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
asahina
InChI Key
FTVWIRXFELQLPI-UHFFFAOYNA-N
InChI Identifier
InChI=1/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 Precursor

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanones

Spectra

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

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Naringenin 3-Phenylpropionic acidin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableC9H10O2150.068079562 Publications
Naringenin Naringenin-4'-glucuronidehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableC21H20O11448.100561464 Publications
Naringenin Naringenin-7-glucuronidehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableC21H20O11448.100561464 Publications
Naringenin Naringenin-diglucuronidehumanurine (minor)host metabolismNot AvailableNot AvailableC27H28O17624.5095093 Publications
Naringenin Naringenin-sulfatehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableC15H12O8S352.320095 Publications
Naringenin Naringenin-sulfoglucuronidehumanplasma (minor)Not AvailableNot AvailableNot AvailableC21H20O14S528.4459545 Publications
Naringenin Coumaric acid (p-)raturineNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Naringenin Phloroglucinolin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableC6H6O3126.031694053 Publications
Naringenin Phloretic acidin vitro (pig) raturine (major)host-gut microbiota co-metaboliteNot AvailableNot AvailableC9H10O3166.062994182 Publications
Naringenin Naringeninhumanplasma, urineunchanged1h-3h<20 nmol/L5-10%C15H12O5272.068473486 Detailed Intervention Studies Publications
Naringenin Naringenin-glucuronidehumanplasma, urinehost metabolism1h-3h50-200 nmol/L> 90%C21H20O11448.100561482 Detailed Intervention Studies Publications
Orange flavanones Naringeninhumanplasma, urinegut microbiota metabolite3h-5h50-200 nmol/L10-30%C15H12O5272.068473486 Detailed Intervention Studies Publications
Naringin Naringeninhumanplasma, urinegut microbiota metaboliteNot AvailableNot AvailableC15H12O5272.068473486 Detailed Intervention Studies
Narirutin NaringeninNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H12O5272.068473486 Detailed Intervention Studies

Inter-Individual Variations Metabolism

PrecursorMetaboliteEffectValue
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