sakuranetin

Also known as 4',5-dihydroxy-7-methoxyflavanone, 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one, (S)-(-)-4',5-dihydroxy-7-methoxyflavanone, (S)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one

Sakuranetin is a flavan-on, the 7-methoxy derivative of naringenin, found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae. __TOC__ == Glycosides == Sakuranin is the 5-O-glucoside of sakuranetin.

Chemical data

Formula: C16H14O5
Molecular weight: 286.28 g/mol
IUPAC name: (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
SMILES: COC1=CC(=C2C(=O)C[C@H](OC2=C1)C3=CC=C(C=C3)O)O
InChIKey: DJOJDHGQRNZXQQ-AWEZNQCLSA-N
XLogP: 2.7
Polar surface area: 76 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: flavanone
Mass: 286.084

Show 5 more facts

found in taxon: Xanthorrhoea australis
chemical formula: C₁₆H₁₄O₅
canonical SMILES: COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
isomeric SMILES: COC1=CC(=C2C(=O)C[C@H](OC2=C1)C3=CC=C(C=C3)O)O
subject has role: bactericide

Sources (2)

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Encyclopedic overview

3 sections

Contents

Glycosides
Metabolism
References

== Metabolism == biosynthesis Naringenin 7-O-methyltransferase uses naringenin to yield sakuranetin, with S-adenosyl-methionine as the methyl donor. biodegradation In compounds like 7-methoxylated flavanones like sakuranetin, demethylation followed by sulfation occur in model organism Cunninghamella elegans.

Excerpted from Wikipedia’s “sakuranetin” article, available under the CC BY-SA 4.0 licence.

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