CAS 72877-50-0
:(-)-Neplanocin A
Description:
(-)-Neplanocin A is a naturally occurring nucleoside analog with notable antiviral properties, particularly against certain RNA viruses. It is characterized by its unique structure, which includes a ribonucleoside framework with a specific stereochemistry that imparts its biological activity. The compound is known for its ability to inhibit the enzyme S-adenosylhomocysteine hydrolase, which is crucial in the metabolism of adenosine and related compounds. This inhibition leads to a depletion of intracellular levels of S-adenosylhomocysteine, ultimately affecting viral replication. (-)-Neplanocin A exhibits a relatively low toxicity profile, making it a subject of interest in antiviral research. Its solubility in water and organic solvents varies, which can influence its bioavailability and efficacy in therapeutic applications. The compound has been studied for its potential use in treating viral infections and may also have implications in cancer therapy due to its effects on cellular metabolism. Overall, (-)-Neplanocin A represents a significant compound in medicinal chemistry, particularly in the development of antiviral agents.
Formula:C11H13N5O3
InChI:InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1
InChI key:InChIKey=XUGWUUDOWNZAGW-VDAHYXPESA-N
SMILES:O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)C=C(CO)[C@H]1O
Synonyms:- 3-Cyclopentene-1,2-diol, 5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-, (1S,2R,5R)-
- Neplanocin A
- (1S,2R,5R)-5-(6-Amino-9H-purin-9-yl)-3-(hydroxymethyl)-3-cyclopentene-1,2-diol
- 3-Cyclopentene-1,2-diol, 5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-, [1S-(1α,2α,5β)]-
- (-)-Neplanocin A
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Found 2 products.
(-)-Neplanocin A
CAS:<p>S-Adenosylhomocysteine (SAH) hydrolase is responsible for the reversible hydrolysis of SAH into adenosine and homocysteine. Inhibition of this enzyme leads to the accumulation of SAH within cells, thereby increasing the SAH to S-adenosylmethionine (SAM) ratio and subsequently inhibiting SAM-dependent methyltransferases. (−)-Neplanocin A, a potent and irreversible inhibitor of SAH hydrolase (Ki= 8.39 nM), exhibits significant antitumor activity against mouse leukemia L1210 cells and holds broad-spectrum antiviral properties. Its efficacy notably surpasses that of the reversible inhibitor 3-deazaneplanocin, especially in combating vesicular stomatitis, evidencing a higher potency with ID50 values of 0.07 μg/ml for Neplanocin A versus 0.3 μg/ml for 3-deazaneplanocin.</p>Formula:C11H13N5O3Color and Shape:SolidMolecular weight:263.3
