data_LCC
# 
_chem_comp.id                                    LCC 
_chem_comp.name                                  "[(1R,3R,4R,7S)-7-HYDROXY-3-(5-METHYLCYTOSIN-1-YL)-2,5-DIOXABICYCLO[2.2.1]HEPT-1-YL]METHYL DIHYDROGEN PHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H16 N3 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-06-27 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        349.234 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     LCC 
_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        1H0Q 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
LCC "O5'"  O5*  O 0 1 N N N -1.824 13.118 -12.576 0.106  -0.679 -2.962 "O5'"  LCC 1  
LCC "C5'"  C5*  C 0 1 N N N -2.609 12.840 -13.720 -0.069 0.496  -2.169 "C5'"  LCC 2  
LCC "C4'"  C4*  C 0 1 N N R -3.999 12.416 -13.240 -0.910 0.159  -0.936 "C4'"  LCC 3  
LCC "O4'"  O4*  O 0 1 N N N -3.969 11.205 -12.475 -0.352 -0.832 -0.027 "O4'"  LCC 4  
LCC "C1'"  C1*  C 0 1 N N R -5.142 11.212 -11.663 -1.113 -0.757 1.194  "C1'"  LCC 5  
LCC N1     N1   N 0 1 N N N -4.841 11.305 -10.199 -0.229 -0.471 2.326  N1     LCC 6  
LCC C6     C6   C 0 1 N N N -3.606 11.710 -9.736  0.987  0.102  2.108  C6     LCC 7  
LCC C5     C5   C 0 1 N N N -3.341 11.801 -8.408  1.796  0.362  3.162  C5     LCC 8  
LCC C5M    C5M  C 0 1 N N N -1.979 12.266 -7.921  3.147  0.995  2.952  C5M    LCC 9  
LCC C4     C4   C 0 1 N N N -4.402 11.439 -7.497  1.357  0.024  4.459  C4     LCC 10 
LCC N4     N4   N 0 1 N N N -4.235 11.486 -6.171  2.159  0.277  5.548  N4     LCC 11 
LCC N3     N3   N 0 1 N N N -5.595 11.035 -7.956  0.162  -0.527 4.624  N3     LCC 12 
LCC C2     C2   C 0 1 N N N -5.852 10.954 -9.293  -0.621 -0.776 3.577  C2     LCC 13 
LCC O2     O2   O 0 1 N N N -6.958 10.583 -9.683  -1.713 -1.290 3.754  O2     LCC 14 
LCC "C3'"  C3*  C 0 1 N N S -4.699 13.430 -12.335 -1.238 1.332  0.056  "C3'"  LCC 15 
LCC "C2'"  C2*  C 0 1 N N R -5.861 12.456 -12.210 -2.120 0.416  0.984  "C2'"  LCC 16 
LCC "O2'"  O2*  O 0 1 N N N -6.259 12.171 -13.555 -3.078 -0.113 0.025  "O2'"  LCC 17 
LCC "O3'"  O3*  O 0 1 N N N -5.042 14.680 -12.912 -1.993 2.378  -0.558 "O3'"  LCC 18 
LCC "C6'"  C6*  C 0 1 N N N -5.064 12.243 -14.333 -2.360 -0.350 -1.201 "C6'"  LCC 19 
LCC P      P    P 0 1 N N N -0.315 13.673 -12.669 0.994  -0.254 -4.236 P      LCC 20 
LCC O1P    O1P  O 0 1 N N N -0.274 14.726 -13.709 1.232  -1.538 -5.177 O1P    LCC 21 
LCC O2P    O2P  O 0 1 N N N 0.128  13.987 -11.293 2.299  0.268  -3.774 O2P    LCC 22 
LCC OXT    OXT  O 0 1 N Y N 0.540  12.411 -13.197 0.223  0.886  -5.070 OXT    LCC 23 
LCC "H5'1" 1H5* H 0 0 N N N -2.157 12.039 -14.305 0.904  0.871  -1.854 "H5'1" LCC 24 
LCC "H5'2" 2H5* H 0 0 N N N -2.692 13.736 -14.337 -0.579 1.258  -2.759 "H5'2" LCC 25 
LCC "H1'"  H1*  H 0 1 N N N -5.755 10.320 -11.823 -1.651 -1.690 1.362  "H1'"  LCC 26 
LCC H6     H6   H 0 1 N N N -2.836 11.973 -10.443 1.302  0.348  1.104  H6     LCC 27 
LCC H5M1   1H5M H 0 0 N N N -1.601 11.580 -7.162  3.643  1.122  3.915  H5M1   LCC 28 
LCC H5M2   2H5M H 0 0 N N N -1.268 12.293 -8.748  3.754  0.354  2.313  H5M2   LCC 29 
LCC H5M3   3H5M H 0 0 N N N -2.066 13.264 -7.494  3.022  1.968  2.477  H5M3   LCC 30 
LCC H41    1H4  H 0 1 N N N -4.998 11.204 -5.568  1.851  0.051  6.439  H41    LCC 31 
LCC H42    2H4  H 0 1 N N N -3.347 11.763 -5.782  3.032  0.681  5.424  H42    LCC 32 
LCC "H3'"  H3*  H 0 1 N N N -4.169 13.582 -11.395 -0.351 1.711  0.564  "H3'"  LCC 33 
LCC "H2'1" 1H2* H 0 0 N N N -6.668 12.804 -11.568 -2.537 0.881  1.878  "H2'1" LCC 34 
LCC H3T    H3T  H 0 1 N Y N -4.236 15.185 -13.043 -2.347 2.925  0.156  H3T    LCC 35 
LCC "H6'1" 1H6* H 0 0 N N N -4.893 11.360 -14.953 -2.814 0.209  -2.019 "H6'1" LCC 36 
LCC "H6'2" 2H6* H 0 0 N N N -5.096 13.127 -14.972 -2.350 -1.416 -1.433 "H6'2" LCC 37 
LCC H1P    H1P  H 0 1 N N N 0.616  15.053 -13.764 1.767  -1.241 -5.925 H1P    LCC 38 
LCC HXT    HXT  H 0 1 N N N 1.430  12.738 -13.252 -0.619 0.505  -5.351 HXT    LCC 39 
# 
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 
LCC "O5'" "C5'"  SING N N 1  
LCC "O5'" P      SING N N 2  
LCC "C5'" "C4'"  SING N N 3  
LCC "C5'" "H5'1" SING N N 4  
LCC "C5'" "H5'2" SING N N 5  
LCC "C4'" "O4'"  SING N N 6  
LCC "C4'" "C3'"  SING N N 7  
LCC "C4'" "C6'"  SING N N 8  
LCC "O4'" "C1'"  SING N N 9  
LCC "C1'" N1     SING N N 10 
LCC "C1'" "C2'"  SING N N 11 
LCC "C1'" "H1'"  SING N N 12 
LCC N1    C6     SING N N 13 
LCC N1    C2     SING N N 14 
LCC C6    C5     DOUB N N 15 
LCC C6    H6     SING N N 16 
LCC C5    C5M    SING N N 17 
LCC C5    C4     SING N N 18 
LCC C5M   H5M1   SING N N 19 
LCC C5M   H5M2   SING N N 20 
LCC C5M   H5M3   SING N N 21 
LCC C4    N4     SING N N 22 
LCC C4    N3     DOUB N N 23 
LCC N4    H41    SING N N 24 
LCC N4    H42    SING N N 25 
LCC N3    C2     SING N N 26 
LCC C2    O2     DOUB N N 27 
LCC "C3'" "C2'"  SING N N 28 
LCC "C3'" "O3'"  SING N N 29 
LCC "C3'" "H3'"  SING N N 30 
LCC "C2'" "O2'"  SING N N 31 
LCC "C2'" "H2'1" SING N N 32 
LCC "O2'" "C6'"  SING N N 33 
LCC "O3'" H3T    SING N N 34 
LCC "C6'" "H6'1" SING N N 35 
LCC "C6'" "H6'2" SING N N 36 
LCC P     O1P    SING N N 37 
LCC P     O2P    DOUB N N 38 
LCC P     OXT    SING N N 39 
LCC O1P   H1P    SING N N 40 
LCC OXT   HXT    SING N N 41 
# 
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 
LCC SMILES           ACDLabs              10.04 "O=C1N=C(N)C(=CN1C3OC2(C(O)C3OC2)COP(=O)(O)O)C"                                                                                                                               
LCC InChI            InChI                1.02b "InChI=1/C11H16N3O8P/c1-5-2-14(10(16)13-8(5)12)9-6-7(15)11(22-9,3-20-6)4-21-23(17,18)19/h2,6-7,9,15H,3-4H2,1H3,(H2,12,13,16)(H2,17,18,19)/t6-,7+,9-,11-/m1/s1/f/h17-18H,12H2" 
LCC InChIKey         InChI                1.02b RSSHBVFUGGVGMZ-MGOZBQMSDB                                                                                                                                                     
LCC SMILES_CANONICAL CACTVS               3.341 "CC1=CN([C@@H]2O[C@]3(CO[C@@H]2[C@@H]3O)CO[P](O)(O)=O)C(=O)N=C1N"                                                                                                             
LCC SMILES           CACTVS               3.341 "CC1=CN([CH]2O[C]3(CO[CH]2[CH]3O)CO[P](O)(O)=O)C(=O)N=C1N"                                                                                                                    
LCC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)N=C1N)[C@H]2[C@H]3[C@@H]([C@@](O2)(CO3)COP(=O)(O)O)O"                                                                                                            
LCC SMILES           "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)N=C1N)C2C3C(C(O2)(CO3)COP(=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 
LCC "SYSTEMATIC NAME" ACDLabs              10.04 "4-amino-1-{2,5-anhydro-4-[(phosphonooxy)methyl]-alpha-L-lyxofuranosyl}-5-methylpyrimidin-2(1H)-one"                                
LCC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R,4R,5R,7S)-5-(4-amino-5-methyl-2-oxo-pyrimidin-1-yl)-7-hydroxy-3,6-dioxabicyclo[2.2.1]heptan-1-yl]methyl dihydrogen phosphate" 
# 
