Fluorine in PDB 3rll: Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide

The structure of Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide, PDB code: 3rll was solved by C.E.Bohl, C.B.Duke, A.Jones, J.T.Dalton, D.D.Miller, with X-Ray Crystallography technique. A brief refinement statistics is given in the table below:

Resolution Low / High (Å)	22.02 / 1.70
Space group	P 21 21 21
Cell size a, b, c (Å), α, β, γ (°)	54.450, 66.420, 69.950, 90.00, 90.00, 90.00
R / Rfree (%)	23.5 / 26.3

The binding sites of Fluorine atom in the Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide (pdb code 3rll). This binding sites where shown within 5.0 Angstroms radius around Fluorine atom.
In total 3 binding sites of Fluorine where determined in the Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide, PDB code: 3rll:
Jump to Fluorine binding site number: 1; 2; 3;

Fluorine binding site 1 out of 3 in the Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide


Mono view


Stereo pair view

A full contact list of Fluorine with other atoms in the F binding site number 1 of Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide within 5.0Å range: probe atom residue distance (Å) B Occ A:F1 b:24.5 occ:1.00 FAF A:RLL1 0.0 24.5 1.0 CBF A:RLL1 1.3 22.3 1.0 FAH A:RLL1 2.1 23.6 1.0 FAG A:RLL1 2.2 23.2 1.0 CBB A:RLL1 2.4 21.2 1.0 CAS A:RLL1 2.7 21.2 1.0 CD1 A:LEU873 3.4 23.7 1.0 SD A:MET787 3.6 22.4 1.0 CAY A:RLL1 3.6 19.5 1.0 CE A:MET787 3.9 21.7 1.0 CE2 A:PHE764 4.0 17.5 1.0 CG2 A:VAL746 4.1 16.1 1.0 CAX A:RLL1 4.1 21.6 1.0 OAD A:RLL1 4.1 23.4 1.0 CD2 A:LEU873 4.2 21.2 1.0 CAI A:RLL1 4.2 19.5 1.0 SD A:MET742 4.4 23.6 1.0 CG A:LEU873 4.4 22.4 1.0 CD2 A:PHE764 4.7 18.1 1.0 CAN A:RLL1 4.8 20.7 1.0 CA A:VAL746 4.9 17.2 1.0 CAM A:RLL1 4.9 20.9 1.0 NAU A:RLL1 4.9 21.1 1.0 CAW A:RLL1 4.9 21.6 1.0 NAB A:RLL1 5.0 15.8 1.0 CZ A:PHE764 5.0 20.0 1.0

Fluorine binding site 2 out of 3 in the Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide


Mono view


Stereo pair view

A full contact list of Fluorine with other atoms in the F binding site number 2 of Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide within 5.0Å range: probe atom residue distance (Å) B Occ A:F1 b:23.2 occ:1.00 FAG A:RLL1 0.0 23.2 1.0 CBF A:RLL1 1.3 22.3 1.0 FAF A:RLL1 2.2 24.5 1.0 FAH A:RLL1 2.2 23.6 1.0 CBB A:RLL1 2.3 21.2 1.0 CAY A:RLL1 3.1 19.5 1.0 CAI A:RLL1 3.2 19.5 1.0 CAS A:RLL1 3.3 21.2 1.0 N A:VAL746 3.3 17.4 1.0 CB A:MET745 3.3 17.3 1.0 C A:MET745 3.4 17.4 1.0 CG2 A:VAL746 3.7 16.1 1.0 CA A:VAL746 3.7 17.2 1.0 NAB A:RLL1 3.7 15.8 1.0 O A:MET745 3.8 19.1 1.0 CA A:MET745 4.0 16.5 1.0 O A:MET742 4.1 19.0 1.0 SD A:MET742 4.2 23.6 1.0 CAN A:RLL1 4.3 20.7 1.0 CB A:VAL746 4.3 18.9 1.0 CAX A:RLL1 4.5 21.6 1.0 CAL A:RLL1 4.5 17.4 1.0 CG A:MET745 4.6 18.1 1.0 CD1 A:LEU873 4.7 23.7 1.0 SD A:MET787 4.8 22.4 1.0 N A:MET745 4.9 16.3 1.0 CAM A:RLL1 4.9 20.9 1.0 CAK A:RLL1 5.0 17.8 1.0

Fluorine binding site 3 out of 3 in the Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide


Mono view


Stereo pair view

A full contact list of Fluorine with other atoms in the F binding site number 3 of Crystal Structure of the T877A Androgen Receptor Ligand Binding Domain in Complex with (S)-N-(4-Cyano-3-(Trifluoromethyl)Phenyl)-3-(4- Cyanonaphthalen-1-Yloxy)-2-Hydroxy-2-Methylpropanamide within 5.0Å range: probe atom residue distance (Å) B Occ A:F1 b:23.6 occ:1.00 FAH A:RLL1 0.0 23.6 1.0 CBF A:RLL1 1.3 22.3 1.0 FAF A:RLL1 2.1 24.5 1.0 FAG A:RLL1 2.2 23.2 1.0 CBB A:RLL1 2.4 21.2 1.0 CAI A:RLL1 2.8 19.5 1.0 CAY A:RLL1 2.9 19.5 1.0 NAB A:RLL1 3.2 15.8 1.0 CE2 A:PHE764 3.4 17.5 1.0 CAS A:RLL1 3.5 21.2 1.0 CD2 A:PHE764 3.7 18.1 1.0 CB A:MET749 3.7 18.6 1.0 CE A:MET749 3.7 23.2 1.0 CG A:MET749 3.8 18.8 1.0 SD A:MET787 3.8 22.4 1.0 O A:MET745 4.0 19.1 1.0 CA A:VAL746 4.2 17.2 1.0 CAN A:RLL1 4.3 20.7 1.0 C A:MET745 4.3 17.4 1.0 N A:VAL746 4.4 17.4 1.0 CE A:MET787 4.4 21.7 1.0 CZ A:PHE764 4.6 20.0 1.0 SD A:MET749 4.6 22.0 1.0 CG2 A:VAL746 4.6 16.1 1.0 CAX A:RLL1 4.7 21.6 1.0 CB A:MET745 4.8 17.3 1.0 CG A:PHE764 4.9 18.1 1.0 CAM A:RLL1 5.0 20.9 1.0

C.B.Duke, A.Jones, C.E.Bohl, J.T.Dalton, D.D.Miller. Unexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications For Future Drug Targets. J.Med.Chem. V. 54 3973 2011.
ISSN: ISSN 0022-2623
PubMed: 21506597
DOI: 10.1021/JM2000097