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MedKoo Cat#: 466035 | Name: ddhCTP sodium salt

Description:

WARNING: This product is for research use only, not for human or veterinary use.

ddhCTP sodium salt is a novel potent and broad-spectrum antiviral agent, acting as a chain terminator for viral RNA polymerase.

Chemical Structure

ddhCTP sodium salt
ddhCTP sodium salt
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 466035

Name: ddhCTP sodium salt

CAS#: unknown

Chemical Formula: C9H10N3Na4O13P3

Exact Mass: 552.9017

Molecular Weight: 553.07

Elemental Analysis: C, 19.55; H, 1.82; N, 7.60; Na, 16.63; O, 37.61; P, 16.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
2279171-34-3 (free acid) 761971-61-1 (RS-isomer) 2514801-98-8 (racemate) 2657712-17-7 (3triethylamine)
Synonym
ddhCTP sodium salt; ddhCTP sodium;
IUPAC/Chemical Name
sodium ((4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-hydroxy-4,5-dihydrofuran-2-yl)methyl triphosphate
InChi Key
KLFMVASDSPZRQQ-YSPBIQCJSA-J
InChi Code
InChI=1S/C9H14N3O13P3.4Na/c10-7-1-2-12(9(14)11-7)8-6(13)3-5(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17;;;;/h1-3,6,8,13H,4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17);;;;/q;4*+1/p-4/t6-,8-;;;;/m1..../s1
SMILES Code
O=P([O-])(OP([O-])(OP([O-])([O-])=O)=O)OCC1=C[C@@H](O)[C@H](N2C=CC(N)=NC2=O)O1.[Na+].[Na+].[Na+].[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 553.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hsu JC, Laurent-Rolle M, Pawlak JB, Xia H, Kunte A, Hee JS, Lim J, Harris LD, Wood JM, Evans GB, Shi PY, Grove TL, Almo SC, Cresswell P. Viperin triggers ribosome collision-dependent translation inhibition to restrict viral replication. Mol Cell. 2022 Mar 12:S1097-2765(22)00205-2. doi: 10.1016/j.molcel.2022.02.031. Epub ahead of print. PMID: 35316659. 2: Mehta R, Chekmeneva E, Jackson H, Sands C, Mills E, Arancon D, Li HK, Arkell P, Rawson TM, Hammond R, Amran M, Haber A, Cooke GS, Noursadeghi M, Kaforou M, Lewis MR, Takats Z, Sriskandan S. Antiviral metabolite 3'-deoxy-3',4'-didehydro- cytidine is detectable in serum and identifies acute viral infections including COVID-19. Med (N Y). 2022 Mar 11;3(3):204-215.e6. doi: 10.1016/j.medj.2022.01.009. Epub 2022 Jan 31. PMID: 35128501; PMCID: PMC8801973. 3: Passow KT, Caldwell HS, Ngo KA, Arnold JJ, Antczak NM, Narayanan A, Jose J, Sturla SJ, Cameron CE, Ciota AT, Harki DA. A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide. J Med Chem. 2021 Oct 28;64(20):15429-15439. doi: 10.1021/acs.jmedchem.1c01481. Epub 2021 Oct 18. PMID: 34661397; PMCID: PMC8877721. 4: Seifert M, Bera SC, van Nies P, Kirchdoerfer RN, Shannon A, Le TT, Meng X, Xia H, Wood JM, Harris LD, Papini FS, Arnold JJ, Almo S, Grove TL, Shi PY, Xiang Y, Canard B, Depken M, Cameron CE, Dulin D. Inhibition of SARS-CoV-2 polymerase by nucleotide analogs from a single-molecule perspective. Elife. 2021 Oct 7;10:e70968. doi: 10.7554/eLife.70968. PMID: 34617885; PMCID: PMC8497053. 5: Lachowicz JC, Gizzi AS, Almo SC, Grove TL. Structural Insight into the Substrate Scope of Viperin and Viperin-like Enzymes from Three Domains of Life. Biochemistry. 2021 Jul 6;60(26):2116-2129. doi: 10.1021/acs.biochem.0c00958. Epub 2021 Jun 22. PMID: 34156827; PMCID: PMC8672371. 6: Wood JM, Evans GB, Grove TL, Almo SC, Cameron SA, Furneaux RH, Harris LD. Chemical Synthesis of the Antiviral Nucleotide Analogue ddhCTP. J Org Chem. 2021 Jul 2;86(13):8843-8850. doi: 10.1021/acs.joc.1c00761. Epub 2021 Jun 14. PMID: 34126010. 7: Grunkemeyer TJ, Ghosh S, Patel AM, Sajja K, Windak J, Basrur V, Kim Y, Nesvizhskii AI, Kennedy RT, Marsh ENG. The antiviral enzyme viperin inhibits cholesterol biosynthesis. J Biol Chem. 2021 Jul;297(1):100824. doi: 10.1016/j.jbc.2021.100824. Epub 2021 May 23. PMID: 34029588; PMCID: PMC8254119. 8: Seifert M, Bera SC, van Nies P, Kirchdoerfer RN, Shannon A, Le TT, Meng X, Xia H, Wood JM, Harris LD, Papini FS, Arnold JJ, Almo SC, Grove TL, Shi PY, Xiang Y, Canard B, Depken M, Cameron CE, Dulin D. Inhibition of SARS-CoV-2 polymerase by nucleotide analogs: a single molecule perspective. bioRxiv [Preprint]. 2021 Apr 8:2020.08.06.240325. doi: 10.1101/2020.08.06.240325. Update in: Elife. 2021 Oct 07;10: PMID: 33851161; PMCID: PMC8043451. 9: Patel AM, Marsh ENG. The Antiviral Enzyme, Viperin, Activates Protein Ubiquitination by the E3 Ubiquitin Ligase, TRAF6. J Am Chem Soc. 2021 Apr 7;143(13):4910-4914. doi: 10.1021/jacs.1c01045. Epub 2021 Mar 29. PMID: 33779167. 10: Bernheim A, Millman A, Ofir G, Meitav G, Avraham C, Shomar H, Rosenberg MM, Tal N, Melamed S, Amitai G, Sorek R. Prokaryotic viperins produce diverse antiviral molecules. Nature. 2021 Jan;589(7840):120-124. doi: 10.1038/s41586-020-2762-2. Epub 2020 Sep 16. PMID: 32937646; PMCID: PMC7610908. 11: Rivera-Serrano EE, Gizzi AS, Arnold JJ, Grove TL, Almo SC, Cameron CE. Viperin Reveals Its True Function. Annu Rev Virol. 2020 Sep 29;7(1):421-446. doi: 10.1146/annurev-virology-011720-095930. Epub 2020 Jun 30. PMID: 32603630; PMCID: PMC8191541. 12: Ghosh S, Marsh ENG. Viperin: An ancient radical SAM enzyme finds its place in modern cellular metabolism and innate immunity. J Biol Chem. 2020 Aug 14;295(33):11513-11528. doi: 10.1074/jbc.REV120.012784. Epub 2020 Jun 16. PMID: 32546482; PMCID: PMC7450102. 13: Honarmand Ebrahimi K, Vowles J, Browne C, McCullagh J, James WS. ddhCTP produced by the radical-SAM activity of RSAD2 (viperin) inhibits the NAD+ -dependent activity of enzymes to modulate metabolism. FEBS Lett. 2020 May;594(10):1631-1644. doi: 10.1002/1873-3468.13778. Epub 2020 Apr 20. PMID: 32232843. 14: Ebrahimi KH, Howie D, Rowbotham JS, McCullagh J, Armstrong FA, James WS. Viperin, through its radical-SAM activity, depletes cellular nucleotide pools and interferes with mitochondrial metabolism to inhibit viral replication. FEBS Lett. 2020 May;594(10):1624-1630. doi: 10.1002/1873-3468.13761. Epub 2020 Mar 2. PMID: 32061099. 15: Dumbrepatil AB, Zegalia KA, Sajja K, Kennedy RT, Marsh ENG. Targeting viperin to the mitochondrion inhibits the thiolase activity of the trifunctional enzyme complex. J Biol Chem. 2020 Feb 28;295(9):2839-2849. doi: 10.1074/jbc.RA119.011526. Epub 2020 Jan 24. PMID: 31980458; PMCID: PMC7049979. 16: Ghosh S, Patel AM, Grunkemeyer TJ, Dumbrepatil AB, Zegalia K, Kennedy RT, Marsh ENG. Interactions between Viperin, Vesicle-Associated Membrane Protein A, and Hepatitis C Virus Protein NS5A Modulate Viperin Activity and NS5A Degradation. Biochemistry. 2020 Feb 18;59(6):780-789. doi: 10.1021/acs.biochem.9b01090. Epub 2020 Jan 30. PMID: 31977203.

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