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.

In the Vinony graph

Vinony's link graph records 43 inbound references to sakuranetin, and connects out to digital object identifier, chemical formula and molar mass.

It is catalogued under topics including Aromatase inhibitors, Chembox image size set and ECHA InfoCard ID from Wikidata.

Vinony links it to 9 Wikipedia language editions.

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)

via Wikidata · CC0

~1 min read

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.