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HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound BLS

Identifiers

  • Canonical SMILES: 
    CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(O)=O)N2C=CC(=NC2=O)N)C(N)=N
  • IUPAC name: 
    4-amino-1-[4-({(3S)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl}amino)-2,3,4-trideoxy-beta-D-erythro-hex-2-enopyranuronosyl]pyrimidin-2(1H)-one
  • InChi: 
    InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1
  • InChiKey: 
    CXNPLSGKWMLZPZ-ZNIXKSQXSA-N
  • SMARTS: 
    [#6]-[#7](-[#6]-[#6]-[#6@H](-[#7])-[#6]-[#6](=[#8])-[#7]-[#6@H]1-[#6]=[#6]-[#6@@H](-[#8]-[#6@@H]-1-[#6](-[#8])=[#8])-[#7]1:[#6]:[#6]:[#6](:[#7]:[#6]:1=[#8])-[#7])-[#6](-[#7])=[#7]

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

PubChem Logo 170012 ChEMBL Logo CHEMBL476894 PDB Logo BLS

RNA-SM complexes

PDB code Deposition date Reference publication
1kc8 Nov. 7, 2001 Hansen Jeffrey L., Moore Peter B., Steitz Thomas A.. 2003. Structures of Five Antibiotics Bound at the Peptidyl Transferase Center of the Large Ribosomal Subunit Journal of Molecular Biology
1kc8 Nov. 7, 2001 Hansen Jeffrey L., Moore Peter B., Steitz Thomas A.. 2003. Structures of Five Antibiotics Bound at the Peptidyl Transferase Center of the Large Ribosomal Subunit Journal of Molecular Biology
4u56 July 24, 2014 Garreau de Loubresse Nicolas, Prokhorova Irina, Holtkamp Wolf, Rodnina Marina V., Yusupova Gulnara, Yusupov Marat. 2014. Structural basis for the inhibition of the eukaryotic ribosome Nature
4u56 July 24, 2014 Garreau de Loubresse Nicolas, Prokhorova Irina, Holtkamp Wolf, Rodnina Marina V., Yusupova Gulnara, Yusupov Marat. 2014. Structural basis for the inhibition of the eukaryotic ribosome Nature
4v9q June 12, 2013 Svidritskiy Egor, Ling Clarence, Ermolenko Dmitri N., Korostelev Andrei A.. 2013. Blasticidin S inhibits translation by trapping deformed tRNA on the ribosome Proceedings of the National Academy of Sciences
4v9q June 12, 2013 Svidritskiy Egor, Ling Clarence, Ermolenko Dmitri N., Korostelev Andrei A.. 2013. Blasticidin S inhibits translation by trapping deformed tRNA on the ribosome Proceedings of the National Academy of Sciences
6b4v Sept. 27, 2017 Svidritskiy Egor, Korostelev Andrei A.. 2018. Mechanism of Inhibition of Translation Termination by Blasticidin S Journal of Molecular Biology
6b4v Sept. 27, 2017 Svidritskiy Egor, Korostelev Andrei A.. 2018. Mechanism of Inhibition of Translation Termination by Blasticidin S Journal of Molecular Biology
6boh Nov. 20, 2017 Svidritskiy Egor, Korostelev Andrei A.. 2018. Conformational Control of Translation Termination on the 70S Ribosome Structure
6boh Nov. 20, 2017 Svidritskiy Egor, Korostelev Andrei A.. 2018. Conformational Control of Translation Termination on the 70S Ribosome Structure
7nwg March 16, 2021 Powers Kyle T, Stevenson-Jones Flint, Yadav Sathish K N, Amthor Beate, Bufton Joshua C, Borucu Ufuk, Shen Dakang, Becker Jonas P, Lavysh Daria, Hentze Matthias W, Kulozik Andreas E, Neu-Yilik Gabriele, Schaffitzel Christiane. 2021. Blasticidin S inhibits mammalian translation and enhances production of protein encoded by nonsense mRNA Nucleic Acids Research
7nwi March 16, 2021 Powers Kyle T, Stevenson-Jones Flint, Yadav Sathish K N, Amthor Beate, Bufton Joshua C, Borucu Ufuk, Shen Dakang, Becker Jonas P, Lavysh Daria, Hentze Matthias W, Kulozik Andreas E, Neu-Yilik Gabriele, Schaffitzel Christiane. 2021. Blasticidin S inhibits mammalian translation and enhances production of protein encoded by nonsense mRNA Nucleic Acids Research
7q0r Oct. 16, 2021 Zgadzay Yury, Kolosova Olga, Stetsenko Artem, Wu Cheng, Bruchlen David, Usachev Konstantin, Validov Shamil, Jenner Lasse, Rogachev Andrey, Yusupova Gulnara, Sachs Matthew S., Guskov Albert, Yusupov Marat. 2022. E-site drug specificity of the human pathogen Candida albicans ribosome Science Advances

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 422.20 g/mol
HBA 8
HBD 6
HBA + HBD
AlogP -2.22
TPSA 215.67
RB 8

Radar chart