8.892  31.856 7.836  0.816  2.125  "O3'"  C5G 30 
C5G "C4'"  "C4'"  C 0 1 N N S 28.574 10.452 31.461 6.591  1.861  0.331  "C4'"  C5G 31 
C5G "O4'"  "O4'"  O 0 1 N N N 29.374 11.480 32.040 6.554  3.140  0.966  "O4'"  C5G 32 
C5G "C5'"  "C5'"  C 0 1 N N R 27.060 10.715 31.605 5.349  1.688  -0.546 "C5'"  C5G 33 
C5G "C6'"  "C6'"  C 0 1 N N N 26.672 12.007 30.919 5.305  2.805  -1.590 "C6'"  C5G 34 
C5G "O6'"  "O6'"  O 0 1 N N N 25.276 12.257 31.103 4.085  2.719  -2.330 "O6'"  C5G 35 
C5G "O5'"  "O5'"  O 0 1 N N N 26.282 9.692  30.935 5.394  0.424  -1.205 "O5'"  C5G 36 
C5G H5     H5     H 0 1 N N N 22.708 2.019  31.698 -8.058 2.831  2.297  H5     C5G 37 
C5G H6     H6     H 0 1 N N N 22.206 4.016  30.541 -6.974 0.654  2.577  H6     C5G 38 
C5G H41    1H4    H 0 1 N N N 23.016 -0.563 31.379 -7.589 4.912  -0.639 H41    C5G 39 
C5G H42    2H4    H 0 1 N N N 22.740 -1.035 29.681 -8.354 4.762  0.849  H42    C5G 40 
C5G H1D    H1*    H 0 1 N N N 21.377 4.166  26.944 -5.518 -0.933 1.852  H1D    C5G 41 
C5G H2D    H2*    H 0 1 N N N 20.331 4.786  29.716 -6.164 -0.958 -1.101 H2D    C5G 42 
C5G "HO'2" 2HO*   H 0 0 N N N 18.500 4.545  28.762 -7.034 -2.994 -0.430 "HO'2" C5G 43 
C5G H3D    H3*    H 0 1 N N N 20.170 7.198  29.212 -4.269 -2.170 -1.638 H3D    C5G 44 
C5G H4D    H4*    H 0 1 N N N 22.331 7.286  27.445 -3.349 -2.325 1.238  H4D    C5G 45 
C5G H3T    H3T    H 0 1 N N N 19.011 7.206  27.467 -5.421 -4.013 -0.916 H3T    C5G 46 
C5G "H5'1" 1H5*   H 0 0 N N N 22.399 8.243  29.699 -1.822 -2.673 -0.735 "H5'1" C5G 47 
C5G "H5'2" 2H5*   H 0 0 N N N 23.862 7.295  29.352 -2.184 -1.014 -1.268 "H5'2" C5G 48 
C5G HO2A   HO2A   H 0 0 N N N 21.798 5.218  32.794 -0.020 0.786  -1.153 HO2A   C5G 49 
C5G HO2B   HO2B   H 0 0 N N N 23.920 9.696  34.121 3.146  -2.904 0.848  HO2B   C5G 50 
C5G "H1'"  "H1'"  H 0 1 N N N 25.994 7.680  30.739 5.148  -1.559 -0.692 "H1'"  C5G 51 
C5G "H2'"  "H2'"  H 0 1 N N N 28.396 7.997  30.212 7.379  -0.780 0.093  "H2'"  C5G 52 
C5G HOD    "2HO'" H 0 1 N N N 28.314 6.058  31.219 6.281  -2.467 1.190  HOD    C5G 53 
C5G "H3'"  "H3'"  H 0 1 N N N 28.651 8.996  33.070 5.770  0.894  2.077  "H3'"  C5G 54 
C5G "HO'3" "3HO'" H 0 0 N N N 30.537 8.849  30.933 7.804  0.107  2.782  "HO'3" C5G 55 
C5G "H4'"  "H4'"  H 0 1 N N N 28.822 10.471 30.389 7.486  1.786  -0.287 "H4'"  C5G 56 
C5G "HO'4" "4HO'" H 0 0 N N N 29.552 11.269 32.949 7.353  3.207  1.507  "HO'4" C5G 57 
C5G "H5'"  "H5'"  H 0 1 N N N 26.859 10.739 32.686 4.456  1.740  0.077  "H5'"  C5G 58 
C5G "H6'1" "1H6'" H 0 0 N N N 26.886 11.924 29.843 5.360  3.772  -1.091 "H6'1" C5G 59 
C5G "H6'2" "2H6'" H 0 0 N N N 27.250 12.837 31.352 6.151  2.699  -2.271 "H6'2" C5G 60 
C5G "HO'6" "6HO'" H 0 0 N N N 25.083 12.312 32.032 4.098  3.439  -2.975 "HO'6" C5G 61 
# 
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 
C5G N1    C2     SING Y N 1  
C5G N1    C6     SING Y N 2  
C5G N1    C1D    SING N N 3  
C5G C2    N3     SING Y N 4  
C5G C2    O2     DOUB N N 5  
C5G N3    C4     DOUB Y N 6  
C5G C4    C5     SING Y N 7  
C5G C4    N4     SING N N 8  
C5G C5    C6     DOUB Y N 9  
C5G C5    H5     SING N N 10 
C5G C6    H6     SING N N 11 
C5G N4    H41    SING N N 12 
C5G N4    H42    SING N N 13 
C5G C1D   C2D    SING N N 14 
C5G C1D   O4D    SING N N 15 
C5G C1D   H1D    SING N N 16 
C5G C2D   O2D    SING N N 17 
C5G C2D   C3D    SING N N 18 
C5G C2D   H2D    SING N N 19 
C5G O2D   "HO'2" SING N N 20 
C5G C3D   C4D    SING N N 21 
C5G C3D   O3D    SING N N 22 
C5G C3D   H3D    SING N N 23 
C5G C4D   O4D    SING N N 24 
C5G C4D   C5D    SING N N 25 
C5G C4D   H4D    SING N N 26 
C5G O3D   H3T    SING N N 27 
C5G C5D   O5D    SING N N 28 
C5G C5D   "H5'1" SING N N 29 
C5G C5D   "H5'2" SING N N 30 
C5G O5D   PA     SING N N 31 
C5G PA    O1A    DOUB N N 32 
C5G PA    O2A    SING N N 33 
C5G PA    O3A    SING N N 34 
C5G O2A   HO2A   SING N N 35 
C5G O3A   PB     SING N N 36 
C5G PB    O1B    DOUB N N 37 
C5G PB    O2B    SING N N 38 
C5G PB    "O1'"  SING N N 39 
C5G O2B   HO2B   SING N N 40 
C5G "O1'" "C1'"  SING N N 41 
C5G "C1'" "C2'"  SING N N 42 
C5G "C1'" "O5'"  SING N N 43 
C5G "C1'" "H1'"  SING N N 44 
C5G "C2'" "O2'"  SING N N 45 
C5G "C2'" "C3'"  SING N N 46 
C5G "C2'" "H2'"  SING N N 47 
C5G "O2'" HOD    SING N N 48 
C5G "C3'" "O3'"  SING N N 49 
C5G "C3'" "C4'"  SING N N 50 
C5G "C3'" "H3'"  SING N N 51 
C5G "O3'" "HO'3" SING N N 52 
C5G "C4'" "O4'"  SING N N 53 
C5G "C4'" "C5'"  SING N N 54 
C5G "C4'" "H4'"  SING N N 55 
C5G "O4'" "HO'4" SING N N 56 
C5G "C5'" "C6'"  SING N N 57 
C5G "C5'" "O5'"  SING N N 58 
C5G "C5'" "H5'"  SING N N 59 
C5G "C6'" "O6'"  SING N N 60 
C5G "C6'" "H6'1" SING N N 61 
C5G "C6'" "H6'2" SING N N 62 
C5G "O6'" "HO'6" 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 
C5G SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O)C1O)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=NC2=O)N)C(O)C3O 
C5G InChI            InChI                1.02b 
InChI=1/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1/f/h26,28H,16H2 
C5G InChIKey         InChI                1.02b CGPHZDRCVSLMCF-HJJCBAQSDC 
C5G SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO[P@](O)(=O)O[P@@](O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O 
C5G SMILES           CACTVS               3.341 NC1=NC(=O)N(C=C1)[CH]2O[CH](CO[P](O)(=O)O[P](O)(=O)O[CH]3O[CH](CO)[CH](O)[CH](O)[CH]3O)[CH](O)[CH]2O 
C5G SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)[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 
C5G SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)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 
C5G "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-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)" 
C5G "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-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" 
# 
