precursor

Showing entry for Luteolin

Identification

PhytoHub ID
PHUB000892
Name
Luteolin
Systematic Name
Not Available
Synonyms
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 3',4',5,7-Tetrahydroxyflavone
  • 5,7,3',4'-Tetrahydroxyflavone
  • digitoflavone
  • Luteolol
CAS Number
491-70-3
Average Mass
286.239
Monoisotopic Mass
286.047738042
Chemical Formula
C15H10O6
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
InChI Key
IQPNAANSBPBGFQ-UHFFFAOYSA-N
InChI Identifier
InChI=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
SMILES
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.38e-01 g/l
LogS (ALOGPS)
-3.32
LogP (ALOGPS)
2.73
Hydrogen Acceptors
6
Hydrogen Donors
4
Rotatable Bond Count
1
Polar Surface Area
107.22000000000001
Refractivity
74.8948
Polarizability
27.731091863737483
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.38235824096273
pKa (strongest acidic)
6.574503414493813
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavones

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavones
Direct Parent Name
Flavones
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Benzene and substituted derivatives", "Catechols", "Chromones", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organic oxides", "Organooxygen compounds", "Oxacyclic compounds", "Pyranones and derivatives", "Vinylogous acids"]
External Descriptor Annotations
["3'-hydroxyflavonoid", "Flavones and Flavonols", "flavones", "tetrahydroxyflavone"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Catechol", "Chromone", "Flavone", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Pyran", "Pyranone", "Vinylogous acid"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML00104MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00116MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00128MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML00136MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00144MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00151MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81650MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81651MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
PB000741MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB000742MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB000743MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB000744MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PR040034MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M-H]-View Spectra
PR040035MassBankLC-ESI-QTOF Spectrum - 30 eV, [M+H]+View Spectra
PR040036MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+View Spectra
PR100230MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100231MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra
PR100643MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100644MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra
PS040401ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS040402ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS040403ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS040404ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS040407ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS040408ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS040409ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS040410ReSpectN/A Spectrum - 40, [M-H]-View Spectra
PS040411ReSpectN/A Spectrum - 50, [M-H]-View Spectra
TY000143MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra
TY000144MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra

Food Sources

NameGroup
AngelicaHerbs and Spices PublicationsShow
AppleFruit, Pomes PublicationsShow
BroccoliVegetables, Cabbages PublicationsShow
Common oreganoHerbs and Spices PublicationsShow
Common sageHerbs and Spices PublicationsShow
Common thymeHerbs and Spices PublicationsShow
Globe artichokeVegetables, Other vegetables PublicationsShow
KiwiFruit, Tropical fruits PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
PeppermintHerbs and Spices PublicationsShow
RadicchioVegetables, Leaf vegetables PublicationsShow
StrawberryFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Luteolin Chrysoeriolratplasma, urinehost-gut microbiota co-metabolite<1h2-5µmol/L<1%C16H12O6300.063388106 Publications
Luteolin Luteolinratfeces, plasma, urineunchanged1h-3h5-20µmol/L<1%C15H10O6286.047738042 Publications
Luteolin Luteolin 7-O-glucuronidehuman ratplasma, urinehost metabolism<1h0.5-2µmol/L<1%C21H18O12462.07982602 Publications
Luteolin Luteolin-4-glucuronidehumanplasmahost metabolism5h-8h20-50 nmol/LNo dataC21H18O12462.07982602 Publications
Luteolin Luteolin-3-glucuronidehumanplasmahost metabolism5h-8h20-50 nmol/LNo dataC21H18O12462.07982602 Publications
Luteolin 3'-O-methyl-luteolin-7-O-Glucuronideratplasma, urinehost-gut microbiota co-metabolite<1h0.5-2µmol/L<1%C22H20O12476.095476084 Publications
Luteolin 4'-O-methyl-luteolin-3'-O-b-D-Glucuronideratplasma, urinehost-gut microbiota co-metabolite<1h0.5-2µmol/L1-5%C22H20O12476.095476084 Publications
Luteolin 4'-O-methyl-luteolin-7-O-Glucuronideratplasma, urinehost-gut microbiota co-metabolite<1h50-200 nmol/L<1%C22H20O12476.095476084 Publications
Luteolin Luteolin-3'-O-Sulfatehumanplasmahost metabolism3h-5h0.5-2µmol/LNo dataC15H10O9S366.004553076 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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