Identification

PhytoHub ID
PHUB000380
Name
Hesperetin
Systematic Name
5,7,3'-Trihydroxy-4'-methoxyflavanone
Synonyms
  • 4'-Methyleriodictyol
  • 5,7,3'-Trihydroxy-4'-methoxyflavanone
CAS Number
520-33-2
Average Mass
302.282
Monoisotopic Mass
302.079038171
Chemical Formula
C16H14O6
IUPAC Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI Key
AIONOLUJZLIMTK-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3
SMILES
COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
Structure

Calculated Properties

Solubility (ALOGPS)
1.38e-01 g/l
LogS (ALOGPS)
-3.34
LogP (ALOGPS)
2.52
Hydrogen Acceptors
6
Hydrogen Donors
3
Rotatable Bond Count
2
Polar Surface Area
96.22000000000001
Refractivity
77.753
Polarizability
30.27882373369036
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-4.618662915893278
pKa (strongest acidic)
7.8617017146792705
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
Flavanones

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Flavonoid metabolites
Metabolite Sub-class
Flavanones (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
EriocitrinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
HesperidinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
EriodictyolPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
HesperetinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Hesperetin-7-O-glucosidePolyphenolsFlavonoidsFlavanonesShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
O-methylated flavonoids
Direct Parent Name
4'-O-methylated flavonoids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Anisoles", "Aryl alkyl ketones", "Chromones", "Flavanones", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Organic oxides", "Oxacyclic compounds", "Phenoxy compounds", "Vinylogous acids"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4p-methoxyflavonoid-skeleton", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alkyl aryl ether", "Anisole", "Aromatic heteropolycyclic compound", "Aryl alkyl ketone", "Aryl ketone", "Benzenoid", "Benzopyran", "Chromane", "Chromone", "Ether", "Flavan", "Flavanone", "Hydrocarbon derivative", "Hydroxyflavonoid", "Ketone", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Phenol ether", "Phenoxy compound", "Vinylogous acid"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML00282MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00291MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00300MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML00307MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00311MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00315MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81380MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81381MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
FIO00130MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00131MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00132MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00133MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00134MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00135MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00136MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00137MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00138MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00139MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
PR100772MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PS078001ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS078002ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS078003ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS078004ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS078005ReSpectN/A Spectrum - 50, [M+H]+View Spectra
PS078007ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS078008ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS078009ReSpectN/A Spectrum - 30, [M-H]-View Spectra

Food Sources

NameGroup
LemonFruit, CitrusShow
LimeFruit, CitrusShow
Orange juiceBeverages, Non-alcoholicShow
Sweet orangeFruit, CitrusShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
HesperidinGrapefruit juiceBeverages, Non-alcoholic PublicationsShow
EriocitrinLemonFruit, Citrus PublicationsShow
HesperetinLemonFruit, CitrusShow
EriocitrinLimeFruit, Citrus PublicationsShow
HesperetinLimeFruit, CitrusShow
HesperidinOrange juiceBeverages, Non-alcoholic PublicationsShow
HesperetinOrange juiceBeverages, Non-alcoholicShow
HesperidinSweet orangeFruit, CitrusShow
HesperetinSweet orangeFruit, CitrusShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Hesperetin Eriodictyolin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H12O6288.063388106 Publications
Hesperetin Hesperetinhumanplasma, urineunchanged3h-5h<20 nmol/L1-5%C16H14O6302.079038171 Detailed Intervention Studies Publications
Hesperetin 3-(3'-Hydroxyphenyl)propionic acidin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Hesperetin Hesperetin-3',7-diglucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC28H30O18654.143214126 Publications
Hesperetin Hesperetin-3'-glucuronidehuman ratplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Publications
Hesperetin Hesperetin-3'-sulfatehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC16H14O9S382.035853205 Publications
Hesperetin Hesperetin 5,7-diglucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC28H30O18654.143214126 Publications
Hesperetin Hesperetin-7-glucuronidehumanplasma (major), urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Publications
Hesperetin Hesperetin sulfoglucuronidehumanurine, urine (major)host metabolismNot AvailableNot Available1-5%C22H22O15S558.4722484 Detailed Intervention Studies Publications
Hesperetin Homoeriodictyolratplasma (minor)Not AvailableNot AvailableNot AvailableNot AvailableC16H14O6302.079038171 Publications
Hesperetin Homoeriodictyol-4'-glucuronideratplasma (major)Not AvailableNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Publications
Hesperetin Homoeriodictyol-7-glucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Publications
Hesperetin Homoeriodictyol-sulfateratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC16H14O9S382.3463889 Publications
Hesperetin Phloroglucinolin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC6H6O3126.031694053 Publications
Hesperetin 4-Hydroxyhippuric acidhumanplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
Hesperetin Dihydroisoferulic acidhumanplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC10H12O4196.073558866 Publications
Hesperetin Dihydroisoferulic acid-3'-glucuronidehumanplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Eriocitrin HesperetinraturineNot AvailableNot AvailableNot AvailableNot AvailableC16H14O6302.079038171 Publications
Hesperidin Hesperetinhumanplasma, urinegut microbiota metabolite5h-8h200-500 nmol/L5-10%C16H14O6302.079038171 Detailed Intervention Studies Publications
Orange flavanones Hesperetinhumanplasma, urinegut microbiota metabolite5h-8h50-200 nmol/L1-5%C16H14O6302.079038171 Detailed Intervention Studies Publications
Eriodictyol Hesperetinratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC16H14O6302.079038171 Publications
Hesperetin-7-O-glucoside Hesperetinhumanplasma, urinehost metabolism<1h>20µmol/L10-30%C16H14O6302.079038171 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Orange flavanones HesperetinAgeNot studied
Orange flavanones HesperetinBmiNo effect
Orange flavanones HesperetinEthnicityNot studied
Orange flavanones HesperetinGenotypeNot studied
Orange flavanones HesperetinHealth_statusNot studied
Orange flavanones HesperetinMicrobiotaNot studied
Orange flavanones HesperetinSexNo effect
Orange flavanones HesperetinSmokingNot studied
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