Record Information
Version1.0
Creation date2010-04-08 22:10:36 UTC
Update date2018-05-29 01:04:05 UTC
Primary IDFDB013255
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLuteolin
DescriptionFlavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Anne's Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard.
CAS Number491-70-3
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyroneChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
3',4',5,7-TetrahydroxyflavoneChEBI
5,7,3',4'-TetrahydroxyflavoneChEBI
DigitoflavoneChEBI
FlacitranChEBI
LuteololChEBI
SalifazideChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-oneHMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-oneHMDB
LuteolineHMDB
3',4',5,7-Tetrahydroxy-flavoneHMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CIdb_source
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-onebiospider
3',4',5,7-Tetrahydroxy-Flavonebiospider
4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-biospider
Cyanidenon 1470biospider
Daphneflavonoldb_source
Flavone, 3',4',5,7-tetrahydroxy-biospider
Flavopurpoldb_source
Luteolindb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.94%; H 3.52%; O 33.54%DFC
Melting PointMp 328-330° (325°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.53PERRISSOUD,D & TESTA,B (1986)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data351 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1735900000-66504e5cc81bcf3dd0a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-000i-0090000000-c8d8c5048f03b4f9ad5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0490000000-b23f87f7af1af38d9686View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0f79-1940000000-006d75dee56e7481a44fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0290000000-e0e08b588cde4ec7d7c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0190000000-f142e0417f0f94a4623bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0f79-1920000000-42c47240052ab59116f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0690000000-74dbeef56be77f266f6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-001i-0900000000-4b5589ca157de0b5885bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-000i-0090000000-7b507d1551bc27fa6952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090080000-787383a28d957fc65a9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0790000000-814cdaf9d50189cf2f2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udr-0930000000-ad4b17e3762693841171View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0490000000-b23f87f7af1af38d9686View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0690000000-4135ff68dafc65e9f339View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-4b5589ca157de0b5885bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-1682faadbefced000a71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-fd32d917fb0b393a99aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-5690000000-407bf2d6b008427648faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c5cbc6ffe79c8cd57604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-147d7dcca6436066ce44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxu-4960000000-ee3c93ba84300846c333View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti atherogenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti complementaryDUKE
anti dermatic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti feedantDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lymphomicDUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
anti proliferantDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
aphidifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
apoptoticDUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
beta-glucuronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
differentiatorDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
estrogenicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hyaluronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hypocholesterolemicDUKE
ICAM-1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
IKK inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
iNOS inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
iodothyronine-deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
mitogen-activated-protein-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
metalloproteinase inhibitor50664 DUKE
matrix-metalloproteinase-9 inhibitor50664 DUKE
myorelaxantDUKE
neutral-endopeptidase inhibitor59107 Any EC 3.4.* (hydrolases acting on peptide bond) inhibitor that interferes with the activity of a metalloendopeptidase (EC 3.4.24.*).DUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
proliferantDUKE
prostaglandin-synthetase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
succinoxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
TNF-alpha inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
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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.
— 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.