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Merck

C9137

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
NACRES:
NA.51
PubChem Substance ID:
24893135
UNSPSC Code:
41106305
MDL number:
MFCD00057015

Product Name

Cordycepin 5′-triphosphate sodium salt, ≥95%

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);;

SMILES string

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

InChI key

FRGBONDYLMUOMH-UHFFFAOYSA-N

assay

≥95%

form

powder

mol wt

491.18  g/mol

storage temp.

−20°C

Quality Level

200

Related Categories

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.

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000469458
0000469458
0000443030
0000443041
0000443041

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Junhua Pan et al.
Nature, 577(7789), 275-279 (2019-11-08)
Respiratory syncytial virus (RSV) and human metapneumovirus (HMPV) cause severe respiratory diseases in infants and elderly adults1. No vaccine or effective antiviral therapy currently exists to control RSV or HMPV infections. During viral genome replication and transcription, the tetrameric phosphoprotein
Lisa S Chen et al.
British journal of haematology, 140(6), 682-391 (2008-01-22)
Multiple myeloma (MM) is an incurable plasma cell malignancy that is slow-growing, and thus traditional DNA-replication directed chemotherapeutics are ineffective. We hypothesized that those agents that target RNA-directed processes would be successful in MM. To test this postulate, cordycepin, a
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%
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
Nicole Montreau et al.
Comptes rendus biologies, 326(12), 1135-1147 (2004-01-30)
Using an in vivo heterologous system to study the stability of Xenopus laevis RNA injected into axolotl (Ambystoma mexicanum) fertilized eggs, we have previously observed unexpected fluctuations in RNA level during early development [Andéol et al., Differentiation 63 (1998) 69-79].
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