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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003075
Secondary Accession Numbers
  • HMDB03075
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
Data?1582752262
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
Flavone, 14C-labeledMeSH
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 KeyVHBFFQKBGNRLFZ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point100 °CNot Available
Boiling Point367.00 to 368.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility30.52 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.56HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos146.66430932474
[M+H]+Not Available146.798http://allccs.zhulab.cn/database/detail?ID=AllCCS00000544
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0082 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.97 m³·mol⁻¹ChemAxon
Polarizability23.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.05331661259
DarkChem[M-H]-152.83631661259
DeepCCS[M-2H]-181.65830932474
DeepCCS[M+Na]+156.8730932474
AllCCS[M+H]+148.932859911
AllCCS[M+H-H2O]+144.532859911
AllCCS[M+NH4]+153.032859911
AllCCS[M+Na]+154.232859911
AllCCS[M-H]-150.732859911
AllCCS[M+Na-2H]-149.932859911
AllCCS[M+HCOO]-149.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlavoneO=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C13074.9Standard polar33892256
FlavoneO=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C12137.7Standard non polar33892256
FlavoneO=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C12218.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Flavone GC-MS (Non-derivatized)splash10-00dl-8930000000-3944bcd59fd467475fe42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Flavone GC-MS (Non-derivatized)splash10-00dl-8930000000-3944bcd59fd467475fe42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Flavone GC-EI-TOF (Non-derivatized)splash10-00dl-6930000000-af643d33c8bd90e12e342017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkc-0920000000-128b7f1f2509ae8deed12017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-8980000000-8dd4180be084c0205fee2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-00di-0190000000-c5dc113240ef2eddc9bc2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0udi-0900000000-cbc602f9fb305cfab2ad2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0udi-0900000000-1767db1ce899135427082012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Linear Ion Trap , negative-QTOFsplash10-0002-9610000000-8f6ea890ee174ff2cab92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Linear Ion Trap , positive-QTOFsplash10-00fr-0910000000-f99e5ea29982d8657bf32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Linear Ion Trap , positive-QTOFsplash10-03di-0390000000-1a1ab6620996a9ddc4292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone Linear Ion Trap , positive-QTOFsplash10-00di-0090000000-e8ad16adbd7e6c8dcc232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone , positive-QTOFsplash10-00di-0950000000-94425655598eb5a5cfb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone , positive-QTOFsplash10-00di-0090000000-dd86946c50229a30d1242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone , positive-QTOFsplash10-00di-0490000000-5a3c393a8cf2ea0eac182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone LC-ESI-QFT , positive-QTOFsplash10-00di-0090000000-fbeb1951905acd75fd952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 30V, Positive-QTOFsplash10-00fr-2930000000-10590084c5f1e791fcea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 10V, Positive-QTOFsplash10-00di-0090000000-a8f0e8dcf4a988dbb0242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 50V, Positive-QTOFsplash10-004i-7900000000-b112c2a8b645bcbb11be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 10V, Positive-QTOFsplash10-00di-0190000000-b16f1dc616de8cecfe5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 10V, Positive-QTOFsplash10-00di-0190000000-79ffc92ff35f1fa970632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 30V, Positive-QTOFsplash10-00fr-2930000000-ca1a1360346ad3b18e882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 10V, Positive-QTOFsplash10-00di-0090000000-eece4fb2fe6b2df673ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flavone 30V, Positive-QTOFsplash10-00fr-2930000000-bf2d8022d73944b770e52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 10V, Positive-QTOFsplash10-00di-0090000000-38ca3854c6dc613ef0c92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 20V, Positive-QTOFsplash10-00di-0090000000-e4c89a64e226d0d9d4f52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 40V, Positive-QTOFsplash10-0uk9-9810000000-3db9238369438dc9ba102017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 10V, Negative-QTOFsplash10-00di-0090000000-fa65d36bc0c1d13e4df82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 20V, Negative-QTOFsplash10-00di-0090000000-85df3bc42e931d0eb2252017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavone 40V, Negative-QTOFsplash10-0v6v-3920000000-0890f524572f690309632017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Placenta
  • Prostate
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07776
Phenol Explorer Compound IDNot Available
FooDB IDFDB006784
KNApSAcK IDC00001040
Chemspider ID10230
KEGG Compound IDC15608
BioCyc IDCPD-8485
BiGG IDNot Available
Wikipedia LinkFlavones
METLIN ID3359
PubChem Compound10680
PDB IDNot Available
ChEBI ID42491
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1247051
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15828058 ]
  6. Barrellier MT: [Lymphedema: is there a treatment?]. Rev Med Interne. 1992 Jan-Feb;13(1):49-57. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12589031 ]
  10. Kim SJ: Effect of biflavones of Ginkgo biloba against UVB-induced cytotoxicity in vitro. J Dermatol. 2001 Apr;28(4):193-9. [PubMed:11449670 ]