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A5762

Adenine 9-β-D-arabinofuranoside

≥99%

Synonym(s):

9-β-D-Arabinofuranosyladenine, Ara-A, Vidarabine

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
5536-17-4
Molecular Weight:
267.24
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
24891019
EC Number:
226-893-9
Beilstein/REAXYS Number:
624881
MDL number:
MFCD00065471
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Quality Segment

100

assay

≥99%

form

powder

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1

InChI key

OIRDTQYFTABQOQ-UHTZMRCNSA-N

Gene Information

mouse ... Ahcy(269378)

General description

Adenine 9-β-D-arabinofuranoside (AraA) is a nucleoside analog. It is an antiviral drug and targets viral DNA polymerases and is majorly used for treating herpes simplex viral infection. It is a potent inhibitor of AMP-activated protein kinase (AMPK). It also inhibits cardiac type 5 adenylyl cyclase but does not improve pathology in cardiovascular diseases.

Application

Adenine 9-β-D-arabinofuranoside has been used for the inhibition of 5′ AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2.
Used to study the roles of AMP-activated protein kinase (AMPK) in cell signaling.

Biochem/physiol Actions

Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV), by inhibition of DNA polymerase.
Cell-permeable adenylyl cyclase inhibitor. IC50 = 30 μM in detergent-dispersed rat brain preparation.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

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