N4-Hydroxycytidine monophosphate – CAS 4988-54-9

N4-Hydroxycytidine monophosphate – CAS 4988-54-9 is synthesized by Sigut Labs (Prague, Czech Republic). 

Purity (LC-MS)

98%+

Package contents

N4-Hydroxycytidine monophosphate triethylammonium salt

This compound is for research use only. We do not sell to patients.

Amount
1 mg
€ 400

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5 mg
€ 750

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Amount
1 mg
€ 400

Stock

5 mg
€ 750

Stock

Do you want custom amount?
Custom amount

Characterisation

CAS: 4988-54-9
IUPAC name: [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
Other names: N4-OH-CMP, N-Hydroxycytidine 5′-(Dihydrogen Phosphate), Molnupiravir monophosphate
Molecular weight: 339.20 g/mol
Molecular formula: C9H14N3O9P
InChI: InChI=1S/C9H14N3O9P/c13-6-4(3-20-22(17,18)19)21-8(7(6)14)12-2-1-5(11-16)10-9(12)15/h1-2,4,6-8,13-14,16H,3H2,(H,10,11,15)(H2,17,18,19)/t4-,6-,7-,8-/m1/s1

Description

N4-Hydroxycytidine monophosphate– CAS 4988-54-9 is a metabolite of molnupiravir. The 5′-O-triphosphate (β-DN4-4-Hydroxycytidine 5′-triphosphate, EIDD-1931 5′-triphosphate or NHC-TP) is incorporated into the nascent viral RNA by RNA polymerase, causing mutations and the consequent extinction of the virus. This effect is generally called lethal mutagenesis. Molnupiravir can change its structure by tautomerism between a uridine-like form and a cytidine-like form and thus disguise itself from the virus, providing an advantage over other antiviral agents to which some viruses can develop resistance over time.

You can read more about Molnupiravir in our article.

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References

  • Hernandez-Santiago, B. I., Beltran, T., Stuyver, L., Chu, C. K., & Schinazi, R. F. (2004). Metabolism of the anti-hepatitis C virus nucleoside β-d-N 4-hydroxycytidine in different liver cells. Antimicrobial agents and chemotherapy48(12), 4636-4642.
  • Urakova, N., Kuznetsova, V., Crossman, D. K., Sokratian, A., Guthrie, D. B., Kolykhalov, A. A., … & Frolov, I. (2018). β-d-N 4-Hydroxycytidine is a potent anti-alphavirus compound that induces a high level of mutations in the viral genome. Journal of virology92(3), 10-1128.
  • Zhou, S., Hill, C. S., Sarkar, S., Tse, L. V., Woodburn, B. M., Schinazi, R. F., … & Swanstrom, R. (2021). β-D-N 4-hydroxycytidine inhibits SARS-CoV-2 through lethal mutagenesis but is also mutagenic to mammalian cells. The Journal of infectious diseases224(3), 415-419.
  • Agostini, M. L., Pruijssers, A. J., Chappell, J. D., Gribble, J., Lu, X., Andres, E. L., … & Denison, M. R. (2019). Small-molecule antiviral β-d-N 4-hydroxycytidine inhibits a proofreading-intact coronavirus with a high genetic barrier to resistance. Journal of virology93(24), 10-1128.
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