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30925

Sigma-Aldrich

Cordycepin

≥98.0% (HPLC)

Synonym(s):

3′-Deoxyadenosine

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
73-03-0
Molecular Weight:
251.24
Beilstein:
35194
EC Number:
200-791-4
MDL number:
MFCD00037998
UNSPSC Code:
12352203
PubChem Substance ID:
329753604

Assay

≥98.0% (HPLC)

mp

225-229 °C

antibiotic activity spectrum

fungi

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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

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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.

Other Notes

Starting material for the synthesis of cordycepin triphosphate, an inhibitor of replicative synthesis

replaced by

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R I Gumport et al.
Biochemistry, 15(13), 2804-2809 (1976-06-29)
A structural analogue of ATP, 3'-deoxyadenosine triphosphate (3'-dATP), has been synthesized from cordycepin (3'-deoxyadenosine), characterized, and determined to be an inhibitor of ATP-dependent DNA synthesis in Escherichia coli cells which have been reduced permeable to nucleoside triphosphates by treatment with
Ying-Yi Chen et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(8-9), 768-778 (2012-04-03)
Cancer metastasis is a primary cause of cancer death. Antrodia cinnamomea (A. cinnamomea), a medicinal mushroom in Taiwan, has been shown antioxidant and anticancer activities. In this study, we first observed that ethanol extract of fruiting bodies of A. cinnamomea
Yukako Chiba et al.
Plant & cell physiology, 54(2), 180-194 (2012-12-12)
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
Himal Luitel et al.
Medicina (Kaunas, Lithuania), 56(3) (2020-03-20)
Background and objectives: Pulmonary hypertension (PH) is characterized by the vasoconstriction and abnormally proliferative vascular cells. The available allopathic treatment options for PH are still not able to cure the disease. Alternative medicine is becoming popular and drawing the attention
Suman K Vodnala et al.
Journal of medicinal chemistry, 56(24), 9861-9873 (2013-11-29)
Novel methods for treatment of African trypanosomiasis, caused by infection with Trypanosoma brucei are needed. Cordycepin (3'-deoxyadenosine, 1a) is a powerful trypanocidal compound in vitro but is ineffective in vivo because of rapid metabolic degradation by adenosine deaminase (ADA). We
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