5-Hydroxymethyltubercidin
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| Category | Antibiotics |
| Catalog number | BBF-01013 |
| CAS | 49558-38-5 |
| Molecular Weight | 296.28 |
| Molecular Formula | C12H16N4O5 |
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Description
5-Hydroxymethyltubercidin is a semi-synthetic antibiotic made from tuberculin-5-carboxylic acid.
Specification
| Synonyms | 5-(hydroxymethyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine |
| IUPAC Name | 2-[4-amino-5-(hydroxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol |
| Canonical SMILES | C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)CO |
| InChI | InChI=1S/C12H16N4O5/c13-10-7-5(2-17)1-16(11(7)15-4-14-10)12-9(20)8(19)6(3-18)21-12/h1,4,6,8-9,12,17-20H,2-3H2,(H2,13,14,15) |
| InChI Key | HVMYWBSUWVFUFB-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 725.9°C at 760 mmHg |
| Melting Point | 229-230°C |
| Density | 1.93 g/cm3 |
Reference Reading
1. 5-Hydroxymethyltubercidin exhibits potent antiviral activity against flaviviruses and coronaviruses, including SARS-CoV-2
Kentaro Uemura, Haruaki Nobori, Akihiko Sato, Takao Sanaki, Shinsuke Toba, Michihito Sasaki, Akiho Murai, Noriko Saito-Tarashima, Noriaki Minakawa, Yasuko Orba, Hiroaki Kariwa, William W Hall, Hirofumi Sawa, Akira Matsuda, Katsumi Maenaka iScience. 2021 Oct 22;24(10):103120. doi: 10.1016/j.isci.2021.103120. Epub 2021 Sep 11.
Newly emerging or re-emerging viral infections continue to cause significant morbidity and mortality every year worldwide, resulting in serious effects on both health and the global economy. Despite significant drug discovery research against dengue viruses (DENVs) and severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2), no fully effective and specific drugs directed against these viruses have been discovered. Here, we examined the anti-DENV activity of tubercidin derivatives from a compound library from Hokkaido University and demonstrated that 5-hydroxymethyltubercidin (HMTU, HUP1108) possessed both potent anti-flavivirus and anti-coronavirus activities at submicromolar levels without significant cytotoxicity. Furthermore, HMTU inhibited viral RNA replication and specifically inhibited replication at the late stages of the SARS-CoV-2 infection process. Finally, we demonstrated that HMTU 5'-triphosphate inhibited RNA extension catalyzed by the viral RNA-dependent RNA polymerase. Our findings suggest that HMTU has the potential of serving as a lead compound for the development of a broad spectrum of antiviral agents, including SARS-CoV-2.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
