Structure via PubChem · Public domain (PubChem)
cordycepin
Sign in to saveAlso known as 3'-deoxyadenosine, 9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-, Cordycepine, 9-Cordyceposidoadenine, 9-(beta-D-3'-Deoxyribofuranosyl)adenine, COR
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, but can now be produced synthetically.
Chemical data
- Formula
- C10H13N5O3
- Molecular weight
- 251.24 g/mol
- IUPAC name
- (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
- SMILES
- C1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C(N=CN=C32)N)CO
- InChIKey
- OFEZSBMBBKLLBJ-BAJZRUMYSA-N
- XLogP
- -1.2
- Polar surface area
- 119 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 1
- Molecule type
- Small molecule
- Indications
- leukemia
via ChEMBL · EBI
Research
1,634 papers- Cordycepin Modulates Microglial M2 Polarization Coupled with Mitochondrial Metabolic Reprogramming by Targeting HKII and PDK2.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
- Cordycepin and kinase inhibition in cancer.Drug discovery today · 2023
- Cordycepin Ameliorates Nonalcoholic Steatohepatitis by Activation of the AMP-Activated Protein Kinase Signaling Pathway.Hepatology (Baltimore, Md.) · 2021
- Cordycepin: A review of strategies to improve the bioavailability and efficacy.Phytotherapy research : PTR · 2023
- Cordycepin confers long-term neuroprotection via inhibiting neutrophil infiltration and neuroinflammation after traumatic brain injury.Journal of neuroinflammation · 2021
via PubMed
Wikidata facts
- Mass
- 251.102
Show 5 more facts
- chemical formula
- C₁₀H₁₃N₅O₃
- isomeric SMILES
- C1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C2N=CN=C3N)CO
- canonical SMILES
- C1C(OC(C1O)N2C=NC3=C2N=CN=C3N)CO
- subject has role
- antifungal
- Commons category
- Cordycepin
via Wikidata · CC0
~6 min read
Encyclopedic overview
7 sectionsContents
- Occurrence
- Biosynthesis
- Biological activity
- Biotechnology
- Pharmacokinetics
- See also
- References
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, but can now be produced synthetically.
== Occurrence == It is also produced by Cordyceps kyusyuensis (a close relative of C. militaris), but not by other insect pathogenic fungi such as C. bassiana, C. confragosa, C. takaomontana, Isaria fumosorosea, M. robertsii, and M. rileyi.
Excerpted from Wikipedia’s “cordycepin” article, available under the CC BY-SA 4.0 licence.