data_FX3
# 
_chem_comp.id                                    FX3 
_chem_comp.name                                  5-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-alpha-L-ribofuranose 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             ? 
_chem_comp.formula                               "C15 H18 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-12 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        326.299 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FX3 
_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        2VGD 
_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 
FX3 O2     O2   O 0 1 N N N -5.362 -27.470 1.000  -5.362 -27.470 1.000  O2     FX3 1  
FX3 C9     C9   C 0 1 N N N -4.182 -27.299 1.266  -4.182 -27.299 1.266  C9     FX3 2  
FX3 C8     C8   C 0 1 N N N -3.751 -26.144 2.092  -3.751 -26.144 2.092  C8     FX3 3  
FX3 C7     C7   C 0 1 N N N -2.447 -25.865 2.183  -2.447 -25.865 2.183  C7     FX3 4  
FX3 C1     C1   C 0 1 Y N N -1.891 -24.731 2.952  -1.891 -24.731 2.952  C1     FX3 5  
FX3 C6     C6   C 0 1 Y N N -0.717 -24.138 2.483  -0.717 -24.138 2.483  C6     FX3 6  
FX3 C5     C5   C 0 1 Y N N -0.154 -23.066 3.173  -0.154 -23.066 3.173  C5     FX3 7  
FX3 C4     C4   C 0 1 Y N N -0.770 -22.585 4.333  -0.770 -22.585 4.333  C4     FX3 8  
FX3 O4     O4   O 0 1 N N N -0.200 -21.531 4.990  -0.200 -21.531 4.990  O4     FX3 9  
FX3 C3     C3   C 0 1 Y N N -1.950 -23.180 4.808  -1.950 -23.180 4.808  C3     FX3 10 
FX3 O3     O3   O 0 1 N N N -2.564 -22.715 5.956  -2.564 -22.715 5.956  O3     FX3 11 
FX3 C10    C10  C 0 1 N N N -2.681 -23.536 7.127  -2.681 -23.536 7.127  C10    FX3 12 
FX3 C2     C2   C 0 1 Y N N -2.512 -24.257 4.109  -2.512 -24.257 4.109  C2     FX3 13 
FX3 "O5'"  O5*  O 0 1 N N N -3.205 -28.246 0.720  -3.205 -28.246 0.720  "O5'"  FX3 14 
FX3 "C5'"  C5*  C 0 1 N N N -2.236 -28.901 1.551  -2.236 -28.901 1.551  "C5'"  FX3 15 
FX3 "C4'"  C4*  C 0 1 N N S -1.309 -29.787 0.729  -1.309 -29.787 0.729  "C4'"  FX3 16 
FX3 "O4'"  O4*  O 0 1 N N N -0.647 -28.993 -0.260 -0.647 -28.993 -0.260 "O4'"  FX3 17 
FX3 "C3'"  C3*  C 0 1 N N R -2.054 -30.904 0.006  -2.054 -30.904 0.006  "C3'"  FX3 18 
FX3 "O3'"  O3*  O 0 1 N N N -1.484 -32.164 0.372  -1.484 -32.164 0.372  "O3'"  FX3 19 
FX3 "C2'"  C2*  C 0 1 N N S -1.859 -30.606 -1.473 -1.859 -30.606 -1.473 "C2'"  FX3 20 
FX3 "O2'"  O2*  O 0 1 N N N -1.558 -31.776 -2.239 -1.558 -31.776 -2.239 "O2'"  FX3 21 
FX3 "C1'"  C1*  C 0 1 N N R -0.689 -29.638 -1.535 -0.689 -29.638 -1.535 "C1'"  FX3 22 
FX3 OXT    OXT  O 0 1 N Y N 0.607  -29.926 -1.728 0.607  -29.926 -1.728 OXT    FX3 23 
FX3 H8     H8   H 0 1 N N N -4.479 -25.539 2.611  -4.479 -25.539 2.611  H8     FX3 24 
FX3 H7     H7   H 0 1 N N N -1.755 -26.509 1.661  -1.755 -26.509 1.661  H7     FX3 25 
FX3 H6     H6   H 0 1 N N N -0.245 -24.510 1.586  -0.245 -24.510 1.586  H6     FX3 26 
FX3 H2     H2   H 0 1 N N N -3.422 -24.718 4.464  -3.422 -24.718 4.464  H2     FX3 27 
FX3 H5     H5   H 0 1 N N N 0.755  -22.608 2.813  0.755  -22.608 2.813  H5     FX3 28 
FX3 H4     H4   H 0 1 N N N -0.068 -21.760 5.902  -0.068 -21.760 5.902  H4     FX3 29 
FX3 H101   1H10 H 0 0 N N N -2.711 -24.595 6.831  -2.711 -24.595 6.831  H101   FX3 30 
FX3 H102   2H10 H 0 0 N N N -1.816 -23.363 7.784  -1.816 -23.363 7.784  H102   FX3 31 
FX3 H103   3H10 H 0 0 N N N -3.606 -23.279 7.664  -3.606 -23.279 7.664  H103   FX3 32 
FX3 "H5'1" 1H5* H 0 0 N N N -1.634 -28.137 2.065  -1.634 -28.137 2.065  "H5'1" FX3 33 
FX3 "H5'2" 2H5* H 0 0 N N N -2.770 -29.534 2.275  -2.770 -29.534 2.275  "H5'2" FX3 34 
FX3 "H4'"  H4*  H 0 1 N N N -0.596 -30.241 1.432  -0.596 -30.241 1.433  "H4'"  FX3 35 
FX3 "H3'"  H3*  H 0 1 N N N -3.123 -30.954 0.261  -3.123 -30.954 0.261  "H3'"  FX3 36 
FX3 "H1'"  H1*  H 0 1 N N N -0.961 -29.156 -2.485 -0.961 -29.156 -2.486 "H1'"  FX3 37 
FX3 HA     HA   H 0 1 N N N -1.358 -32.693 -0.407 -1.358 -32.693 -0.407 HA     FX3 38 
FX3 "H2'"  H2*  H 0 1 N N N -2.785 -30.196 -1.903 -2.785 -30.197 -1.903 "H2'"  FX3 39 
FX3 HB     HB   H 0 1 N N N -1.491 -31.545 -3.158 -1.491 -31.545 -3.158 HB     FX3 40 
FX3 HOT    HOT  H 0 1 N N N 0.781  -29.994 -2.659 0.781  -29.994 -2.659 HOT    FX3 41 
# 
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 
FX3 O2    C9     DOUB N N 1  
FX3 C9    C8     SING N N 2  
FX3 C9    "O5'"  SING N N 3  
FX3 C8    C7     DOUB N E 4  
FX3 C7    C1     SING N N 5  
FX3 C1    C6     SING N N 6  
FX3 C1    C2     DOUB N N 7  
FX3 C6    C5     DOUB Y N 8  
FX3 C5    C4     SING Y N 9  
FX3 C4    O4     SING Y N 10 
FX3 C4    C3     DOUB N N 11 
FX3 C3    O3     SING Y N 12 
FX3 C3    C2     SING N N 13 
FX3 O3    C10    SING N N 14 
FX3 "O5'" "C5'"  SING Y N 15 
FX3 "C5'" "C4'"  SING N N 16 
FX3 "C4'" "O4'"  SING N N 17 
FX3 "C4'" "C3'"  SING Y N 18 
FX3 "O4'" "C1'"  SING N N 19 
FX3 "C3'" "O3'"  SING N N 20 
FX3 "C3'" "C2'"  SING N N 21 
FX3 "C2'" "O2'"  SING N N 22 
FX3 "C2'" "C1'"  SING N N 23 
FX3 "C1'" OXT    SING N N 24 
FX3 C8    H8     SING N N 25 
FX3 C7    H7     SING N N 26 
FX3 C6    H6     SING N N 27 
FX3 C2    H2     SING N N 28 
FX3 C5    H5     SING N N 29 
FX3 O4    H4     SING N N 30 
FX3 C10   H101   SING N N 31 
FX3 C10   H102   SING N N 32 
FX3 C10   H103   SING N N 33 
FX3 "C5'" "H5'1" SING N N 34 
FX3 "C5'" "H5'2" SING N N 35 
FX3 "C4'" "H4'"  SING N N 36 
FX3 "C3'" "H3'"  SING N N 37 
FX3 "C1'" "H1'"  SING N N 38 
FX3 "O3'" HA     SING N N 39 
FX3 "C2'" "H2'"  SING N N 40 
FX3 "O2'" HB     SING N N 41 
FX3 OXT   HOT    SING N N 42 
# 
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 
FX3 SMILES           ACDLabs              10.04 O=C(OCC1OC(O)C(O)C1O)\C=C\c2ccc(O)c(OC)c2                                                                                                     
FX3 InChI            InChI                1.02b InChI=1/C15H18O8/c1-21-10-6-8(2-4-9(10)16)3-5-12(17)22-7-11-13(18)14(19)15(20)23-11/h2-6,11,13-16,18-20H,7H2,1H3/b5-3+/t11-,13-,14-,15+/m0/s1 
FX3 InChIKey         InChI                1.02b BDEXCUQHBTVULQ-NNDRJBMQBQ                                                                                                                     
FX3 SMILES_CANONICAL CACTVS               3.341 COc1cc(/C=C/C(=O)OC[C@@H]2O[C@@H](O)[C@@H](O)[C@H]2O)ccc1O                                                                                    
FX3 SMILES           CACTVS               3.341 COc1cc(C=CC(=O)OC[CH]2O[CH](O)[CH](O)[CH]2O)ccc1O                                                                                             
FX3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1cc(ccc1O)\C=C\C(=O)OC[C@H]2[C@@H]([C@@H]([C@@H](O2)O)O)O                                                                                  
FX3 SMILES           "OpenEye OEToolkits" 1.5.0 COc1cc(ccc1O)C=CC(=O)OCC2C(C(C(O2)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 
FX3 "SYSTEMATIC NAME" ACDLabs              10.04 5-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-alpha-L-ribofuranose                           
FX3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S,3R,4S,5R)-3,4,5-trihydroxyoxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate" 
# 
