Cordycepin

Cordycepin
IUPAC name 9-(3-Deoxy-β-D-ribofuranosyl)adenine
Other names Cordycepine 3'-Deoxyadenosine
Identifiers
CAS number	73-03-3 Y
PubChem	6303
ChemSpider	6064 N
ChEMBL	CHEMBL305686 N
Jmol-3D images	Image 1
SMILES n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N
InChI 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 N Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N N
Properties
Molecular formula	C10H13N5O3
Molar mass	251.24 g/mol
Melting point	225.5 °C, 499 K, 438 °F
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the absence of oxygen in the 3' position of its ribose part. It was initially extracted from fungi of genus Cordyceps, but is now produced synthetically.

Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two. Therefore, it can participate in certain biochemical reactions (for example, be incorporated into an RNA molecule, thus causing the premature termination of its synthesis).^[1]

It also has interesting properties as an anti-tumor, anti-fungal, anti-viral agent, since it has the ability to inhibit some protein kinases. As an anti-tumor agent, researchers stated that it has the capacity to reduce the growth of ascites tumor cells in the Ehrlich mice with cervical cell carcinoma and Lewis lung cancer.^[2]

See also

• Deoxyadenosine

References

1. ^ Siev, M., Weinberg, R. and Penman, S. (1969). "The selective interruption of nucleolar RNA synthesis in HeLa cells by cordycepin". J. Cell Biol. 41 (2): 510–520. doi:10.1083/jcb.41.2.510. PMC 2107749. PMID 5783871. http://www.jcb.org/cgi/reprint/41/2/510. 
2. ^ Y.J. Ahn, S.J. Park, S.G. Lee, S.C. Shin, D.H. Choi (2000). "Cordycepin: Selective growth inhibitor derived from liquid culture of Cordyceps militaris against Clostridium spp.". J. Agric. Food Chem. 48: 2744–2748. doi:10.1021/jf990862n. PMID 10898616.