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Merck
CN

C9137

Sigma-Aldrich

Cordycepin 5′-triphosphate sodium salt

≥95%

Synonym(s):

3′-dATP, 3′-deoxy-ATP, 3′-Deoxyadenosine 5′-triphosphate

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About This Item

Empirical Formula (Hill Notation):
C10H16N5O12P3
CAS Number:
71997-32-5
Molecular Weight:
491.18
MDL number:
MFCD00057015
UNSPSC Code:
41106305
PubChem Substance ID:
24893135
NACRES:
NA.51

Key Documents

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Assay

≥95%

form

powder

mol wt

491.18  g/mol

storage temp.

−20°C

SMILES string

[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC3O

InChI

1S/C10H16N5O12P3.Na.H/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(16)1-5(25-10)2-24-29(20,21)27-30(22,23)26-28(17,18)19;;/h3-6,10,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19);;

InChI key

FRGBONDYLMUOMH-UHFFFAOYSA-N

Related Categories

General description

Cordycepin (3′-deoxyadenosine) is a cytotoxic adenosine analog and a bioactive agent extracted from Cordyceps militaris. Cordycepin 5′-triphosphate is a toxic derivative of cordycepin.

Application

Cordycepin 5′-triphosphate sodium salt has been used:
  • as a transcriptional inhibitor in RNA decay assay
  • to inhibit polyadenylation in HEK293T cells before harvesting for in- vitro interaction studies through co-immunoprecipitation (co-Ips)
  • as a positive control in in vitro assays for polymerase inhibition
  • as a precursor to produce cordycepin monophosphate

Biochem/physiol Actions

Cordycepin 5′-triphosphate is incorporated into nucleic acid by poly(A) polymerase. Because it lacks a 3′-hydroxyl group chain production it can be used for 3′-end labeling of RNA.
Cordycepin exhibits various metabolic effects by activating AMP-activated protein kinase (AMPK) in humans. Cordycepin triphosphate inhibits picornavirus polymerase-specific RNA synthesis by blocking in vitro [3H]GMP incorporation. It also retards cell growth by inhibiting RNA synthesis.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000469458
0000469458
0000443030
0000443041
0000443041

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Sandra Holbein et al.
RNA (New York, N.Y.), 15(5), 837-849 (2009-03-28)
Cordycepin (3' deoxyadenosine) is a biologically active compound that, when incorporated during RNA synthesis in vitro, provokes chain termination due to the absence of a 3' hydroxyl moiety. We were interested in the effects mediated by this drug in vivo
Use of vaccinia virus poly(A) polymerase for RNA 3′-end labeling with a chain-terminating nucleotide or a short 3′ homopolymer tract.
Thomson JG, Gershon PD.
Biotechniques, 19, 422-425 (1995)
K Ghoshal et al.
Nucleic acids research, 19(21), 5871-5875 (1991-11-11)
Previous studies have demonstrated that Ara-ATP can inhibit poly(A) polymerase activity by competing with ATP. To elucidate the mechanism of action of this compound, its effect on the cleavage and polyadenylation of two specific substrates, SV40L and adenovirus L3 pre-mRNAs
Vasiliki Daikopoulou et al.
Molecules (Basel, Switzerland), 26(11) (2021-07-03)
Despite the fact that COVID-19 vaccines are already available on the market, there have not been any effective FDA-approved drugs to treat this disease. There are several already known drugs that through drug repositioning have shown an inhibitory activity against
G Costanzo et al.
Molecular and cellular biology, 21(9), 3166-3178 (2001-04-05)
Quantitative analysis of multiple-hit potassium permanganate (KMnO(4)) footprinting has been carried out in vivo on Saccharomyces cerevisiae 5S rRNA genes. The results fix the number of open complexes at steady state in exponentially growing cells at between 8 and 17%
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