HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound TEL

Identifiers

  • Canonical SMILES: 
    CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@H]3N(CCCCn4cnc(c4)c5cccnc5)C(=O)O[C@]13C)OC
  • IUPAC name: 
    (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-1-{4-[4-(pyridin-3-yl)-1H-imidazol-1-yl]butyl}tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranoside
  • InChi: 
    InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1
  • InChiKey: 
    LJVAJPDWBABPEJ-PNUFFHFMSA-N
  • SMARTS: 
    [#6]-[#6]-[#6@H]1-[#8]-[#6](=[#8])-[#6@H](-[#6])-[#6](=[#8])-[#6@H](-[#6])-[#6@@H](-[#8]-[#6@@H]2-[#8]-[#6@H](-[#6])-[#6]-[#6@@H](-[#6@H]-2-[#8])-[#7](-[#6])-[#6])-[#6@@](-[#6])(-[#6]-[#6@@H](-[#6])-[#6](=[#8])-[#6@H](-[#6])-[#6@H]2-[#7](-[#6]-[#6]-[#6]-[#6]-[#7]3:[#6]:[#7]:[#6](:[#6]:3)-[#6]3:[#6]:[#6]:[#6]:[#7]:[#6]:3)-[#6](=[#8])-[#8]-[#6@]-1-2-[#6])-[#8]-[#6]

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

3002190 CHEMBL1136 DB00976

RNA-SM complexes

PDB code Deposition date Reference publication
1p9x May 13, 2003 Berisio Rita, Harms Joerg, Schluenzen Frank, Zarivach Raz, Hansen Harly A. S., Fucini Paola, Yonath Ada. . Structural Insight into the Antibiotic Action of Telithromycin against Resistant Mutants Journal of Bacteriology
1yij Jan. 12, 2005 Tu Daqi, Blaha Gregor, Moore Peter B., Steitz Thomas A.. . Structures of MLSBK Antibiotics Bound to Mutated Large Ribosomal Subunits Provide a Structural Explanation for Resistance Cell
4v7s Aug. 5, 2010 Dunkle Jack A., Xiong Liqun, Mankin Alexander S., Cate Jamie H. D.. . Structures of the Escherichia coli ribosome with antibiotics bound near the peptidyl transferase center explain spectra of drug action Proceedings of the National Academy of Sciences
4v7z Aug. 18, 2010 Bulkley David, Innis C. Axel, Blaha Gregor, Steitz Thomas A.. . Revisiting the structures of several antibiotics bound to the bacterial ribosome Proceedings of the National Academy of Sciences
4v7z Aug. 18, 2010 Bulkley David, Innis C. Axel, Blaha Gregor, Steitz Thomas A.. . Revisiting the structures of several antibiotics bound to the bacterial ribosome Proceedings of the National Academy of Sciences
4wf9 Sept. 14, 2014 Eyal Zohar, Matzov Donna, Krupkin Miri, Wekselman Itai, Paukner Susanne, Zimmerman Ella, Rozenberg Haim, Bashan Anat, Yonath Ada. . Structural insights into species-specific features of the ribosome from the pathogen Staphylococcus aureus Proceedings of the National Academy of Sciences
6ha1 Aug. 7, 2018 Crowe-McAuliffe Caillan, Graf Michael, Huter Paul, Takada Hiraku, Abdelshahid Maha, Nováček Jiří, Murina Victoriia, Atkinson Gemma C., Hauryliuk Vasili, Wilson Daniel N.. . Structural basis for antibiotic resistance mediated by the Bacillus subtilis ABCF ATPase VmlR Proceedings of the National Academy of Sciences
6ha8 Aug. 7, 2018 Crowe-McAuliffe Caillan, Graf Michael, Huter Paul, Takada Hiraku, Abdelshahid Maha, Nováček Jiří, Murina Victoriia, Atkinson Gemma C., Hauryliuk Vasili, Wilson Daniel N.. . Structural basis for antibiotic resistance mediated by the Bacillus subtilis ABCF ATPase VmlR Proceedings of the National Academy of Sciences
6xhy June 19, 2020 Svetlov Maxim S., Syroegin Egor A., Aleksandrova Elena V., Atkinson Gemma C., Gregory Steven T., Mankin Alexander S., Polikanov Yury S.. . Structure of Erm-modified 70S ribosome reveals the mechanism of macrolide resistance Nature Chemical Biology
6xhy June 19, 2020 Svetlov Maxim S., Syroegin Egor A., Aleksandrova Elena V., Atkinson Gemma C., Gregory Steven T., Mankin Alexander S., Polikanov Yury S.. . Structure of Erm-modified 70S ribosome reveals the mechanism of macrolide resistance Nature Chemical Biology
7azy Nov. 17, 2020 Svetlov Maxim S., Koller Timm O., Meydan Sezen, Shankar Vaishnavi, Klepacki Dorota, Polacek Norbert, Guydosh Nicholas R., Vázquez-Laslop Nora, Wilson Daniel N., Mankin Alexander S.. . Context-specific action of macrolide antibiotics on the eukaryotic ribosome Nature Communications
7nsq March 8, 2021 Beckert Bertrand, Leroy Elodie C., Sothiselvam Shanmugapriya, Bock Lars V., Svetlov Maxim S., Graf Michael, Arenz Stefan, Abdelshahid Maha, Seip Britta, Grubmüller Helmut, Mankin Alexander S., Innis C. Axel, Vázquez-Laslop Nora, Wilson Daniel N.. . Structural and mechanistic basis for translation inhibition by macrolide and ketolide antibiotics Nature Communications
8fc3 Dec. 1, 2022 Chen Chih-Wei, Leimer Nadja, Syroegin Egor A., Dunand Clémence, Bulman Zackery P., Lewis Kim, Polikanov Yury S., Svetlov Maxim S.. . Structural insights into the mechanism of overcoming Erm-mediated resistance by macrolides acting together with hygromycin-A Nature Communications
8fc3 Dec. 1, 2022 Chen Chih-Wei, Leimer Nadja, Syroegin Egor A., Dunand Clémence, Bulman Zackery P., Lewis Kim, Polikanov Yury S., Svetlov Maxim S.. . Structural insights into the mechanism of overcoming Erm-mediated resistance by macrolides acting together with hygromycin-A Nature Communications
8fc6 Dec. 1, 2022 Chen Chih-Wei, Leimer Nadja, Syroegin Egor A., Dunand Clémence, Bulman Zackery P., Lewis Kim, Polikanov Yury S., Svetlov Maxim S.. . Structural insights into the mechanism of overcoming Erm-mediated resistance by macrolides acting together with hygromycin-A Nature Communications
8fc6 Dec. 1, 2022 Chen Chih-Wei, Leimer Nadja, Syroegin Egor A., Dunand Clémence, Bulman Zackery P., Lewis Kim, Polikanov Yury S., Svetlov Maxim S.. . Structural insights into the mechanism of overcoming Erm-mediated resistance by macrolides acting together with hygromycin-A Nature Communications
9o3i April 7, 2025 Syroegin Egor A., Aleksandrova Elena V., Kruglov Artem A., Paranjpe Madhura N., Svetlov Maxim S., Polikanov Yury S.. . Structural insights into context-specific inhibition of bacterial translation by macrolides []
9o3i April 7, 2025 Syroegin Egor A., Aleksandrova Elena V., Kruglov Artem A., Paranjpe Madhura N., Svetlov Maxim S., Polikanov Yury S.. . Structural insights into context-specific inhibition of bacterial translation by macrolides []

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 811.47 g/mol
HBA 13
HBD 1
HBA + HBD
AlogP 4.93
TPSA 171.85
RB 11

Radar chart