HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound SAH

Identifiers

  • Canonical SMILES: 
    N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O
  • IUPAC name: 
    (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid (non-preferred name)
  • InChi: 
    InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
  • InChiKey: 
    ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

25246222 CHEMBL418052 DB01752

RNA-SM complexes

PDB code Deposition date Reference publication
3e5e Aug. 13, 2008 Lu Changrui, Smith Angela M, Fuchs Ryan T, Ding Fang, Rajashankar Kanagalaghatta, Henkin Tina M, Ke Ailong. . Crystal structures of the SAM-III/SMK riboswitch reveal the SAM-dependent translation inhibition mechanism Nature Structural & Molecular Biology
3gx3 April 1, 2009 Montange Rebecca K., Mondragón Estefanía, van Tyne Daria, Garst Andrew D., Ceres Pablo, Batey Robert T.. . Discrimination between Closely Related Cellular Metabolites by the SAM-I Riboswitch Journal of Molecular Biology
3npn June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
6hag Aug. 7, 2018 Weickhmann A Katharina, Keller Heiko, Wurm Jan P, Strebitzer Elisabeth, Juen Michael A, Kremser Johannes, Weinberg Zasha, Kreutz Christoph, Duchardt-Ferner Elke, Wöhnert Jens. . The structure of the SAM/SAH-binding riboswitch Nucleic Acids Research
6lau Nov. 13, 2019 Sun Aiai, Gasser Catherina, Li Fudong, Chen Hao, Mair Stefan, Krasheninina Olga, Micura Ronald, Ren Aiming. . SAM-VI riboswitch structure and signature for ligand discrimination Nature Communications
6lau Nov. 13, 2019 Sun Aiai, Gasser Catherina, Li Fudong, Chen Hao, Mair Stefan, Krasheninina Olga, Micura Ronald, Ren Aiming. . SAM-VI riboswitch structure and signature for ligand discrimination Nature Communications
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 384.12 g/mol
HBA 11
HBD 5
HBA + HBD
AlogP -1.44
TPSA 182.63
RB 7

Radar chart