Identification

PhytoHub ID
PHUB000387
Name
Naringenin
Systematic Name
4',5,7-trihydroxyflavan-4-one
Synonyms
  • 5,7,4'-Trihydroxyflavanone
CAS Number
Not Available
Average Mass
272.256
Monoisotopic Mass
272.068473486
Chemical Formula
C15H12O5
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI Key
FTVWIRXFELQLPI-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
SMILES
OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
Structure

Calculated Properties

Solubility (ALOGPS)
2.14e-01 g/l
LogS (ALOGPS)
-3.11
LogP (ALOGPS)
2.47
Hydrogen Acceptors
5
Hydrogen Donors
3
Rotatable Bond Count
1
Polar Surface Area
86.99
Refractivity
71.28980000000001
Polarizability
27.314576908172157
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-4.950228081125502
pKa (strongest acidic)
7.856156114596552
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
NaringeninPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
NaringinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
NarirutinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical

Spectra from Online Resources

Record IDSourceDescriptionView
BML00645MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00656MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00667MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML00676MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00684MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00692MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81780MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81781MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
FIO00205MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00206MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00207MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00208MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00209MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00210MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00211MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00212MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00213MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00214MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
JP010999MassBankEI-B Spectrum - -, [M]+*View Spectra
ML005001MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra
OUF00380MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
OUF00381MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB000122MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB000123MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB000124MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB000125MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB002401MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB002402MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB002403MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB002404MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PR040041MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M-H]-View Spectra
PR040042MassBankLC-ESI-QTOF Spectrum - 30 eV, [M-H]-View Spectra
PR040043MassBankLC-ESI-QTOF Spectrum - 30 eV, [M+H]+View Spectra
PR040044MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+View Spectra
PS040701ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS040702ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS040703ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS040704ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS040705ReSpectN/A Spectrum - 50, [M+H]+View Spectra
PS040707ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS040708ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS040709ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS040710ReSpectN/A Spectrum - 40, [M-H]-View Spectra
PS040711ReSpectN/A Spectrum - 50, [M-H]-View Spectra
PS085701ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS085702ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS085703ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS085704ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS085705ReSpectN/A Spectrum - 50, [M+H]+View Spectra
PS085707ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS085708ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS085709ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS085710ReSpectN/A Spectrum - 40, [M-H]-View Spectra
PS085711ReSpectN/A Spectrum - 50, [M-H]-View Spectra

Food Sources

NameGroup
Cherry tomatoVegetables, Fruit vegetables PublicationsShow
GrapefruitFruit, Citrus PublicationsShow
Grapefruit juiceBeverages, Non-alcoholic PublicationsShow
Sweet orangeFruit, Citrus PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow

Food Sources of its Food Phytochemical(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Naringenin Naringeninhumanplasma, urineunchanged1h-3h<20 nmol/L5-10%C15H12O5272.068473486 Detailed Intervention Studies Publications
Naringenin Coumaric acid (p-)raturineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Naringenin Phloretic acidin vitro (pig) raturine (major)host-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Naringenin 3-Phenylpropionic acidin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O2150.068079562 Publications
Naringenin Naringenin-4'-glucuronidehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC21H20O11448.100561464 Publications
Naringenin Naringenin-7-glucuronidehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC21H20O11448.100561464 Publications
Naringenin Naringenin-diglucuronidehumanurine (minor)host metabolismNot AvailableNot AvailableNot AvailableC27H28O17624.5095093 Publications
Naringenin Naringenin-sulfatehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC15H12O8S352.320095 Publications
Naringenin Naringenin-sulfoglucuronidehumanplasma (minor)Not AvailableNot AvailableNot AvailableNot AvailableC21H20O14S528.4459545 Publications
Naringenin Phloroglucinolin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC6H6O3126.031694053 Publications
Naringenin Naringenin-glucuronidehumanplasma, urinehost metabolism1h-3h50-200 nmol/L> 90%C21H20O11448.100561482 Detailed Intervention Studies Publications
Naringin Naringeninhumanplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H12O5272.068473486 Detailed Intervention Studies Publications
Narirutin NaringeninNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H12O5272.068473486 Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Orange flavanones NaringeninAgeNot studied
Orange flavanones NaringeninBmiNo effect
Orange flavanones NaringeninEthnicityNot studied
Orange flavanones NaringeninGenotypeNot studied
Orange flavanones NaringeninHealth_statusNot studied
Orange flavanones NaringeninMicrobiotaNot studied
Orange flavanones NaringeninSexNo effect
Orange flavanones NaringeninSmokingNot studied
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