data_FMD
# 
_chem_comp.id                                    FMD 
_chem_comp.name                                  4-((3R,4S,5R)-4-AMINO-3,5-DIHYDROXY-HEX-1-YNYL)-5-FLUORO-3-[1-(3-METHOXY-1H-PYRROL-2-YL)-METH-(Z)-YLIDENE]-1,3-DIHYDRO-INDOL-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H20 F N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-10-24 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        385.389 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FMD 
_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        1R78 
_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 
FMD F17  F17  F 0 1 N N N 16.820 -6.294  12.779 -3.952 -0.493 1.769  F17  FMD 1  
FMD C1   C1   C 0 1 Y N N 16.024 -7.208  13.363 -3.633 -0.327 0.466  C1   FMD 2  
FMD C2   C2   C 0 1 Y N N 14.877 -7.607  12.658 -2.293 -0.248 0.080  C2   FMD 3  
FMD C18  C18  C 0 1 N N N 14.588 -7.039  11.402 -1.252 -0.342 1.058  C18  FMD 4  
FMD C19  C19  C 0 1 N N N 14.326 -6.571  10.333 -0.398 -0.419 1.860  C19  FMD 5  
FMD C20  C20  C 0 1 N N R 13.963 -6.027  9.086  0.672  -0.516 2.865  C20  FMD 6  
FMD O27  O27  O 0 1 N N N 14.161 -4.611  9.140  1.943  -0.407 2.220  O27  FMD 7  
FMD C23  C23  C 0 1 N N S 14.603 -6.731  7.862  0.519  0.614  3.884  C23  FMD 8  
FMD N28  N28  N 0 1 N N N 15.006 -8.116  8.140  -0.786 0.502  4.547  N28  FMD 9  
FMD C24  C24  C 0 1 N N R 13.526 -6.726  6.761  1.632  0.513  4.929  C24  FMD 10 
FMD O26  O26  O 0 1 N N N 14.086 -6.757  5.441  1.544  -0.745 5.599  O26  FMD 11 
FMD C25  C25  C 0 1 N N N 12.550 -5.532  6.867  1.478  1.645  5.948  C25  FMD 12 
FMD C3   C3   C 0 1 Y N N 14.035 -8.616  13.321 -1.977 -0.082 -1.277 C3   FMD 13 
FMD C4   C4   C 0 1 Y N N 14.416 -9.125  14.601 -2.999 0.015  -2.231 C4   FMD 14 
FMD N9   N9   N 0 1 N N N 13.440 -10.033 14.962 -2.414 0.180  -3.481 N9   FMD 15 
FMD C8   C8   C 0 1 N N N 12.430 -10.203 13.999 -1.074 0.201  -3.384 C8   FMD 16 
FMD O10  O10  O 0 1 N N N 11.492 -10.964 14.129 -0.298 0.332  -4.315 O10  FMD 17 
FMD C5   C5   C 0 1 Y N N 15.558 -8.685  15.255 -4.324 -0.066 -1.821 C5   FMD 18 
FMD C6   C6   C 0 1 Y N N 16.366 -7.720  14.623 -4.633 -0.235 -0.485 C6   FMD 19 
FMD C7   C7   C 0 1 N N N 12.887 -9.235  12.944 -0.708 0.044  -2.019 C7   FMD 20 
FMD C11  C11  C 0 1 N N N 12.151 -9.008  11.689 0.575  0.011  -1.494 C11  FMD 21 
FMD C12  C12  C 0 1 Y N N 10.890 -9.521  11.157 1.675  0.300  -2.314 C12  FMD 22 
FMD C13  C13  C 0 1 Y N N 10.257 -9.222  9.966  2.942  -0.277 -2.234 C13  FMD 23 
FMD O21  O21  O 0 1 N N N 10.702 -8.329  9.010  3.342  -1.228 -1.353 O21  FMD 24 
FMD C22  C22  C 0 1 N N N 10.250 -8.469  7.653  4.709  -1.518 -1.650 C22  FMD 25 
FMD C14  C14  C 0 1 Y N N 9.036  -10.021 9.977  3.721  0.306  -3.242 C14  FMD 26 
FMD C15  C15  C 0 1 Y N N 9.023  -10.745 11.126 2.951  1.207  -3.898 C15  FMD 27 
FMD N16  N16  N 0 1 Y N N 10.141 -10.458 11.840 1.710  1.219  -3.348 N16  FMD 28 
FMD H20  H20  H 0 1 N N N 12.881 -6.227  8.907  0.605  -1.477 3.376  H20  FMD 29 
FMD H27  H27  H 0 1 N N N 13.916 -4.244  8.299  1.960  0.454  1.782  H27  FMD 30 
FMD H23  H23  H 0 1 N N N 15.534 -6.192  7.569  0.586  1.575  3.373  H23  FMD 31 
FMD H281 1H28 H 0 0 N N N 14.221 -8.658  8.502  -0.803 -0.396 5.004  H281 FMD 32 
FMD H282 2H28 H 0 0 N N N 15.427 -8.579  7.335  -0.802 1.198  5.277  H282 FMD 33 
FMD H24  H24  H 0 1 N N N 12.950 -7.665  6.933  2.601  0.597  4.437  H24  FMD 34 
FMD H26  H26  H 0 1 N N N 13.422 -6.754  4.762  0.674  -0.778 6.020  H26  FMD 35 
FMD H251 1H25 H 0 0 N N N 13.106 -4.566  6.882  2.271  1.573  6.693  H251 FMD 36 
FMD H252 2H25 H 0 0 N N N 11.770 -5.528  6.070  1.545  2.605  5.437  H252 FMD 37 
FMD H253 3H25 H 0 0 N N N 12.083 -5.491  7.879  0.509  1.561  6.440  H253 FMD 38 
FMD HN9  HN9  H 0 1 N N N 13.463 -10.529 15.853 -2.906 0.269  -4.312 HN9  FMD 39 
FMD HC5  HC5  H 0 1 N N N 15.816 -9.090  16.248 -5.117 0.003  -2.551 HC5  FMD 40 
FMD HC6  HC6  H 0 1 N N N 17.281 -7.360  15.123 -5.667 -0.297 -0.180 HC6  FMD 41 
FMD H11  H11  H 0 1 N N N 12.650 -8.304  11.002 0.727  -0.237 -0.454 H11  FMD 42 
FMD H221 1H22 H 0 0 N N N 9.135  -8.473  7.647  5.076  -2.281 -0.963 H221 FMD 43 
FMD H222 2H22 H 0 0 N N N 10.609 -7.748  6.882  4.789  -1.882 -2.674 H222 FMD 44 
FMD H223 3H22 H 0 0 N N N 10.475 -9.505  7.307  5.305  -0.612 -1.538 H223 FMD 45 
FMD H14  H14  H 0 1 N N N 8.234  -10.071 9.221  4.754  0.079  -3.457 H14  FMD 46 
FMD H15  H15  H 0 1 N N N 8.233  -11.452 11.430 3.274  1.818  -4.728 H15  FMD 47 
FMD H16  H16  H 0 1 N N N 10.379 -10.876 12.739 0.970  1.777  -3.635 H16  FMD 48 
# 
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 
FMD F17 C1   SING N N 1  
FMD C1  C2   DOUB Y N 2  
FMD C1  C6   SING Y N 3  
FMD C2  C18  SING N N 4  
FMD C2  C3   SING Y N 5  
FMD C18 C19  TRIP N N 6  
FMD C19 C20  SING N N 7  
FMD C20 O27  SING N N 8  
FMD C20 C23  SING N N 9  
FMD C20 H20  SING N N 10 
FMD O27 H27  SING N N 11 
FMD C23 N28  SING N N 12 
FMD C23 C24  SING N N 13 
FMD C23 H23  SING N N 14 
FMD N28 H281 SING N N 15 
FMD N28 H282 SING N N 16 
FMD C24 O26  SING N N 17 
FMD C24 C25  SING N N 18 
FMD C24 H24  SING N N 19 
FMD O26 H26  SING N N 20 
FMD C25 H251 SING N N 21 
FMD C25 H252 SING N N 22 
FMD C25 H253 SING N N 23 
FMD C3  C4   DOUB Y N 24 
FMD C3  C7   SING N N 25 
FMD C4  N9   SING N N 26 
FMD C4  C5   SING Y N 27 
FMD N9  C8   SING N N 28 
FMD N9  HN9  SING N N 29 
FMD C8  O10  DOUB N N 30 
FMD C8  C7   SING N N 31 
FMD C5  C6   DOUB Y N 32 
FMD C5  HC5  SING N N 33 
FMD C6  HC6  SING N N 34 
FMD C7  C11  DOUB N Z 35 
FMD C11 C12  SING N N 36 
FMD C11 H11  SING N N 37 
FMD C12 C13  DOUB Y N 38 
FMD C12 N16  SING Y N 39 
FMD C13 O21  SING N N 40 
FMD C13 C14  SING Y N 41 
FMD O21 C22  SING N N 42 
FMD C22 H221 SING N N 43 
FMD C22 H222 SING N N 44 
FMD C22 H223 SING N N 45 
FMD C14 C15  DOUB Y N 46 
FMD C14 H14  SING N N 47 
FMD C15 N16  SING Y N 48 
FMD C15 H15  SING N N 49 
FMD N16 H16  SING N N 50 
# 
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 
FMD SMILES           ACDLabs              10.04 Fc1c(C#CC(O)C(N)C(O)C)c\2c(cc1)NC(=O)C/2=C/c3c(OC)ccn3                                                                                                                                   
FMD InChI            InChI                1.02b InChI=1/C20H20FN3O4/c1-10(25)19(22)16(26)6-3-11-13(21)4-5-14-18(11)12(20(27)24-14)9-15-17(28-2)7-8-23-15/h4-5,7-10,16,19,23,25-26H,22H2,1-2H3,(H,24,27)/b12-9-/t10-,16-,19+/m1/s1/f/h24H 
FMD InChIKey         InChI                1.02b RAKYKJWUUUKCCW-NPWILADNDZ                                                                                                                                                                
FMD SMILES_CANONICAL CACTVS               3.341 COc1cc[nH]c1/C=C/2C(=O)Nc3ccc(F)c(C#C[C@@H](O)[C@@H](N)[C@@H](C)O)c/23                                                                                                                   
FMD SMILES           CACTVS               3.341 COc1cc[nH]c1C=C2C(=O)Nc3ccc(F)c(C#C[CH](O)[CH](N)[CH](C)O)c23                                                                                                                            
FMD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]([C@@H]([C@@H](C#Cc1c(ccc2c1/C(=C/c3c(cc[nH]3)OC)/C(=O)N2)F)O)N)O                                                                                                                  
FMD SMILES           "OpenEye OEToolkits" 1.5.0 CC(C(C(C#Cc1c(ccc2c1C(=Cc3c(cc[nH]3)OC)C(=O)N2)F)O)N)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 
FMD "SYSTEMATIC NAME" ACDLabs              10.04 (3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxyhex-1-yn-1-yl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one 
FMD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxy-hex-1-ynyl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one               
# 
