Cordycepin

Names

[ CAS No. ]:
73-03-0

[ Name ]:
Cordycepin

[Synonym ]:
9H-Purin-6-amine, 9-(3-deoxy-β-D-erythro-pentofuranosyl)-
Adenine cordyceposide
EINECS 200-791-4
9H-Purine, 6-amino-9-(3-deoxy-β-D-ribofuranosyl)-
Adenosine,3-deoxy
Cordycepine
MFCD00037998
Cordycepin
Cordyceps fungus powder
cordycepin crystalline
3'-Deoxyadenosine
adenosine, 3'-deoxy-
(-)-cordycepin
3'-Deoxy-D-adenosine

Biological Activity

[Description]:

Cordycepin, which is a nucleoside derivative isolated from Cordyceps, inhibits IL-1β-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts (RASFs) in a dose-dependent manner.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

Natural Products >> Alkaloid

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[Target]

MMP-1

MMP-3

[In Vitro]

Cordycepin is a potent inhibitor of IL-1β-induced chemokine production and MMP expression and strongly blocks the p38/JNK/AP-1 signalling pathway in RASFs. The effect of Cordycepin on cellular toxicity of RASFs is assessed using MTT assay. Treatment of RASFs with Cordycepin (50 μM or 100 μM) for 24 h does not cause any significant change in cell viability. However, cell viability is slightly decreased when cells are incubated with 100 μM Cordycepin for 48 h[1].

[Cell Assay]

RASFs (2×104 cells/well) are treated with various concentrations of Cordycepin (50 μM or 100 μM). After incubation for 1 h, 12 h and 24 h, cells are washed twice with PBS, MTT (0.5 mg/mL PBS) is added to each well and incubated at 37°C for 30 min. Formazan crystals formed are dissolved by adding DMSO (100 μL/well) and the absorbance is read at 570 nm using a microplate reader[1].

[References]

[1]. Noh EM, et al. Cordycepin inhibits IL-1beta-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts. Rheumatology (Oxford). 2009 Jan;48(1):45-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
627.2±65.0 °C at 760 mmHg

[ Melting Point ]:
225-229ºC

[ Molecular Formula ]:
C₁₀H₁₃N₅O₃

[ Molecular Weight ]:
251.242

[ Flash Point ]:
333.1±34.3 °C

[ Exact Mass ]:
251.101837

[ PSA ]:
119.31000

[ LogP ]:
-0.41

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.863

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7358610

CHEMICAL NAME :: Adenosine, 3'-deoxy-

CAS REGISTRY NUMBER :: 73-03-0

BEILSTEIN REFERENCE NO. :: 0035194

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C10-H13-N5-O3

MOLECULAR WEIGHT :: 251.28

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IZ D- BT5OTJ CQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 80 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 20 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 35,119,1982

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335

[ Precautionary Statements ]:
P261-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R25;R36/37/38

[ Safety Phrases ]:
S26-S45

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
AU7358610

[ HS Code ]:
29349990

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Involvement of autophagy in cordycepin-induced apoptosis in human prostate carcinoma LNCaP cells.

Environ. Toxicol. Pharmacol. 38(1) , 239-50, (2014)

Cordycepin, an active ingredient of the insect fungus Cordyceps spp., shows strong antioxidant and anticancer activities. Several molecular mechanisms have been attributed to its inhibitory effects on...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Anti-HCV activity of the Chinese medicinal fungusCordyceps militaris

Biochem. Biophys. Res. Commun. 447(2) , 341-5, (2014)

• Cordyceps militaris (CM) had a moderate anti-HCV activity for RNA replication. • Cordycepin is a responsible compound for the anti-HCV activity of CM. • CM would be a useful anti-HCV agent in combin...