HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound ARG

Identifiers

  • Canonical SMILES: 
    N[C@@H](CCCNC(N)=[NH2+])C(O)=O
  • IUPAC name: 
    amino{[(4S)-4-amino-4-carboxybutyl]amino}methaniminium
  • InChi: 
    InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p+1/t4-/m0/s1
  • InChiKey: 
    ODKSFYDXXFIFQN-BYPYZUCNSA-O

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

59294017 DB00125

RNA-SM complexes

PDB code Deposition date Reference publication
1aju May 10, 1997 Brodsky Alexander S, Williamson James R. . Solution structure of the HIV-2 TAR-argininamide complex Journal of Molecular Biology
1akx May 27, 1997 Brodsky Alexander S, Williamson James R. . Solution structure of the HIV-2 TAR-argininamide complex Journal of Molecular Biology
1arj Aug. 30, 1995 Aboul-ela Fareed, Karn Jonathan, Varani Gabriele. . The Structure of the Human Immunodeficiency Virus Type-1 TAR RNA Reveals Principles of RNA Recognition by Tat Protein Journal of Molecular Biology
1koc March 28, 1996 Yang Yinshan, Kochoyan Michel, Burgstaller Petra, Westhof Eric, Famulok Michael. . Structural Basis of Ligand Discrimination by Two Related RNA Aptamers Resolved by NMR Spectroscopy Science
2kx8 April 27, 2010 Durney Michael A., D'Souza Victoria M.. . Preformed Protein-binding Motifs in 7SK snRNA: Structural and Thermodynamic Comparisons with Retroviral TAR Journal of Molecular Biology
2l8h Jan. 12, 2011 Davidson Amy, Begley Darren W., Lau Carmen, Varani Gabriele. . A Small-Molecule Probe Induces a Conformation in HIV TAR RNA Capable of Binding Drug-Like Fragments Journal of Molecular Biology
4y4o Feb. 10, 2015 Polikanov Yury S, Melnikov Sergey V, Söll Dieter, Steitz Thomas A. . Structural insights into the role of rRNA modifications in protein synthesis and ribosome assembly Nature Structural & Molecular Biology
4y4o Feb. 10, 2015 Polikanov Yury S, Melnikov Sergey V, Söll Dieter, Steitz Thomas A. . Structural insights into the role of rRNA modifications in protein synthesis and ribosome assembly Nature Structural & Molecular Biology
4zer April 20, 2015 Seefeldt A Carolin, Nguyen Fabian, Antunes Stéphanie, Pérébaskine Natacha, Graf Michael, Arenz Stefan, Inampudi K Kishore, Douat Céline, Guichard Gilles, Wilson Daniel N, Innis C Axel. . The proline-rich antimicrobial peptide Onc112 inhibits translation by blocking and destabilizing the initiation complex Nature Structural & Molecular Biology
5v8i March 22, 2017
5v8i March 22, 2017
6cfk Feb. 15, 2018 Tereshchenkov Andrey G., Dobosz-Bartoszek Malgorzata, Osterman Ilya A., Marks James, Sergeeva Vasilina A., Kasatsky Pavel, Komarova Ekaterina S., Stavrianidi Andrey N., Rodin Igor A., Konevega Andrey L., Sergiev Petr V., Sumbatyan Natalia V., Mankin Alexander S., Bogdanov Alexey A., Polikanov Yury S.. . Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome Journal of Molecular Biology
6cfk Feb. 15, 2018 Tereshchenkov Andrey G., Dobosz-Bartoszek Malgorzata, Osterman Ilya A., Marks James, Sergeeva Vasilina A., Kasatsky Pavel, Komarova Ekaterina S., Stavrianidi Andrey N., Rodin Igor A., Konevega Andrey L., Sergiev Petr V., Sumbatyan Natalia V., Mankin Alexander S., Bogdanov Alexey A., Polikanov Yury S.. . Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome Journal of Molecular Biology
6cfl Feb. 15, 2018 Tereshchenkov Andrey G., Dobosz-Bartoszek Malgorzata, Osterman Ilya A., Marks James, Sergeeva Vasilina A., Kasatsky Pavel, Komarova Ekaterina S., Stavrianidi Andrey N., Rodin Igor A., Konevega Andrey L., Sergiev Petr V., Sumbatyan Natalia V., Mankin Alexander S., Bogdanov Alexey A., Polikanov Yury S.. . Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome Journal of Molecular Biology
6cfl Feb. 15, 2018 Tereshchenkov Andrey G., Dobosz-Bartoszek Malgorzata, Osterman Ilya A., Marks James, Sergeeva Vasilina A., Kasatsky Pavel, Komarova Ekaterina S., Stavrianidi Andrey N., Rodin Igor A., Konevega Andrey L., Sergiev Petr V., Sumbatyan Natalia V., Mankin Alexander S., Bogdanov Alexey A., Polikanov Yury S.. . Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome Journal of Molecular Biology
6czr April 9, 2018 Serrano Catherine M., Kanna Reddy Hariprasada Reddy, Eiler Daniel, Koch Michael, Tresco Ben I. C., Barrows Louis R., VanderLinden Ryan T., Testa Charles A., Sebahar Paul R., Looper Ryan E.. . Unifying the Aminohexopyranose‐ and Peptidyl‐Nucleoside Antibiotics: Implications for Antibiotic Design Angewandte Chemie
6czr April 9, 2018 Serrano Catherine M., Kanna Reddy Hariprasada Reddy, Eiler Daniel, Koch Michael, Tresco Ben I. C., Barrows Louis R., VanderLinden Ryan T., Testa Charles A., Sebahar Paul R., Looper Ryan E.. . Unifying the Aminohexopyranose‐ and Peptidyl‐Nucleoside Antibiotics: Implications for Antibiotic Design Angewandte Chemie
6xhx 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
6xhx 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
7md7 April 3, 2021 Chen Chih-Wei, Pavlova Julia A., Lukianov Dmitrii A., Tereshchenkov Andrey G., Makarov Gennady I., Khairullina Zimfira Z., Tashlitsky Vadim N., Paleskava Alena, Konevega Andrey L., Bogdanov Alexey A., Osterman Ilya A., Sumbatyan Natalia V., Polikanov Yury S.. . Binding and Action of Triphenylphosphonium Analog of Chloramphenicol upon the Bacterial Ribosome Antibiotics
7md7 April 3, 2021 Chen Chih-Wei, Pavlova Julia A., Lukianov Dmitrii A., Tereshchenkov Andrey G., Makarov Gennady I., Khairullina Zimfira Z., Tashlitsky Vadim N., Paleskava Alena, Konevega Andrey L., Bogdanov Alexey A., Osterman Ilya A., Sumbatyan Natalia V., Polikanov Yury S.. . Binding and Action of Triphenylphosphonium Analog of Chloramphenicol upon the Bacterial Ribosome Antibiotics
7rqa Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqa Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqb Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqb Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqc Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqc Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqd Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqd Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqe Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
7rqe Aug. 6, 2021 Syroegin Egor A., Flemmich Laurin, Klepacki Dorota, Vazquez-Laslop Nora, Micura Ronald, Polikanov Yury S.. . Structural basis for the context-specific action of the classic peptidyl transferase inhibitor chloramphenicol Nature Structural & Molecular Biology
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
8t8b June 22, 2023 Thaler Julia, Syroegin Egor A., Breuker Kathrin, Polikanov Yury S., Micura Ronald. . Practical Synthesis of N-Formylmethionylated Peptidyl-tRNA Mimics ACS Chemical Biology
8t8b June 22, 2023 Thaler Julia, Syroegin Egor A., Breuker Kathrin, Polikanov Yury S., Micura Ronald. . Practical Synthesis of N-Formylmethionylated Peptidyl-tRNA Mimics ACS Chemical Biology
8t8c June 22, 2023 Thaler Julia, Syroegin Egor A., Breuker Kathrin, Polikanov Yury S., Micura Ronald. . Practical Synthesis of N-Formylmethionylated Peptidyl-tRNA Mimics ACS Chemical Biology
8t8c June 22, 2023 Thaler Julia, Syroegin Egor A., Breuker Kathrin, Polikanov Yury S., Micura Ronald. . Practical Synthesis of N-Formylmethionylated Peptidyl-tRNA Mimics ACS Chemical Biology
8vtw Jan. 27, 2024 Aleksandrova Elena V., Ma Cong-Xuan, Klepacki Dorota, Alizadeh Faezeh, Vázquez-Laslop Nora, Liang Jian-Hua, Polikanov Yury S., Mankin Alexander S.. . Macrolones target bacterial ribosomes and DNA gyrase and can evade resistance mechanisms Nature Chemical Biology
8vtw Jan. 27, 2024 Aleksandrova Elena V., Ma Cong-Xuan, Klepacki Dorota, Alizadeh Faezeh, Vázquez-Laslop Nora, Liang Jian-Hua, Polikanov Yury S., Mankin Alexander S.. . Macrolones target bacterial ribosomes and DNA gyrase and can evade resistance mechanisms Nature Chemical Biology
8vty Jan. 27, 2024 Aleksandrova Elena V., Ma Cong-Xuan, Klepacki Dorota, Alizadeh Faezeh, Vázquez-Laslop Nora, Liang Jian-Hua, Polikanov Yury S., Mankin Alexander S.. . Macrolones target bacterial ribosomes and DNA gyrase and can evade resistance mechanisms Nature Chemical Biology
8vty Jan. 27, 2024 Aleksandrova Elena V., Ma Cong-Xuan, Klepacki Dorota, Alizadeh Faezeh, Vázquez-Laslop Nora, Liang Jian-Hua, Polikanov Yury S., Mankin Alexander S.. . Macrolones target bacterial ribosomes and DNA gyrase and can evade resistance mechanisms Nature Chemical Biology
9dfe Aug. 29, 2024 Wright Gerard, Jangra Manoj, Travin Dmitrii, Aleksandrova Elena, Kaur Manpreet, Darwish Lena, Koteva Kalinka, Klepacki Dorota, Wang Wenliang, Tiffany Maya, Sokaribo Akosiererem, Coombes Brian, Vázquez-Laslop Nora, Polikanov Yury, Mankin Alexander. . A Broad Spectrum Lasso Peptide Antibiotic Targeting the Bacterial Ribosome []

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 175.21 g/mol
HBA not available
HBD not available
HBA + HBD
AlogP not available
TPSA not available
RB not available

Radar chart