All Photos(1)

C3394

Sigma-Aldrich

Cordycepin

from Cordyceps militaris

Synonym(s):
3′-Deoxyadenosine
Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
Molecular Weight:
251.24
Beilstein:
35194
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Cordyceps militaris

Quality Level

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum

fungi

storage temp.

−20°C

SMILES string

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

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

InChI key

OFEZSBMBBKLLBJ-BAJZRUMYSA-N

Gene Information

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General description

Chemical structure: nucleoside

Packaging

10, 25, 100 mg in glass bottle

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
Alexander Kondrashov et al.
RNA (New York, N.Y.), 18(12), 2236-2250 (2012-11-03)
Cordycepin (3' deoxyadenosine) has long been used in the study of in vitro assembled polyadenylation complexes, because it terminates the poly(A) tail and arrests the cleavage complex. It is derived from caterpillar fungi, which are highly prized in Chinese traditional...
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...
Amanda L Lloyd et al.
Journal of bacteriology, 191(11), 3469-3481 (2009-03-31)
Uropathogenic Escherichia coli (UPEC) strain CFT073 contains 13 large genomic islands ranging in size from 32 kb to 123 kb. Eleven of these genomic islands were individually deleted from the genome, and nine isogenic mutants were tested for their ability...

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