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Merck

C3394

Cordycepin

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

Synonym(s):

3′-Deoxyadenosine

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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

Skull and crossbones
GHS06

signalword

Danger

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
0000488199
0000467763
0000467763
0000455818

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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
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
Suman K Vodnala et al.
Journal of medicinal chemistry, 56(24), 9861-9873 (2013-11-29)
Novel methods for treatment of African trypanosomiasis, caused by infection with Trypanosoma brucei are needed. Cordycepin (3'-deoxyadenosine, 1a) is a powerful trypanocidal compound in vitro but is ineffective in vivo because of rapid metabolic degradation by adenosine deaminase (ADA). We
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.
Ying-Yi Chen et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(8-9), 768-778 (2012-04-03)
Cancer metastasis is a primary cause of cancer death. Antrodia cinnamomea (A. cinnamomea), a medicinal mushroom in Taiwan, has been shown antioxidant and anticancer activities. In this study, we first observed that ethanol extract of fruiting bodies of A. cinnamomea
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Product Information Sheet - C3394

Product Information Sheet

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