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Showing Compound Luteolin (FDB013255)

Record Information
Version1.0
Creation date2010-04-08 22:10:36 UTC
Update date2020-09-17 15:33:11 UTC
Primary IDFDB013255
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLuteolin
DescriptionLuteolin, also known as digitoflavone or flacitran, 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). Thus, luteolin is considered to be a flavonoid lipid molecule. Luteolin is a naturally occurring flavonoid. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. Luteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number491-70-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.73ALOGPS
logP2.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.57ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.89 m³·mol⁻¹ChemAxon
Polarizability27.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O6
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
InChI KeyIQPNAANSBPBGFQ-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
Classification
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSLuteolin, 4 TMS, GC-MS Spectrumsplash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
    GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
    GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
    GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
    GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-00dj-1735900000-66504e5cc81bcf3dd0a2Spectrum
    Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad5Spectrum
    Predicted GC-MSLuteolin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546dSpectrum
    Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0490000000-b23f87f7af1af38d96862012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0690000000-74dbeef56be77f266f6e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-001i-0900000000-4b5589ca157de0b5885b2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090080000-787383a28d957fc65a9e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82d2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82d2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0790000000-814cdaf9d50189cf2f2a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0490000000-b23f87f7af1af38d96862017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0690000000-4135ff68dafc65e9f3392017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-4b5589ca157de0b5885b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-568d5c1e3df3c5693fb42017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-b20ef421e6accd0523a42017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-2ca1121832520dd96a2c2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-14b50e413340dc95fac32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-371552bb5776fd662dd92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0590000000-a412d0980f838bf496192017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0090000000-075f1c69f8e77ea5dbe92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-236ab0853a3df459fc372021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-fda1f09c1506187911ff2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-956ceb8d223bd9454f932021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-ba91f3571fdd8398c5e92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001i-0900000000-051f4eceea0c40ddb1772021-09-20View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
    ChemSpider ID4444102
    ChEMBL IDCHEMBL151
    KEGG Compound IDC01514
    Pubchem Compound ID5280445
    Pubchem Substance IDNot Available
    ChEBI ID15864
    Phenol-Explorer ID229
    DrugBank IDNot Available
    HMDB IDHMDB05800
    CRC / DFC (Dictionary of Food Compounds) IDHQG45-Z:HQG45-Z
    EAFUS IDNot Available
    Dr. Duke IDLUTEOLIN|LUETOLIN
    BIGG IDNot Available
    KNApSAcK IDC00000674
    HET IDLU2
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDLuteolin
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    Processing...
    Biological Effects and Interactions
    Health Effects / Bioactivities
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.