data_F3H
#

_chem_comp.id                                   F3H
_chem_comp.name                                 "1,5-anhydro-2,3-dideoxy-3-fluoro-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-O-phosphono-D-altritol"
_chem_comp.type                                 "DNA linking"
_chem_comp.pdbx_type                            ATOMN
_chem_comp.formula                              "C11 H16 F N2 O8 P"
_chem_comp.mon_nstd_parent_comp_id              DT
_chem_comp.pdbx_synonyms                        "1,5-anhydro-2,3-dideoxy-3-fluoro-2-(thymin-1-yl)-D-altritol-5-dihydrogenphosphate"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2011-01-04
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       354.226
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    F3H
_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       3Q61
_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
F3H  P       P       P  0  1  N  N  N  10.585  4.743  3.051   4.327  -0.743   0.111  P       F3H   1  
F3H  N1      N1      N  0  1  N  N  N   5.685  6.682  5.290  -2.475   0.210  -0.536  N1      F3H   2  
F3H  C2      C2      C  0  1  N  N  N   4.803  6.882  6.346  -3.572   0.304   0.238  C2      F3H   3  
F3H  O2      O2      O  0  1  N  N  N   3.947  7.880  6.379  -4.043   1.398   0.480  O2      F3H   4  
F3H  N3      N3      N  0  1  N  N  N   4.827  6.036  7.391  -4.154  -0.797   0.749  N3      F3H   5  
F3H  C4      C4      C  0  1  N  N  N   5.716  5.006  7.427  -3.644  -2.018   0.490  C4      F3H   6  
F3H  O4      O4      O  0  1  N  N  N   5.688  4.239  8.481  -4.171  -3.014   0.951  O4      F3H   7  
F3H  C5      C5      C  0  1  N  N  N   6.655  4.805  6.394  -2.490  -2.131  -0.322  C5      F3H   8  
F3H  C6      C6      C  0  1  N  N  N   6.587  5.664  5.310  -1.926  -1.010  -0.822  C6      F3H   9  
F3H  "C1'"   "C1'"   C  0  1  N  N  R   5.647  7.674  4.212  -1.867   1.426  -1.082  "C1'"   F3H  10  
F3H  "C2'"   "C2'"   C  0  1  N  N  S   6.726  8.726  4.400  -1.350   2.300   0.065  "C2'"   F3H  11  
F3H  "F2'"   "F2'"   F  0  1  N  N  N   6.417  9.736  3.538  -0.828   3.490  -0.453  "F2'"   F3H  12  
F3H  "C3'"   "C3'"   C  0  1  N  N  R   8.107  8.183  4.019  -0.252   1.541   0.816  "C3'"   F3H  13  
F3H  "O3'"   "O3'"   O  0  1  N  N  N   9.041  9.277  4.031   0.288   2.375   1.843  "O3'"   F3H  14  
F3H  "C4'"   "C4'"   C  0  1  N  N  R   8.056  7.568  2.608   0.857   1.157  -0.168  "C4'"   F3H  15  
F3H  "O4'"   "O4'"   O  0  1  N  N  N   7.009  6.588  2.610   0.303   0.371  -1.225  "O4'"   F3H  16  
F3H  "C5'"   "C5'"   C  0  1  N  N  N   9.364  6.865  2.312   1.929   0.346   0.563  "C5'"   F3H  17  
F3H  "O5'"   "O5'"   O  0  1  N  N  N   9.588  5.921  3.328   3.019   0.088  -0.324  "O5'"   F3H  18  
F3H  C5M     C5M     C  0  1  N  N  N   7.674  3.701  6.487  -1.900  -3.483  -0.626  C5M     F3H  19  
F3H  "C6'"   "C6'"   C  0  1  N  N  N   5.714  7.103  2.812  -0.696   1.047  -1.992  "C6'"   F3H  20  
F3H  OP1     OP1     O  0  1  N  N  N  11.899  5.361  2.354   5.281  -0.951  -1.168  OP1     F3H  21  
F3H  OP2     OP2     O  0  1  N  N  N  10.841  3.961  4.415   5.124   0.070   1.250  OP2     F3H  22  
F3H  OP3     OP3     O  0  1  N  N  N   9.933  3.795  1.989   3.918  -2.063   0.642  OP3     F3H  23  
F3H  HN3     HN3     H  0  1  N  N  N   4.186  6.165  8.148  -4.944  -0.711   1.305  HN3     F3H  24  
F3H  H6      H6      H  0  1  N  N  N   7.256  5.525  4.473  -1.046  -1.077  -1.444  H6      F3H  25  
F3H  "H1'"   "H1'"   H  0  1  N  N  N   4.652  8.135  4.296  -2.611   1.979  -1.656  "H1'"   F3H  26  
F3H  "H2'"   "H2'"   H  0  1  N  N  N   6.763  9.047  5.452  -2.169   2.527   0.747  "H2'"   F3H  27  
F3H  "H3'"   "H3'"   H  0  1  N  N  N   8.416  7.407  4.734  -0.673   0.639   1.262  "H3'"   F3H  28  
F3H  "HO3'"  "HO3'"  H  0  0  N  N  N   9.905  8.959  3.797  -0.362   2.660   2.500  "HO3'"  F3H  29  
F3H  "H4'"   "H4'"   H  0  1  N  N  N   7.882  8.350  1.854   1.304   2.061  -0.582  "H4'"   F3H  30  
F3H  "H5'"   "H5'"   H  0  1  N  N  N   9.307  6.361  1.336   2.287   0.911   1.424  "H5'"   F3H  31  
F3H  "H5'A"  "H5'A"  H  0  0  N  N  N  10.186  7.595  2.289   1.503  -0.599   0.900  "H5'A"  F3H  32  
F3H  H5M     H5M     H  0  1  N  N  N   8.309  3.711  5.589  -2.492  -4.257  -0.137  H5M     F3H  33  
F3H  H5MA    H5MA    H  0  0  N  N  N   8.299  3.853  7.379  -1.905  -3.649  -1.704  H5MA    F3H  34  
F3H  H5MB    H5MB    H  0  0  N  N  N   7.159  2.732  6.561  -0.875  -3.523  -0.258  H5MB    F3H  35  
F3H  "H6'"   "H6'"   H  0  1  N  N  N   4.970  6.301  2.698  -1.050   0.389  -2.786  "H6'"   F3H  36  
F3H  "H6'A"  "H6'A"  H  0  0  N  N  N   5.506  7.892  2.075  -0.269   1.949  -2.431  "H6'A"  F3H  37  
F3H  HOP1    HOP1    H  0  0  N  N  N  11.981  5.018  1.472   6.091  -1.445  -0.979  HOP1    F3H  38  
F3H  HOP2    HOP2    H  0  0  N  N  N  10.548  3.062  4.325   5.423   0.946   0.971  HOP2    F3H  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
F3H  OP3    P       DOUB  N  N   1  
F3H  OP1    P       SING  N  N   2  
F3H  P      "O5'"   SING  N  N   3  
F3H  P      OP2     SING  N  N   4  
F3H  "C1'"  N1      SING  N  N   5  
F3H  N1     C6      SING  N  N   6  
F3H  N1     C2      SING  N  N   7  
F3H  C2     O2      DOUB  N  N   8  
F3H  C2     N3      SING  N  N   9  
F3H  N3     C4      SING  N  N  10  
F3H  N3     HN3     SING  N  N  11  
F3H  C5     C4      SING  N  N  12  
F3H  C4     O4      DOUB  N  N  13  
F3H  C6     C5      DOUB  N  N  14  
F3H  C5     C5M     SING  N  N  15  
F3H  C6     H6      SING  N  N  16  
F3H  "C6'"  "C1'"   SING  N  N  17  
F3H  "C1'"  "C2'"   SING  N  N  18  
F3H  "C1'"  "H1'"   SING  N  N  19  
F3H  "F2'"  "C2'"   SING  N  N  20  
F3H  "C3'"  "C2'"   SING  N  N  21  
F3H  "C2'"  "H2'"   SING  N  N  22  
F3H  "C4'"  "C3'"   SING  N  N  23  
F3H  "C3'"  "O3'"   SING  N  N  24  
F3H  "C3'"  "H3'"   SING  N  N  25  
F3H  "O3'"  "HO3'"  SING  N  N  26  
F3H  "C5'"  "C4'"   SING  N  N  27  
F3H  "C4'"  "O4'"   SING  N  N  28  
F3H  "C4'"  "H4'"   SING  N  N  29  
F3H  "O4'"  "C6'"   SING  N  N  30  
F3H  "C5'"  "O5'"   SING  N  N  31  
F3H  "C5'"  "H5'"   SING  N  N  32  
F3H  "C5'"  "H5'A"  SING  N  N  33  
F3H  C5M    H5M     SING  N  N  34  
F3H  C5M    H5MA    SING  N  N  35  
F3H  C5M    H5MB    SING  N  N  36  
F3H  "C6'"  "H6'"   SING  N  N  37  
F3H  "C6'"  "H6'A"  SING  N  N  38  
F3H  OP1    HOP1    SING  N  N  39  
F3H  OP2    HOP2    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
F3H  SMILES            ACDLabs               12.01  "O=P(O)(O)OCC2OCC(N1C(=O)NC(=O)C(=C1)C)C(F)C2O"  
F3H  SMILES_CANONICAL  CACTVS                3.370  "CC1=CN([C@@H]2CO[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]2F)C(=O)NC1=O"  
F3H  SMILES            CACTVS                3.370  "CC1=CN([CH]2CO[CH](CO[P](O)(O)=O)[CH](O)[CH]2F)C(=O)NC1=O"  
F3H  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.0  "CC1=CN(C(=O)NC1=O)[C@@H]2CO[C@@H]([C@H]([C@H]2F)O)COP(=O)(O)O"  
F3H  SMILES            "OpenEye OEToolkits"  1.7.0  "CC1=CN(C(=O)NC1=O)C2COC(C(C2F)O)COP(=O)(O)O"  
F3H  InChI             InChI                 1.03   "InChI=1S/C11H16FN2O8P/c1-5-2-14(11(17)13-10(5)16)6-3-21-7(9(15)8(6)12)4-22-23(18,19)20/h2,6-9,15H,3-4H2,1H3,(H,13,16,17)(H2,18,19,20)/t6-,7-,8+,9-/m1/s1"  
F3H  InChIKey          InChI                 1.03   RHZOVKWYBYFNDA-LURQLKTLSA-N  
#   #
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
F3H  "SYSTEMATIC NAME"  ACDLabs               12.01  "1,5-anhydro-2,3-dideoxy-3-fluoro-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-O-phosphono-D-altritol"  
F3H  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.0  "[(2R,3R,4S,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxan-2-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
F3H  "Create component"   2011-01-04  RCSB  
F3H  "Modify descriptor"  2011-06-04  RCSB  
F3H  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     F3H
_pdbx_chem_comp_synonyms.name        "1,5-anhydro-2,3-dideoxy-3-fluoro-2-(thymin-1-yl)-D-altritol-5-dihydrogenphosphate"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
