data_RCE
# 
_chem_comp.id                                    RCE 
_chem_comp.name                                  "1-{2,5-anhydro-6-deoxy-4-[(phosphonooxy)methyl]-beta-D-gulofuranosyl}pyrimidine-2,4(1H,3H)-dione" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H15 N2 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-01-11 
_chem_comp.pdbx_modified_date                    2012-06-15 
_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                        350.219 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RCE 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3UKB 
_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 
RCE P      P      P 0 1 N N N 3.721  -9.320  6.535 -4.224 -1.035 0.164  P      RCE 1  
RCE N1     N1     N 0 1 N N N -0.563 -6.318  4.714 2.534  -0.116 0.340  N1     RCE 2  
RCE C2     C2     C 0 1 N N N -1.534 -5.388  4.509 3.778  0.230  0.720  C2     RCE 3  
RCE O2     O2     O 0 1 N N N -2.302 -5.479  3.441 3.956  1.282  1.302  O2     RCE 4  
RCE N3     N3     N 0 1 N N N -1.749 -4.430  5.371 4.827  -0.574 0.465  N3     RCE 5  
RCE C4     C4     C 0 1 N N N -0.957 -4.220  6.452 4.646  -1.744 -0.179 C4     RCE 6  
RCE O4     O4     O 0 1 N N N -1.160 -3.256  7.195 5.595  -2.472 -0.409 O4     RCE 7  
RCE C5     C5     C 0 1 N N N 0.125  -5.145  6.691 3.343  -2.120 -0.585 C5     RCE 8  
RCE C6     C6     C 0 1 N N N 0.244  -6.222  5.818 2.308  -1.295 -0.317 C6     RCE 9  
RCE "C1'"  "C1'"  C 0 1 N N R -0.470 -7.448  3.766 1.411  0.776  0.637  "C1'"  RCE 10 
RCE O1P    O1P    O 0 1 N N N 4.709  -10.391 6.084 -3.994 -2.398 -0.364 O1P    RCE 11 
RCE "C2'"  "C2'"  C 0 1 N N R 0.381  -7.108  2.545 1.266  1.855  -0.482 "C2'"  RCE 12 
RCE O2A    O2A    O 0 1 N N N 0.191  -8.263  1.699 0.309  2.803  0.070  O2A    RCE 13 
RCE O2P    O2P    O 0 1 N N N 4.339  -8.166  7.315 -5.199 -0.231 -0.833 O2P    RCE 14 
RCE "C3'"  "C3'"  C 0 1 N N S 1.777  -7.352  3.084 0.358  1.053  -1.483 "C3'"  RCE 15 
RCE "O3'"  "O3'"  O 0 1 N N N 2.794  -7.374  2.066 -0.201 1.884  -2.503 "O3'"  RCE 16 
RCE O3P    O3P    O 0 1 N Y N 2.532  -10.077 7.360 -4.905 -1.131 1.620  O3P    RCE 17 
RCE "C4'"  "C4'"  C 0 1 N N R 1.429  -8.736  3.554 -0.687 0.678  -0.371 "C4'"  RCE 18 
RCE "O4'"  "O4'"  O 0 1 N N N 0.272  -8.510  4.389 0.171  0.041  0.619  "O4'"  RCE 19 
RCE "C5'"  "C5'"  C 0 1 N N N 2.519  -9.498  4.270 -1.922 -0.104 -0.823 "C5'"  RCE 20 
RCE "O5'"  "O5'"  O 0 1 N N N 3.007  -8.701  5.303 -2.817 -0.260 0.279  "O5'"  RCE 21 
RCE "C6'"  "C6'"  C 0 1 N N R 0.964  -9.377  2.264 -0.941 2.101  0.217  "C6'"  RCE 22 
RCE "C7'"  "C7'"  C 0 1 N N N 0.113  -10.629 2.462 -1.324 2.004  1.695  "C7'"  RCE 23 
RCE H5     H5     H 0 1 N N N 0.813  -5.007  7.512 3.179  -3.053 -1.102 H5     RCE 24 
RCE H6     H6     H 0 1 N N N 0.979  -6.989  6.012 1.307  -1.565 -0.618 H6     RCE 25 
RCE "H1'"  "H1'"  H 0 1 N N N -1.470 -7.782  3.453 1.554  1.253  1.606  "H1'"  RCE 26 
RCE "H2'"  "H2'"  H 0 1 N N N 0.203  -6.119  2.098 2.193  2.265  -0.884 "H2'"  RCE 27 
RCE HO2P   HO2P   H 0 0 N N N 5.275  -8.305  7.398 -5.394 0.673  -0.549 HO2P   RCE 28 
RCE "H3'"  "H3'"  H 0 1 N N N 2.017  -6.679  3.920 0.862  0.178  -1.896 "H3'"  RCE 29 
RCE "HO3'" "HO3'" H 0 0 N Y N 3.641  -7.530  2.467 0.458  2.311  -3.067 "HO3'" RCE 30 
RCE HO3P   HO3P   H 0 0 N Y N 2.707  -11.011 7.383 -5.757 -1.587 1.626  HO3P   RCE 31 
RCE "H5'"  "H5'"  H 0 1 N N N 2.110  -10.432 4.683 -2.423 0.441  -1.624 "H5'"  RCE 32 
RCE "H5'A" "H5'A" H 0 0 N N N 3.331  -9.733  3.567 -1.618 -1.085 -1.186 "H5'A" RCE 33 
RCE "H6'"  "H6'"  H 0 1 N N N 1.829  -9.611  1.627 -1.727 2.607  -0.345 "H6'"  RCE 34 
RCE "H7'"  "H7'"  H 0 1 N N N 0.734  -11.432 2.886 -1.453 3.006  2.104  "H7'"  RCE 35 
RCE "H7'A" "H7'A" H 0 0 N N N -0.715 -10.404 3.150 -2.257 1.449  1.793  "H7'A" RCE 36 
RCE "H7'B" "H7'B" H 0 0 N N N -0.294 -10.953 1.493 -0.535 1.487  2.241  "H7'B" RCE 37 
RCE HN3    HN3    H 0 1 N N N -2.532 -3.825  5.227 5.717  -0.310 0.747  HN3    RCE 38 
# 
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 
RCE "O5'" P      SING N N 1  
RCE O1P   P      DOUB N N 2  
RCE P     O2P    SING N N 3  
RCE P     O3P    SING N N 4  
RCE "C1'" N1     SING N N 5  
RCE C2    N1     SING N N 6  
RCE N1    C6     SING N N 7  
RCE O2    C2     DOUB N N 8  
RCE C2    N3     SING N N 9  
RCE N3    C4     SING N N 10 
RCE C4    C5     SING N N 11 
RCE C4    O4     DOUB N N 12 
RCE C6    C5     DOUB N N 13 
RCE C5    H5     SING N N 14 
RCE C6    H6     SING N N 15 
RCE "C2'" "C1'"  SING N N 16 
RCE "C1'" "O4'"  SING N N 17 
RCE "C1'" "H1'"  SING N N 18 
RCE O2A   "C2'"  SING N N 19 
RCE "C2'" "C3'"  SING N N 20 
RCE "C2'" "H2'"  SING N N 21 
RCE O2A   "C6'"  SING N N 22 
RCE O2P   HO2P   SING N N 23 
RCE "O3'" "C3'"  SING N N 24 
RCE "C3'" "C4'"  SING N N 25 
RCE "C3'" "H3'"  SING N N 26 
RCE "O3'" "HO3'" SING N N 27 
RCE O3P   HO3P   SING N N 28 
RCE "C6'" "C4'"  SING N N 29 
RCE "C4'" "C5'"  SING N N 30 
RCE "C4'" "O4'"  SING N N 31 
RCE "C5'" "O5'"  SING N N 32 
RCE "C5'" "H5'"  SING N N 33 
RCE "C5'" "H5'A" SING N N 34 
RCE "C6'" "C7'"  SING N N 35 
RCE "C6'" "H6'"  SING N N 36 
RCE "C7'" "H7'"  SING N N 37 
RCE "C7'" "H7'A" SING N N 38 
RCE "C7'" "H7'B" SING N N 39 
RCE N3    HN3    SING N N 40 
# 
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 
RCE SMILES           ACDLabs              12.01 "O=P(O)(O)OCC32OC(N1C(=O)NC(=O)C=C1)C(OC2C)C3O"                                                                                                                     
RCE InChI            InChI                1.03  "InChI=1S/C11H15N2O9P/c1-5-11(4-20-23(17,18)19)8(15)7(21-5)9(22-11)13-3-2-6(14)12-10(13)16/h2-3,5,7-9,15H,4H2,1H3,(H,12,14,16)(H2,17,18,19)/t5-,7-,8+,9-,11+/m1/s1" 
RCE InChIKey         InChI                1.03  YMFXFISZLBZENQ-QPLYKKBVSA-N                                                                                                                                         
RCE SMILES_CANONICAL CACTVS               3.370 "C[C@H]1O[C@@H]2[C@H](O)[C@@]1(CO[P](O)(O)=O)O[C@H]2N3C=CC(=O)NC3=O"                                                                                                
RCE SMILES           CACTVS               3.370 "C[CH]1O[CH]2[CH](O)[C]1(CO[P](O)(O)=O)O[CH]2N3C=CC(=O)NC3=O"                                                                                                       
RCE SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@@H]1[C@]2([C@H]([C@@H](O1)[C@@H](O2)N3C=CC(=O)NC3=O)O)COP(=O)(O)O"                                                                                             
RCE SMILES           "OpenEye OEToolkits" 1.7.6 "CC1C2(C(C(O1)C(O2)N3C=CC(=O)NC3=O)O)COP(=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 
RCE "SYSTEMATIC NAME" ACDLabs              12.01 "1-{2,5-anhydro-6-deoxy-4-[(phosphonooxy)methyl]-beta-D-gulofuranosyl}pyrimidine-2,4(1H,3H)-dione"                                              
RCE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(1R,3R,4R,6R,7S)-6-[2,4-bis(oxidanylidene)pyrimidin-1-yl]-3-methyl-7-oxidanyl-2,5-dioxabicyclo[2.2.1]heptan-4-yl]methyl dihydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
RCE "Create component" 2012-01-11 RCSB 
# 
