C3394

Cordycepin

Name: Cordycepin
Brand: SIGMA

from Cordyceps militaris, ≥98% (HPLC), powder, adenosine analogue

Synonym(s):

3′-Deoxyadenosine

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All Photos(4)

About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₅O₃

CAS Number:

73-03-0

Molecular Weight:

251.24

NACRES:

NA.77

PubChem Substance ID:

24892611

UNSPSC Code:

12352200

EC Number:

200-791-4

MDL number:

MFCD00037998

Beilstein/REAXYS Number:

35194

Product Name

Cordycepin, from Cordyceps militaris

InChI key

OFEZSBMBBKLLBJ-BAJZRUMYSA-N

InChI

1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)C[C@H]3O

biological source

Cordyceps militaris

form

powder

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

−20°C

Quality Level

200

Gene Information

rat ... Adora1(29290)

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Biochem/physiol Actions

Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide and Gene Regulation research. Discover more featured Cyclic Nucleotide and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Chemical structure: nucleoside

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number

0000488199

0000467763

0000455818

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Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells.

E N Kodama et al.

Biochemical pharmacology, 59(3), 273-281 (1999-12-28)

The nucleoside analogue cordycepin (3'-deoxyadenosine, 3'-dA) is substantially more cytotoxic to terminal deoxynucleotidyl transferase positive (TdT+) leukemic cells than to TdT leukemic cells in vitro in the presence of an adenosine deaminase inhibitor, deoxycoformycin (dCF), and has been considered as

mRNAs containing the histone 3' stem-loop are degraded primarily by decapping mediated by oligouridylation of the 3' end.

Wei Su et al.

RNA (New York, N.Y.), 19(1), 1-16 (2012-11-29)

Metazoan replication-dependent histone mRNAs are only present in S-phase, due partly to changes in their stability. These mRNAs end in a unique stem-loop (SL) that is required for both translation and cell-cycle regulation. Previous studies showed that histone mRNA degradation

Cordycepin (3'-deoxyadenosine) attenuates age-related oxidative stress and ameliorates antioxidant capacity in rats.

Thiyagarajan Ramesh et al.

Experimental gerontology, 47(12), 979-987 (2012-09-25)

Free radical-induced oxidative damage is considered to be the most important consequence of the aging process. The activities and capacities of antioxidant systems of cells decline with increased age, leading to the gradual loss of pro-oxidant/antioxidant balance and resulting in

Changes in mRNA stability associated with cold stress in Arabidopsis cells.

Yukako Chiba et al.

Plant & cell physiology, 54(2), 180-194 (2012-12-12)

Control of mRNA half-life is a powerful strategy to adjust individual mRNA levels to various stress conditions, because the mRNA degradation rate controls not only the steady-state mRNA level but also the transition speed of mRNA levels. Here, we analyzed

A Two-Layered Targeting Mechanism Underlies Nuclear RNA Sorting by the Human Exosome.

Guifen Wu et al.

Cell reports, 30(7), 2387-2401 (2020-02-23)

Degradation of transcripts in human nuclei is primarily facilitated by the RNA exosome. To obtain substrate specificity, the exosome is aided by adaptors; in the nucleoplasm, those adaptors are the nuclear exosome-targeting (NEXT) complex and the poly(A) (pA) exosome-targeting (PAXT) connection.

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