Naringenin
precursor
Showing entry for Naringenin
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
External Links
- ChEBI
- 50202
- PubChem
- 932
- Chemistry Dashboard
- DTXSID50274239
- MetaboLights
- MTBLC50202
- FooDB (Compounds)
- FDB016687
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 Phytochemical | Family | Class | Sub-class | |
---|---|---|---|---|
Naringenin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Naringin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Narirutin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Spectra from Online Resources
Record ID | Source | Description | View |
---|---|---|---|
BML00645 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00656 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML00667 | MassBank | LC-ESI-QTOF Spectrum - 40 ev, unspecified | View Spectra |
BML00676 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00684 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML00692 | MassBank | LC-ESI-QTOF Spectrum - 40 ev, unspecified | View Spectra |
BML81780 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
BML81781 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
FIO00205 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
FIO00206 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
FIO00207 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
FIO00208 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
FIO00209 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
FIO00210 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
FIO00211 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
FIO00212 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
FIO00213 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
FIO00214 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
JP010999 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
ML005001 | MassBank | LC-ESI-ITFT Spectrum - 50 % (nominal), unspecified | View Spectra |
OUF00380 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
OUF00381 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PB000122 | MassBank | LC-ESI-QTOF Spectrum - 15 eV, unspecified | View Spectra |
PB000123 | MassBank | LC-ESI-QTOF Spectrum - 25 eV, unspecified | View Spectra |
PB000124 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
PB000125 | MassBank | LC-ESI-QTOF Spectrum - 55 eV, unspecified | View Spectra |
PB002401 | MassBank | LC-ESI-QTOF Spectrum - 15 eV, unspecified | View Spectra |
PB002402 | MassBank | LC-ESI-QTOF Spectrum - 25 eV, unspecified | View Spectra |
PB002403 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
PB002404 | MassBank | LC-ESI-QTOF Spectrum - 55 eV, unspecified | View Spectra |
PR040041 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M-H]- | View Spectra |
PR040042 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, [M-H]- | View Spectra |
PR040043 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, [M+H]+ | View Spectra |
PR040044 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+ | View Spectra |
PS040701 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS040702 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS040703 | ReSpect | N/A Spectrum - 30, [M+H]+ | View Spectra |
PS040704 | ReSpect | N/A Spectrum - 40, [M+H]+ | View Spectra |
PS040705 | ReSpect | N/A Spectrum - 50, [M+H]+ | View Spectra |
PS040707 | ReSpect | N/A Spectrum - 10, [M-H]- | View Spectra |
PS040708 | ReSpect | N/A Spectrum - 20, [M-H]- | View Spectra |
PS040709 | ReSpect | N/A Spectrum - 30, [M-H]- | View Spectra |
PS040710 | ReSpect | N/A Spectrum - 40, [M-H]- | View Spectra |
PS040711 | ReSpect | N/A Spectrum - 50, [M-H]- | View Spectra |
PS085701 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS085702 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS085703 | ReSpect | N/A Spectrum - 30, [M+H]+ | View Spectra |
PS085704 | ReSpect | N/A Spectrum - 40, [M+H]+ | View Spectra |
PS085705 | ReSpect | N/A Spectrum - 50, [M+H]+ | View Spectra |
PS085707 | ReSpect | N/A Spectrum - 10, [M-H]- | View Spectra |
PS085708 | ReSpect | N/A Spectrum - 20, [M-H]- | View Spectra |
PS085709 | ReSpect | N/A Spectrum - 30, [M-H]- | View Spectra |
PS085710 | ReSpect | N/A Spectrum - 40, [M-H]- | View Spectra |
PS085711 | ReSpect | N/A Spectrum - 50, [M-H]- | View Spectra |
Food Sources
Name | Group | |||
---|---|---|---|---|
Cherry tomato | Vegetables, Fruit vegetables | Publications | Show | |
Grapefruit | Fruit, Citrus | Publications | Show | |
Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
Sweet orange | Fruit, Citrus | Publications | Show | |
Tomato | Vegetables, Fruit vegetables | Publications | Show |
Food Sources of its Food Phytochemical(s)
Food Phytochemical | Food Source | Food Source Group | |||
---|---|---|---|---|---|
Naringenin | Cherry tomato | Vegetables, Fruit vegetables | Publications | Show | |
Narirutin | Globe artichoke | Vegetables, Other vegetables | Publications | Show | |
Naringenin | Grapefruit | Fruit, Citrus | Publications | Show | |
Naringin | Grapefruit | Fruit, Citrus | Publications | Show | |
Narirutin | Grapefruit | Fruit, Citrus | Publications | Show | |
Naringenin | Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
Naringin | Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
Narirutin | Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
Naringin | Lemon | Fruit, Citrus | Publications | Show | |
Naringin | Lime | Fruit, Citrus | Publications | Show | |
Narirutin | Orange juice | Beverages, Non-alcoholic | Publications | Show | |
Naringin | Sour orange | Fruit, Citrus | Publications | Show | |
Naringenin | Sweet orange | Fruit, Citrus | Publications | Show | |
Naringin | Sweet orange | Fruit, Citrus | Publications | Show | |
Narirutin | Sweet orange | Fruit, Citrus | Publications | Show | |
Naringenin | Tomato | Vegetables, Fruit vegetables | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Naringenin | Naringenin | human | plasma, urine | unchanged | 1h-3h | <20 nmol/L | 5-10% | C15H12O5 | 272.068473486 | Detailed Intervention Studies | Publications | ||
Naringenin | Coumaric acid (p-) | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H8O3 | 164.047344118 | Publications | |||
Naringenin | Phloretic acid | in vitro (pig) rat | urine (major) | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
Naringenin | 3-Phenylpropionic acid | in vitro (pig) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O2 | 150.068079562 | Publications | |||
Naringenin | Naringenin-4'-glucuronide | human | plasma (major), urine (major) | host metabolism | Not Available | Not Available | Not Available | C21H20O11 | 448.100561464 | Publications | |||
Naringenin | Naringenin-7-glucuronide | human | plasma (major), urine (major) | host metabolism | Not Available | Not Available | Not Available | C21H20O11 | 448.100561464 | Publications | |||
Naringenin | Naringenin-diglucuronide | human | urine (minor) | host metabolism | Not Available | Not Available | Not Available | C27H28O17 | 624.5095093 | Publications | |||
Naringenin | Naringenin-sulfate | human | plasma (major), urine (major) | host metabolism | Not Available | Not Available | Not Available | C15H12O8S | 352.320095 | Publications | |||
Naringenin | Naringenin-sulfoglucuronide | human | plasma (minor) | Not Available | Not Available | Not Available | Not Available | C21H20O14S | 528.4459545 | Publications | |||
Naringenin | Phloroglucinol | in vitro (human) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C6H6O3 | 126.031694053 | Publications | |||
Naringenin | Naringenin-glucuronide | human | plasma, urine | host metabolism | 1h-3h | 50-200 nmol/L | > 90% | C21H20O11 | 448.100561482 | Detailed Intervention Studies | Publications | ||
Naringin | Naringenin | human | plasma, urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C15H12O5 | 272.068473486 | Detailed Intervention Studies | Publications | ||
Narirutin | Naringenin | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C15H12O5 | 272.068473486 | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Orange flavanones | Naringenin | Age | Not studied | |||
Orange flavanones | Naringenin | Bmi | No effect | |||
Orange flavanones | Naringenin | Ethnicity | Not studied | |||
Orange flavanones | Naringenin | Genotype | Not studied | |||
Orange flavanones | Naringenin | Health_status | Not studied | |||
Orange flavanones | Naringenin | Microbiota | Not studied | |||
Orange flavanones | Naringenin | Sex | No effect | |||
Orange flavanones | Naringenin | Smoking | Not studied |