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Record Information
Version3.6
Creation Date2006-05-22 15:12:30 UTC
Update Date2016-05-16 17:37:43 UTC
HMDB IDHMDB03075
Secondary Accession NumbersNone
Metabolite Identification
Common NameFlavone
DescriptionQuercetin is a flavonoid that forms the "backbone" for many other flavonoids, including the citrus flavonoids rutin, hesperidin, naringin and tangeritin. In studies, quercetin is found to be the most active of the flavonoids, and many medicinal plants owe much of their activity to their high quercetin content. Quercetin has demonstrated significant anti-inflammatory activity because of direct inhibition of several initial processes of inflammation. For example, it inhibits both the manufacture and release of histamine and other allergic/inflammatory mediators. In addition, it exerts potent antioxidant activity and vitamin C-sparing action. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
2-Phenyl-4-benzopyronChEBI
2-Phenyl-4-chromoneChEBI
2-Phenyl-4H-1-benzopyran-4-oneChEBI
2-Phenyl-4H-benzopyran-4-oneChEBI
2-PHENYL-4H-chromen-4-oneChEBI
2-Phenyl-gamma-benzopyroneChEBI
2-Phenylbenzopyran-4-oneChEBI
2-PhenylchromoneChEBI
FlavonChEBI
2-Phenyl-g-benzopyroneGenerator
2-Phenyl-γ-benzopyroneGenerator
Chemical FormulaC15H10O2
Average Molecular Weight222.2387
Monoisotopic Molecular Weight222.068079564
IUPAC Name2-phenyl-4H-chromen-4-one
Traditional Nameflavone
CAS Registry Number525-82-6
SMILES
O=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
InChI KeyInChIKey=VHBFFQKBGNRLFZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • Flavone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point100 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.56HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0082 mg/mLALOGPS
logP3.54ALOGPS
logP2.97ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.63ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.97 m3·mol-1ChemAxon
Polarizability23.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-00dl-8930000000-3944bcd59fd467475fe4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0190000000-c5dc113240ef2eddc9bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0udi-0900000000-cbc602f9fb305cfab2adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-0900000000-1767db1ce89913542708View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-8980000000-8dd4180be084c0205feeView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
  • Placenta
  • Prostate
  • Spleen
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07776
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB006784
KNApSAcK IDC00001040
Chemspider ID10230
KEGG Compound IDC10043
BioCyc IDCPD-8485
BiGG IDNot Available
Wikipedia LinkFlavone
NuGOwiki LinkHMDB03075
Metagene LinkHMDB03075
METLIN ID3359
PubChem Compound10680
PDB IDFLN
ChEBI ID42491
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ching LM, Joseph WR, Crosier KE, Baguley BC: Induction of tumor necrosis factor-alpha messenger RNA in human and murine cells by the flavone acetic acid analogue 5,6-dimethylxanthenone-4-acetic acid (NSC 640488). Cancer Res. 1994 Feb 15;54(4):870-2. [8313372 ]
  2. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [12787887 ]
  3. Cummings J, Kerr DJ, Kaye SB, Smyth JF: Optimisation of a reversed-phase high-performance liquid chromatographic method for the determination of flavone acetic acid and its major human metabolites in plasma and urine. J Chromatogr. 1988 Sep 23;431(1):77-85. [3235538 ]
  4. Choi MH, Kim KR, Hong JK, Park SJ, Chung BC: Determination of non-steroidal estrogens in breast milk, plasma, urine and hair by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(24):2221-8. [12478564 ]
  5. Cai H, Steward WP, Gescher AJ: Determination of the putative cancer chemopreventive flavone tricin in plasma and tissues of mice by HPLC with UV--visible detection. Biomed Chromatogr. 2005 Sep;19(7):518-22. [15828058 ]
  6. Barrellier MT: [Lymphedema: is there a treatment?] Rev Med Interne. 1992 Jan-Feb;13(1):49-57. [1410875 ]
  7. Sengupta B, Uematsu T, Jacobsson P, Swenson J: Exploring the antioxidant property of bioflavonoid quercetin in preventing DNA glycation: a calorimetric and spectroscopic study. Biochem Biophys Res Commun. 2006 Jan 6;339(1):355-61. Epub 2005 Nov 15. [16300739 ]
  8. Weiss RB, Greene RF, Knight RD, Collins JM, Pelosi JJ, Sulkes A, Curt GA: Phase I and clinical pharmacology study of intravenous flavone acetic acid (NSC 347512). Cancer Res. 1988 Oct 15;48(20):5878-82. [3167843 ]
  9. Alonso M, Tamasdan C, Miller DC, Newcomb EW: Flavopiridol induces apoptosis in glioma cell lines independent of retinoblastoma and p53 tumor suppressor pathway alterations by a caspase-independent pathway. Mol Cancer Ther. 2003 Feb;2(2):139-50. [12589031 ]
  10. Kim SJ: Effect of biflavones of Ginkgo biloba against UVB-induced cytotoxicity in vitro. J Dermatol. 2001 Apr;28(4):193-9. [11449670 ]