Structure via PubChem · Public domain (PubChem)
prunetin
Sign in to saveAlso known as 4',5-dihydroxy-7-methoxyisoflavone, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one, 4',5-dihydroxy-7-methoxygenistein, 7-O-methyl-genistein, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 5,4'-dihydroxy-7-methoxyisoflavone, padmakastein
Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata (the Oregon cherry). Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores. It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.
Chemical data
- Formula
- C16H12O5
- Molecular weight
- 284.26 g/mol
- IUPAC name
- 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
- SMILES
- COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O
- InChIKey
- KQMVAGISDHMXJJ-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 76 Ų
- 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
- isoflavone
- Mass
- 284.068473
Show 5 more facts
- chemical formula
- C₁₆H₁₂O₅
- canonical SMILES
- COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O
- has characteristic
- bitterness
- physically interacts with
- Aldehyde dehydrogenase 2 family member
- Commons category
- Prunetin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Glycosides
- See also
- References
Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata (the Oregon cherry). Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores. It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.
Prunetin can lower blood pressure of spontaneously hypertensive rats and relax isolated rat aortic rings through calcium channel block mechanisms in vessel smooth muscles.
Excerpted from Wikipedia’s “prunetin” article, available under the CC BY-SA 4.0 licence.