HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound SAH

Identifiers

  • Canonical SMILES: 
    N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O
  • IUPAC name: 
    (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid (non-preferred name)
  • InChi: 
    InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
  • InChiKey: 
    ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

439155 CHEMBL418052 DB01752

RNA-SM complexes

PDB code Deposition date Reference publication
1av6 Sept. 26, 1997 Hodel Alec E., Gershon Paul D., Quiocho Florante A.. . Structural Basis for Sequence-Nonspecific Recognition of 5′-Capped mRNA by a Cap-Modifying Enzyme Molecular Cell
2bh2 Jan. 6, 2005 Lee Tom T., Agarwalla Sanjay, Stroud Robert M.. . A Unique RNA Fold in the RumA-RNA-Cofactor Ternary Complex Contributes to Substrate Selectivity and Enzymatic Function Cell
2bh2 Jan. 6, 2005 Lee Tom T., Agarwalla Sanjay, Stroud Robert M.. . A Unique RNA Fold in the RumA-RNA-Cofactor Ternary Complex Contributes to Substrate Selectivity and Enzymatic Function Cell
3e5e Aug. 13, 2008 Lu Changrui, Smith Angela M, Fuchs Ryan T, Ding Fang, Rajashankar Kanagalaghatta, Henkin Tina M, Ke Ailong. . Crystal structures of the SAM-III/SMK riboswitch reveal the SAM-dependent translation inhibition mechanism Nature Structural & Molecular Biology
3gx3 April 1, 2009 Montange Rebecca K., Mondragón Estefanía, van Tyne Daria, Garst Andrew D., Ceres Pablo, Batey Robert T.. . Discrimination between Closely Related Cellular Metabolites by the SAM-I Riboswitch Journal of Molecular Biology
3htx June 12, 2009 Huang Ying, Ji Lijuan, Huang Qichen, Vassylyev Dmitry G., Chen Xuemei, Ma Jin-Biao. . Structural insights into mechanisms of the small RNA methyltransferase HEN1 Nature
3htx June 12, 2009 Huang Ying, Ji Lijuan, Huang Qichen, Vassylyev Dmitry G., Chen Xuemei, Ma Jin-Biao. . Structural insights into mechanisms of the small RNA methyltransferase HEN1 Nature
3npn June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3npq June 28, 2010 Edwards Andrea L., Reyes Francis E., Héroux Annie, Batey Robert T.. . Structural basis for recognition ofS-adenosylhomocysteine by riboswitches RNA
3pla Nov. 15, 2010 Lin Jinzhong, Lai Shaomei, Jia Ru, Xu Anbi, Zhang Liman, Lu Jing, Ye Keqiong. . Structural basis for site-specific ribose methylation by box C/D RNA protein complexes Nature
3pla Nov. 15, 2010 Lin Jinzhong, Lai Shaomei, Jia Ru, Xu Anbi, Zhang Liman, Lu Jing, Ye Keqiong. . Structural basis for site-specific ribose methylation by box C/D RNA protein complexes Nature
3pla Nov. 15, 2010 Lin Jinzhong, Lai Shaomei, Jia Ru, Xu Anbi, Zhang Liman, Lu Jing, Ye Keqiong. . Structural basis for site-specific ribose methylation by box C/D RNA protein complexes Nature
5cd1 July 2, 2015 Finer-Moore Janet, Czudnochowski Nadine, O'Connell Joseph D., Wang Amy Liya, Stroud Robert M.. . Crystal Structure of the Human tRNA m1A58 Methyltransferase–tRNA3Lys Complex: Refolding of Substrate tRNA Allows Access to the Methylation Target Journal of Molecular Biology
5cd1 July 2, 2015 Finer-Moore Janet, Czudnochowski Nadine, O'Connell Joseph D., Wang Amy Liya, Stroud Robert M.. . Crystal Structure of the Human tRNA m1A58 Methyltransferase–tRNA3Lys Complex: Refolding of Substrate tRNA Allows Access to the Methylation Target Journal of Molecular Biology
5dto Sept. 18, 2015 Zhao Yongqian, Soh Tingjin Sherryl, Lim Siew Pheng, Chung Ka Yan, Swaminathan Kunchithapadam, Vasudevan Subhash G., Shi Pei-Yong, Lescar Julien, Luo Dahai. . Molecular basis for specific viral RNA recognition and 2′-O-ribose methylation by the dengue virus nonstructural protein 5 (NS5) Proceedings of the National Academy of Sciences
5gin June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gin June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gin June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gio June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gio June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gio June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gip June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gip June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gip June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5gip June 24, 2016 Yang Zuxiao, Lin Jinzhong, Ye Keqiong. . Box C/D guide RNAs recognize a maximum of 10 nt of substrates Proceedings of the National Academy of Sciences
5zq0 April 17, 2018 Jiang Yiyang, Yu Hailong, Li Fudong, Cheng Lin, Zhu Lingru, Shi Yunyu, Gong Qingguo. . Unveiling the structural features that determine the dual methyltransferase activities of Streptococcus pneumoniae RlmCD PLOS Pathogens
6hag Aug. 7, 2018 Weickhmann A Katharina, Keller Heiko, Wurm Jan P, Strebitzer Elisabeth, Juen Michael A, Kremser Johannes, Weinberg Zasha, Kreutz Christoph, Duchardt-Ferner Elke, Wöhnert Jens. . The structure of the SAM/SAH-binding riboswitch Nucleic Acids Research
6lau Nov. 13, 2019 Sun Aiai, Gasser Catherina, Li Fudong, Chen Hao, Mair Stefan, Krasheninina Olga, Micura Ronald, Ren Aiming. . SAM-VI riboswitch structure and signature for ligand discrimination Nature Communications
6lau Nov. 13, 2019 Sun Aiai, Gasser Catherina, Li Fudong, Chen Hao, Mair Stefan, Krasheninina Olga, Micura Ronald, Ren Aiming. . SAM-VI riboswitch structure and signature for ligand discrimination Nature Communications
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
6yl5 April 6, 2020 Huang Lin, Liao Ting-Wei, Wang Jia, Ha Taekjip, Lilley David M J. . Crystal structure and ligand-induced folding of the SAM/SAH riboswitch Nucleic Acids Research
7jz0 Sept. 1, 2020 Minasov George, Rosas-Lemus Monica, Shuvalova Ludmilla, Inniss Nicole L., Brunzelle Joseph S., Daczkowski Courtney M., Hoover Paul, Mesecar Andrew D., Satchell Karla J. F.. . Mn 2+ coordinates Cap-0-RNA to align substrates for efficient 2′- O -methyl transfer by SARS-CoV-2 nsp16 []
7jz0 Sept. 1, 2020 Minasov George, Rosas-Lemus Monica, Shuvalova Ludmilla, Inniss Nicole L., Brunzelle Joseph S., Daczkowski Courtney M., Hoover Paul, Mesecar Andrew D., Satchell Karla J. F.. . Mn 2+ coordinates Cap-0-RNA to align substrates for efficient 2′- O -methyl transfer by SARS-CoV-2 nsp16 []
7l6r Dec. 23, 2020 Minasov George, Rosas-Lemus Monica, Shuvalova Ludmilla, Inniss Nicole L., Brunzelle Joseph S., Daczkowski Courtney M., Hoover Paul, Mesecar Andrew D., Satchell Karla J. F.. . Mn 2+ coordinates Cap-0-RNA to align substrates for efficient 2′- O -methyl transfer by SARS-CoV-2 nsp16 Science Signaling
7l6t Dec. 23, 2020 Minasov George, Rosas-Lemus Monica, Shuvalova Ludmilla, Inniss Nicole L., Brunzelle Joseph S., Daczkowski Courtney M., Hoover Paul, Mesecar Andrew D., Satchell Karla J. F.. . Mn 2+ coordinates Cap-0-RNA to align substrates for efficient 2′- O -methyl transfer by SARS-CoV-2 nsp16 Science Signaling
7nac June 21, 2021 Cruz Victor Emmanuel, Sekulski Kamil, Peddada Nagesh, Sailer Carolin, Balasubramanian Sahana, Weirich Christine S., Stengel Florian, Erzberger Jan P.. . Sequence-specific remodeling of a topologically complex RNP substrate by Spb4 Nature Structural & Molecular Biology
7naf June 21, 2021 Cruz Victor Emmanuel, Sekulski Kamil, Peddada Nagesh, Sailer Carolin, Balasubramanian Sahana, Weirich Christine S., Stengel Florian, Erzberger Jan P.. . Sequence-specific remodeling of a topologically complex RNP substrate by Spb4 Nature Structural & Molecular Biology
7xpl May 4, 2022 Wang Jiayin, Yang Zuxiao, Ye Keqiong. . Methylation guide RNAs without box C/D motifs RNA
7xpl May 4, 2022 Wang Jiayin, Yang Zuxiao, Ye Keqiong. . Methylation guide RNAs without box C/D motifs RNA
8oiv March 23, 2023 Skvara Petr, Chalupska Dominika, Klima Martin, Kozic Jan, Silhan Jan, Boura Evzen. . Structural basis for RNA-cap recognition and methylation by the mpox methyltransferase VP39 Antiviral Research
8vuo Jan. 29, 2024 Misra Anurag, Rahisuddin R., Parihar Manish, Arya Shailee, Viswanathan Thiruselvam, Jackson Nathaniel, Qi Shan, Chan Siu-Hong, Harris Reuben S., Martinez-Sobrido Luis, Gupta Yogesh K.. . Structural insights into the assembly and regulation of 2′-O RNA methylation by SARS-CoV-2 nsp16/nsp10 Structure
8vuo Jan. 29, 2024 Misra Anurag, Rahisuddin R., Parihar Manish, Arya Shailee, Viswanathan Thiruselvam, Jackson Nathaniel, Qi Shan, Chan Siu-Hong, Harris Reuben S., Martinez-Sobrido Luis, Gupta Yogesh K.. . Structural insights into the assembly and regulation of 2′-O RNA methylation by SARS-CoV-2 nsp16/nsp10 Structure
8y2o Jan. 26, 2024 Ishiguro Kensuke, Fujimura Atsushi, Shirouzu Mikako. . Structural insights into tRNA recognition of the human FTSJ1-THADA complex Communications Biology
9fn2 June 7, 2024 Chen Hsuan-Ai, Okuda Takumi, Lenz Ann-Kathrin, Scheitl Carolin P. M., Schindelin Hermann, Höbartner Claudia. . Structure and catalytic activity of the SAM-utilizing ribozyme SAMURI Nature Chemical Biology
9fn2 June 7, 2024 Chen Hsuan-Ai, Okuda Takumi, Lenz Ann-Kathrin, Scheitl Carolin P. M., Schindelin Hermann, Höbartner Claudia. . Structure and catalytic activity of the SAM-utilizing ribozyme SAMURI Nature Chemical Biology
9hcg Nov. 8, 2024 Glasgow Ruth I. C., Singh Vivek, Peña-Pérez Lucía, Wilhalm Alissa, Moedas Marco F., Moore David, Rosenberger Florian A., Li Xinping, Atanassov Ilian, Saba Mira, Cipullo Miriam, Rorbach Joanna, Wedell Anna, Freyer Christoph, Amunts Alexey, Wredenberg Anna. . The mitochondrial methylation potential gates mitoribosome assembly Nature Communications
9muj Jan. 14, 2025 Tanouti Yousra, Roovers Martine, Wolff Philippe, Lechner Antony, Van Elder Dany, Feller André, Soin Romuald, Gueydan Cyril, Kruys Véronique, Droogmans Louis, Labar Geoffray. . Structural insight into the novel Thermus thermophilus SPOUT methyltransferase RlmR catalysing Um2552 formation in the 23S rRNA A-loop: a case of convergent evolution Nucleic Acids Research
9p6p June 19, 2025
9p6p June 19, 2025
9z2n Nov. 5, 2025 Canepa Jacob, Ruiz-Arroyo Victor M., Schlamowitz Netanya S., Nam Yunsun. . Substrate selectivity of the human RNA m5C methyltransferase NSUN2 Nature
9z2o Nov. 5, 2025 Canepa Jacob, Ruiz-Arroyo Victor M., Schlamowitz Netanya S., Nam Yunsun. . Substrate selectivity of the human RNA m5C methyltransferase NSUN2 Nature
9z2u Nov. 5, 2025 Canepa Jacob, Ruiz-Arroyo Victor M., Schlamowitz Netanya S., Nam Yunsun. . Substrate selectivity of the human RNA m5C methyltransferase NSUN2 Nature
9z2w Nov. 5, 2025 Canepa Jacob, Ruiz-Arroyo Victor M., Schlamowitz Netanya S., Nam Yunsun. . Substrate selectivity of the human RNA m5C methyltransferase NSUN2 Nature
9z3d Nov. 6, 2025 Canepa Jacob, Ruiz-Arroyo Victor M., Schlamowitz Netanya S., Nam Yunsun. . Substrate selectivity of the human RNA m5C methyltransferase NSUN2 Nature

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 384.41 g/mol
HBA not available
HBD not available
HBA + HBD
AlogP not available
TPSA not available
RB not available

Radar chart