HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound HGR

Identifiers

  • Canonical SMILES: 
    CC(=O)[C@H]1O[C@@H](OC2=CCC(=CC2=O)/C=C(C)/C(=O)N[C@@H]3[C@H](O)[C@@H](O)[C@H]4OCO[C@H]4[C@@H]3O)[C@@H](O)[C@@H]1O
  • IUPAC name: 
    (2E)-3-{4-[(6-deoxy-beta-D-arabino-hexofuranosyl-5-ulose)oxy]-3-oxocyclohexa-1,4-dien-1-yl}-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl]prop-2-enamide
  • InChi: 
    InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h4-6,13-21,23,27-31H,3,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14+,15-,16-,17+,18+,19-,20+,21-,23-/m1/s1
  • InChiKey: 
    LDTRVHIISSLXOQ-IIHALWDASA-N
  • SMARTS: 
    [#6]-[#6](=[#8])-[#6@H]1-[#8]-[#6@@H](-[#8]-[#6]2=[#6]-[#6]-[#6](=[#6]-[#6]-2=[#8])/[#6]=[#6](\[#6])-[#6](=[#8])-[#7]-[#6@@H]2-[#6@H](-[#8])-[#6@@H](-[#8])-[#6@H]3-[#8]-[#6]-[#8]-[#6@H]-3-[#6@@H]-2-[#8])-[#6@@H](-[#8])-[#6@@H]-1-[#8]

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

137349514

RNA-SM complexes

PDB code Deposition date Reference publication
5dm7 Sept. 8, 2015 Kaminishi Tatsuya, Schedlbauer Andreas, Fabbretti Attilio, Brandi Letizia, Ochoa-Lizarralde Borja, He Cheng-Guang, Milón Pohl, Connell Sean R., Gualerzi Claudio O., Fucini Paola. . Crystallographic characterization of the ribosomal binding site and molecular mechanism of action of Hygromycin A Nucleic Acids Research
5dox Sept. 11, 2015 Polikanov Yury S., Starosta Agata L., Juette Manuel F., Altman Roger B., Terry Daniel S., Lu Wanli, Burnett Benjamin J., Dinos George, Reynolds Kevin A., Blanchard Scott C., Steitz Thomas A., Wilson Daniel N.. . Distinct tRNA Accommodation Intermediates Observed on the Ribosome with the Antibiotics Hygromycin A and A201A Molecular Cell
5dox Sept. 11, 2015 Polikanov Yury S., Starosta Agata L., Juette Manuel F., Altman Roger B., Terry Daniel S., Lu Wanli, Burnett Benjamin J., Dinos George, Reynolds Kevin A., Blanchard Scott C., Steitz Thomas A., Wilson Daniel N.. . Distinct tRNA Accommodation Intermediates Observed on the Ribosome with the Antibiotics Hygromycin A and A201A Molecular Cell
5doy Sept. 11, 2015 Polikanov Yury S., Starosta Agata L., Juette Manuel F., Altman Roger B., Terry Daniel S., Lu Wanli, Burnett Benjamin J., Dinos George, Reynolds Kevin A., Blanchard Scott C., Steitz Thomas A., Wilson Daniel N.. . Distinct tRNA Accommodation Intermediates Observed on the Ribosome with the Antibiotics Hygromycin A and A201A Molecular Cell
5doy Sept. 11, 2015 Polikanov Yury S., Starosta Agata L., Juette Manuel F., Altman Roger B., Terry Daniel S., Lu Wanli, Burnett Benjamin J., Dinos George, Reynolds Kevin A., Blanchard Scott C., Steitz Thomas A., Wilson Daniel N.. . Distinct tRNA Accommodation Intermediates Observed on the Ribosome with the Antibiotics Hygromycin A and A201A Molecular Cell
8fc1 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
8fc1 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
8fc2 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
8fc2 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
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
8fc4 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
8fc4 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
8fc5 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
8fc5 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

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 511.17 g/mol
HBA 12
HBD 6
HBA + HBD
AlogP -2.91
TPSA 201.31
RB 6

Radar chart