PRUNETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O5
Molecular Weight	284.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C(=O)C(=CO2)C3=CC=C(O)C=C3)C(O)=C1

InChI

InChIKey=KQMVAGISDHMXJJ-UHFFFAOYSA-N

InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway.	2013-08	23597450
Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones.	2010-12-15	21072799
Isoflavones isolated from red clover (Trifolium pratense) inhibit smooth muscle contraction of the isolated rat prostate gland.	2010-09	20638256
Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum.	2010-08	20534735
Secondary metabolites and antimycobacterial activities from the roots of Ficus nervosa.	2010-07	20658670
Flavonoids activate pregnane x receptor-mediated CYP3A4 gene expression by inhibiting cyclin-dependent kinases in HepG2 liver carcinoma cells.	2010-06-16	20553580
Absorption of red clover isoflavones in human subjects: results from a pilot study.	2010-06	20067656
The influence of bovine milk high or low in isoflavones on hepatic gene expression in mice.	2010	20652050
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009-11-18	20087474
Gas chromatographic-mass spectrometric fragmentation study of phytoestrogens as their trimethylsilyl derivatives: identification in soy milk and wastewater samples.	2009-08-07	19577238
Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones.	2009-06-24	19545173
Disposition of flavonoids via enteric recycling: UDP-glucuronosyltransferase (UGT) 1As deficiency in Gunn rats is compensated by increases in UGT2Bs activities.	2009-06	19264971
Structure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase.	2008-08-14	18613661
Flavonoid-responsive nodY-lacZ expression in three phylogenetically different Bradyrhizobium groups.	2008-05	18449225
[Studies on chemical constituents of Primula sikkmensis].	2008-01	18589747
NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.	2008-01	18098226
Disposition of flavonoids via enteric recycling: enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms.	2007-12-07	18052087
Rapid-resolution HPLC with spectrometric detection for the determination and identification of isoflavones in soy preparations and plant extracts.	2007-12	17899029
Amorphane sesquiterpenes from a marine Streptomyces sp.	2007-02	17315965
Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis.	2007-02	17295184
Cytotoxic constituents from Butea superba Roxb.	2007-01-19	16973318
Disposition of flavonoids via enteric recycling: structural effects and lack of correlations between in vitro and in situ metabolic properties.	2006-11	16882763
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.	2006-08-09	16881680
Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.	2006-02-24	16413562
Dalsympathetin--a new isoflavone gentiobioside from Dalbergia sympathetica (Dennst.).	2006-02	16319013
Disposition of flavonoids via recycling: comparison of intestinal versus hepatic disposition.	2005-12	16120792
Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases.	2005-05-30	16650770
Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model.	2005-02	15455178
Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.	2004-11-15	15476679
Immunoassay for biochanin A.	2004-11	15604024
Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species.	2004-10-29	15508833
Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin.	2004-08-11	15291506
Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection.	2003-10-24	14601839
Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.	2003-07	12814970
Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells.	2003-06-20	12704663
Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry.	2003	12811748
In vitro antioxidant activity of some selected Prunus species in Korea.	2002-12	12510840
A new coumaronochromone from Sophora japonica.	2002-03	11991186
Triflavonoids of Ochna calodendron.	2002-02	11830163
Four new isoflavone triglycosides from Sophora japonica.	2001-08	11520241
Effect of enzyme inhibitors on protein quaternary structure determined by on-line size exclusion chromatography-microelectrospray ionization mass spectrometry.	2001-01	11142365

Patents

Name

Type

Language

PRUNETIN

Common Name

English

4',5-DIHYDROXY-7-METHOXYISOFLAVONE

Preferred Name

English

5-HYDROXY-3-(4-HYDROXYPHENYL)-7-METHOXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

PRUNETIN [MI]

Common Name

English

PRUNUSETIN

Common Name

English

Code System Code Type Description

CHEBI

8600