Cordycepin

Cordycepin
Names
IUPAC name
3′-Deoxyadenosine
Systematic IUPAC name
(2S,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Other names
Cordycepine
9-(3-Deoxy-β-D-ribofuranosyl)adenine
3-dA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.720 Edit this at Wikidata
UNII
  • 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
  • O[C@@H]1C[C@@H](CO)O[C@H]1N2C(N=CN=C3N)=C3N=C2
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N
Properties
C10H13N5O3
Molar mass 251.246 g·mol−1
Melting point 225.5 °C (437.9 °F; 498.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the 3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris,[1] but can now be produced synthetically.[2] It is also found in other Cordyceps species as well as Ophiocordyceps sinensis.[3]

  1. ^ Cunningham, K. G., Manson, W., Spring, F. S., Hutchinson, S. A. (1950). "Cordycepin, a Metabolic Product isolated from Cultures of Cordyceps militaris (Linn.) Link". Nature. 166 (4231): 949. Bibcode:1950Natur.166..949C. doi:10.1038/166949a0. PMID 14796634.
  2. ^ Huang S, Liu H, Sun Y, Chen J, Li X, Xu J, Hu Y, Li Y, Deng Z, Zhong S (2018-01-01). "An effective and convenient synthesis of cordycepin from adenosine". Chemical Papers. 72 (1): 149–160. doi:10.1007/s11696-017-0266-9. ISSN 1336-9075. S2CID 90915876.
  3. ^ Zhou X, Luo L, Dressel W, Shadier G, Krumbiegel D, Schmidtke P, Zepp F, Meyer CU (2008). "Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis". The American Journal of Chinese Medicine. 36 (5): 967–80. doi:10.1142/S0192415X08006387. PMID 19051361.