HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound TAC

Identifiers

  • Canonical SMILES: 
    CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(N)=O)C(=O)c4c(O)cccc4[C@@]3(C)O
  • IUPAC name: 
    (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  • InChi: 
    InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
  • InChiKey: 
    OFVLGDICTFRJMM-WESIUVDSSA-N
  • SMARTS: 
    [#6]-[#7](-[#6])-[#6@H]1-[#6@@H]2-[#6]-[#6@H]3-[#6](=[#6](-[#8])-[#6@]-2(-[#8])-[#6](=[#8])-[#6](=[#6]-1-[#8])-[#6](-[#7])=[#8])-[#6](=[#8])-[#6]1:[#6](-[#8]):[#6]:[#6]:[#6]:[#6]:1-[#6@@]-3(-[#6])-[#8]

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

RNA-SM complexes

PDB code Deposition date Reference publication
1hnw Dec. 8, 2000 Brodersen Ditlev E., Clemons William M., Carter Andrew P., Morgan-Warren Robert J., Wimberly Brian T., Ramakrishnan V.. . The Structural Basis for the Action of the Antibiotics Tetracycline, Pactamycin, and Hygromycin B on the 30S Ribosomal Subunit Cell
1hnw Dec. 8, 2000 Brodersen Ditlev E., Clemons William M., Carter Andrew P., Morgan-Warren Robert J., Wimberly Brian T., Ramakrishnan V.. . The Structural Basis for the Action of the Antibiotics Tetracycline, Pactamycin, and Hygromycin B on the 30S Ribosomal Subunit Cell
1i97 March 18, 2001 Pioletti Marta, Schlünzen Frank, Harms Jörg, Zarivach Raz, Glühmann Marco, Avila Horacio, Bashan Anat, Bartels Heike, Auerbach Tamar, Jacobi Carsten, Hartsch Thomas, Yonath Ada, Franceschi François. . Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3 The EMBO Journal
1i97 March 18, 2001 Pioletti Marta, Schlünzen Frank, Harms Jörg, Zarivach Raz, Glühmann Marco, Avila Horacio, Bashan Anat, Bartels Heike, Auerbach Tamar, Jacobi Carsten, Hartsch Thomas, Yonath Ada, Franceschi François. . Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3 The EMBO Journal
1i97 March 18, 2001 Pioletti Marta, Schlünzen Frank, Harms Jörg, Zarivach Raz, Glühmann Marco, Avila Horacio, Bashan Anat, Bartels Heike, Auerbach Tamar, Jacobi Carsten, Hartsch Thomas, Yonath Ada, Franceschi François. . Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3 The EMBO Journal
1i97 March 18, 2001 Pioletti Marta, Schlünzen Frank, Harms Jörg, Zarivach Raz, Glühmann Marco, Avila Horacio, Bashan Anat, Bartels Heike, Auerbach Tamar, Jacobi Carsten, Hartsch Thomas, Yonath Ada, Franceschi François. . Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3 The EMBO Journal
1i97 March 18, 2001 Pioletti Marta, Schlünzen Frank, Harms Jörg, Zarivach Raz, Glühmann Marco, Avila Horacio, Bashan Anat, Bartels Heike, Auerbach Tamar, Jacobi Carsten, Hartsch Thomas, Yonath Ada, Franceschi François. . Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3 The EMBO Journal
4v9a July 18, 2012 Jenner Lasse, Starosta Agata L., Terry Daniel S., Mikolajka Aleksandra, Filonava Liudmila, Yusupov Marat, Blanchard Scott C., Wilson Daniel N., Yusupova Gulnara. . Structural basis for potent inhibitory activity of the antibiotic tigecycline during protein synthesis Proceedings of the National Academy of Sciences
4v9a July 18, 2012 Jenner Lasse, Starosta Agata L., Terry Daniel S., Mikolajka Aleksandra, Filonava Liudmila, Yusupov Marat, Blanchard Scott C., Wilson Daniel N., Yusupova Gulnara. . Structural basis for potent inhibitory activity of the antibiotic tigecycline during protein synthesis Proceedings of the National Academy of Sciences
5j5b April 1, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
5j5b April 1, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
5j7l April 6, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
5j7l April 6, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
5j7l April 6, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
5j7l April 6, 2016 Cocozaki Alexis I., Altman Roger B., Huang Jian, Buurman Ed T., Kazmirski Steven L., Doig Peter, Prince D. Bryan, Blanchard Scott C., Cate Jamie H. D., Ferguson Andrew D.. . Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors Proceedings of the National Academy of Sciences
8cf1 Feb. 2, 2023 Paternoga Helge, Crowe-McAuliffe Caillan, Bock Lars V., Koller Timm O., Morici Martino, Beckert Bertrand, Myasnikov Alexander G., Grubmüller Helmut, Nováček Jiří, Wilson Daniel N.. . Structural conservation of antibiotic interaction with ribosomes Nature Structural & Molecular Biology
8cgj Feb. 5, 2023 Paternoga Helge, Crowe-McAuliffe Caillan, Bock Lars V., Koller Timm O., Morici Martino, Beckert Bertrand, Myasnikov Alexander G., Grubmüller Helmut, Nováček Jiří, Wilson Daniel N.. . Structural conservation of antibiotic interaction with ribosomes Nature Structural & Molecular Biology
8syk May 25, 2023 Stagno Jason R, Deme Justin C, Dwivedi Vibha, Lee Yun-Tzai, Lee Hyun Kyung, Yu Ping, Chen Szu-Yun, Fan Lixin, Degenhardt Maximilia F S, Chari Raj, Young Howard A, Lea Susan M, Wang Yun-Xing. . Structural investigation of an RNA device that regulates PD-1 expression in mammalian cells Nucleic Acids Research
8syk May 25, 2023 Stagno Jason R, Deme Justin C, Dwivedi Vibha, Lee Yun-Tzai, Lee Hyun Kyung, Yu Ping, Chen Szu-Yun, Fan Lixin, Degenhardt Maximilia F S, Chari Raj, Young Howard A, Lea Susan M, Wang Yun-Xing. . Structural investigation of an RNA device that regulates PD-1 expression in mammalian cells Nucleic Acids Research
8syk May 25, 2023 Stagno Jason R, Deme Justin C, Dwivedi Vibha, Lee Yun-Tzai, Lee Hyun Kyung, Yu Ping, Chen Szu-Yun, Fan Lixin, Degenhardt Maximilia F S, Chari Raj, Young Howard A, Lea Susan M, Wang Yun-Xing. . Structural investigation of an RNA device that regulates PD-1 expression in mammalian cells Nucleic Acids Research
8syk May 25, 2023 Stagno Jason R, Deme Justin C, Dwivedi Vibha, Lee Yun-Tzai, Lee Hyun Kyung, Yu Ping, Chen Szu-Yun, Fan Lixin, Degenhardt Maximilia F S, Chari Raj, Young Howard A, Lea Susan M, Wang Yun-Xing. . Structural investigation of an RNA device that regulates PD-1 expression in mammalian cells Nucleic Acids Research
8t5o June 14, 2023 Stagno Jason R, Deme Justin C, Dwivedi Vibha, Lee Yun-Tzai, Lee Hyun Kyung, Yu Ping, Chen Szu-Yun, Fan Lixin, Degenhardt Maximilia F S, Chari Raj, Young Howard A, Lea Susan M, Wang Yun-Xing. . Structural investigation of an RNA device that regulates PD-1 expression in mammalian cells Nucleic Acids Research

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 444.15 g/mol
HBA 9
HBD 6
HBA + HBD
AlogP -0.21
TPSA 181.62
RB 2

Radar chart