data_LCH
# 
_chem_comp.id                                    LCH 
_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                     2004-09-16 
_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                     LCH 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye OEToolkits" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1W86 
_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 
LCH "O5'"  O5*  O 0 1 N N N -8.450  2.731  -4.562 -3.676 -1.812 1.181  "O5'"  LCH 1  
LCH "C5'"  C5*  C 0 1 N N N -8.244  2.297  -5.893 -2.824 -1.011 0.373  "C5'"  LCH 2  
LCH "C4'"  C4*  C 0 1 N N R -6.765  2.370  -6.271 -1.447 -1.627 0.340  "C4'"  LCH 3  
LCH "O4'"  O4*  O 0 1 N N N -6.240  3.699  -6.148 -0.885 -1.736 1.675  "O4'"  LCH 4  
LCH "C1'"  C1*  C 0 1 N N R -4.820  3.566  -6.253 0.244  -2.637 1.530  "C1'"  LCH 5  
LCH N1     N1   N 0 1 N N N -4.058  4.101  -5.079 0.097  -3.741 2.432  N1     LCH 6  
LCH C6     C6   C 0 1 N N N -4.662  4.364  -3.854 -1.037 -3.805 3.230  C6     LCH 7  
LCH C5     C5   C 0 1 N N N -3.953  4.768  -2.764 -1.270 -4.791 4.101  C5     LCH 8  
LCH C5M    C5M  C 0 1 N N N -4.643  5.019  -1.434 -2.486 -4.869 4.963  C5M    LCH 9  
LCH C4     C4   C 0 1 N N N -2.532  4.953  -2.927 -0.214 -5.851 4.172  C4     LCH 10 
LCH N4     N4   N 0 1 N N N -1.720  5.347  -1.936 -0.363 -6.909 5.042  N4     LCH 11 
LCH N3     N3   N 0 1 N N N -1.960  4.739  -4.161 0.859  -5.800 3.424  N3     LCH 12 
LCH C2     C2   C 0 1 N N N -2.681  4.295  -5.262 1.069  -4.766 2.532  C2     LCH 13 
LCH O2     O2   O 0 1 N N N -2.110  4.087  -6.332 2.088  -4.742 1.839  O2     LCH 14 
LCH "C3'"  C3*  C 0 1 N N S -5.769  1.544  -5.467 -1.321 -3.040 -0.189 "C3'"  LCH 15 
LCH "C2'"  C2*  C 0 1 N N R -4.670  2.055  -6.411 0.175  -3.027 0.054  "C2'"  LCH 16 
LCH "O2'"  O2*  O 0 1 N N N -5.073  1.851  -7.747 0.630  -1.857 -0.678 "O2'"  LCH 17 
LCH "O3'"  O3*  O 0 1 N N N -5.958  0.154  -5.137 -1.643 -3.192 -1.554 "O3'"  LCH 18 
LCH "C6'"  C6*  C 0 1 N N N -6.475  1.912  -7.700 -0.422 -0.873 -0.507 "C6'"  LCH 19 
LCH P      P    P 0 1 N N N -9.898  3.264  -4.086 -5.214 -1.349 1.368  P      LCH 20 
LCH O1P    O1P  O 0 1 N N N -10.945 2.471  -4.769 -6.047 -2.248 2.235  O1P    LCH 21 
LCH O2P    O2P  O 0 1 N N N -9.894  3.368  -2.609 -5.067 0.170  1.901  O2P    LCH 22 
LCH OXT    OXT  O 0 1 N Y N -9.901  4.757  -4.721 -5.747 -1.162 -0.147 OXT    LCH 23 
LCH "H5'1" 1H5* H 0 0 N N N -8.802  2.941  -6.576 -3.250 -0.956 -0.636 "H5'1" LCH 24 
LCH "H5'2" 2H5* H 0 0 N N N -8.606  1.274  -6.000 -2.789 -0.001 0.798  "H5'2" LCH 25 
LCH "H1'"  H1*  H 0 1 N N N -4.455  3.989  -7.195 1.158  -2.092 1.788  "H1'"  LCH 26 
LCH H6     H6   H 0 1 N N N -5.733  4.257  -3.732 -1.739 -2.988 3.100  H6     LCH 27 
LCH H5M1   1H5M H 0 0 N N N -4.305  5.965  -1.012 -2.203 -4.776 6.012  H5M1   LCH 28 
LCH H5M2   2H5M H 0 0 N N N -4.402  4.210  -0.743 -2.988 -5.824 4.810  H5M2   LCH 29 
LCH H5M3   3H5M H 0 0 N N N -5.724  5.063  -1.566 -3.175 -4.064 4.705  H5M3   LCH 30 
LCH H41    1H4  H 0 1 N N N -0.730  5.482  -2.106 -1.283 -7.204 5.260  H41    LCH 31 
LCH H42    2H4  H 0 1 N N N -2.085  5.504  -1.007 0.457  -7.327 5.408  H42    LCH 32 
LCH "H3'"  H3*  H 0 1 N N N -5.659  2.018  -4.491 -1.845 -3.795 0.407  "H3'"  LCH 33 
LCH "H2'1" 1H2* H 0 0 N N N -3.655  1.719  -6.252 0.739  -3.910 -0.252 "H2'1" LCH 34 
LCH HA     HA   H 0 1 N N N -5.337  -0.361 -4.636 -0.902 -3.661 -1.977 HA     LCH 35 
LCH "H6'1" 1H6* H 0 0 N N N -6.888  2.586  -8.451 -0.793 -0.593 -1.497 "H6'1" LCH 36 
LCH "H6'2" 2H6* H 0 0 N N N -6.803  0.899  -7.829 0.000  -0.000 -0.000 "H6'2" LCH 37 
LCH HXT    HXT  H 0 1 N Y N -0.851  0.313  0.280  -6.692 -0.943 -0.294 HXT    LCH 38 
LCH HO1    HO1  H 0 1 N N N -9.893  2.497  -2.230 -5.873 0.654  2.183  HO1    LCH 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 
LCH "O5'" "C5'"  SING N N 1  
LCH "O5'" P      SING N N 2  
LCH "C5'" "C4'"  SING N N 3  
LCH "C5'" "H5'1" SING N N 4  
LCH "C5'" "H5'2" SING N N 5  
LCH "C4'" "O4'"  SING N N 6  
LCH "C4'" "C3'"  SING N N 7  
LCH "C4'" "C6'"  SING N N 8  
LCH "O4'" "C1'"  SING N N 9  
LCH "C1'" N1     SING N N 10 
LCH "C1'" "C2'"  SING N N 11 
LCH "C1'" "H1'"  SING N N 12 
LCH N1    C6     SING N N 13 
LCH N1    C2     SING N N 14 
LCH C6    C5     DOUB N N 15 
LCH C6    H6     SING N N 16 
LCH C5    C5M    SING N N 17 
LCH C5    C4     SING N N 18 
LCH C5M   H5M1   SING N N 19 
LCH C5M   H5M2   SING N N 20 
LCH C5M   H5M3   SING N N 21 
LCH C4    N4     SING N N 22 
LCH C4    N3     DOUB N N 23 
LCH N4    H41    SING N N 24 
LCH N4    H42    SING N N 25 
LCH N3    C2     SING N N 26 
LCH C2    O2     DOUB N N 27 
LCH "C3'" "C2'"  SING N N 28 
LCH "C3'" "O3'"  SING N N 29 
LCH "C3'" "H3'"  SING N N 30 
LCH "C2'" "O2'"  SING N N 31 
LCH "C2'" "H2'1" SING N N 32 
LCH "O2'" "C6'"  SING N N 33 
LCH "O3'" HA     SING N N 34 
LCH "C6'" "H6'1" SING N N 35 
LCH "C6'" "H6'2" SING N N 36 
LCH P     O1P    DOUB N N 37 
LCH P     O2P    SING N N 38 
LCH P     OXT    SING N N 39 
LCH OXT   HXT    SING N N 40 
LCH HO1   O2P    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 
LCH SMILES           ACDLabs              10.04 "O=C1N=C(N)C(=CN1C3OC2(C(O)C3OC2)COP(=O)(O)O)C"                                                                                                                               
LCH 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" 
LCH InChIKey         InChI                1.02b RSSHBVFUGGVGMZ-MGOZBQMSDB                                                                                                                                                     
LCH 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"                                                                                                             
LCH SMILES           CACTVS               3.341 "CC1=CN([CH]2O[C]3(CO[CH]2[CH]3O)CO[P](O)(O)=O)C(=O)N=C1N"                                                                                                                    
LCH 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"                                                                                                            
LCH 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 
LCH "SYSTEMATIC NAME" ACDLabs              10.04 "4-amino-1-{2,5-anhydro-4-[(phosphonooxy)methyl]-alpha-L-lyxofuranosyl}-5-methylpyrimidin-2(1H)-one"                                
LCH "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" 
# 
