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C3394

Sigma-Aldrich

Cordycepin

from Cordyceps militaris

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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

form

powder

antibiotic activity spectrum

fungi

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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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1 of 4

This Item
G2536S8559A1287
Cordycepin from Cordyceps militaris

Sigma-Aldrich

C3394

Cordycepin

Ganciclovir ≥99% (HPLC), powder

Sigma-Aldrich

G2536

Ganciclovir

Sinefungin 95% (HPLC), powder

Sigma-Aldrich

S8559

Sinefungin

5-Azacytidine Hybri-Max™, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma

Sigma-Aldrich

A1287

5-Azacytidine

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

biological source

Cordyceps militaris

biological source

-

biological source

-

biological source

synthetic (organic)

antibiotic activity spectrum

fungi

antibiotic activity spectrum

viruses

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes

mode of action

DNA synthesis | interferes

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

DNA synthesis | interferes

General description

Chemical structure: nucleoside

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

Certificates of Analysis (COA)

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USP

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Adenosine

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
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
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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
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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