Hesperetin
precursor
Showing entry for Hesperetin
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 Phytochemical | Family | Class | Sub-class | |
---|---|---|---|---|
Eriocitrin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Hesperidin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Eriodictyol | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Hesperetin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Hesperetin-7-O-glucoside | Polyphenols | Flavonoids | Flavanones | Show 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 ID | Source | Description | View |
---|---|---|---|
BML00282 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00291 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML00300 | MassBank | LC-ESI-QTOF Spectrum - 40 ev, unspecified | View Spectra |
BML00307 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00311 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML00315 | MassBank | LC-ESI-QTOF Spectrum - 40 ev, unspecified | View Spectra |
BML81380 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
BML81381 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
FIO00130 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
FIO00131 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
FIO00132 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
FIO00133 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
FIO00134 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
FIO00135 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
FIO00136 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
FIO00137 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
FIO00138 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
FIO00139 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
PR100772 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
PS078001 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS078002 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS078003 | ReSpect | N/A Spectrum - 30, [M+H]+ | View Spectra |
PS078004 | ReSpect | N/A Spectrum - 40, [M+H]+ | View Spectra |
PS078005 | ReSpect | N/A Spectrum - 50, [M+H]+ | View Spectra |
PS078007 | ReSpect | N/A Spectrum - 10, [M-H]- | View Spectra |
PS078008 | ReSpect | N/A Spectrum - 20, [M-H]- | View Spectra |
PS078009 | ReSpect | N/A Spectrum - 30, [M-H]- | View Spectra |
Food Sources
Name | Group | |||
---|---|---|---|---|
Lemon | Fruit, Citrus | Show | ||
Lime | Fruit, Citrus | Show | ||
Orange juice | Beverages, Non-alcoholic | Show | ||
Sweet orange | Fruit, Citrus | Show |
Food Sources of its Food Phytochemical(s)
Food Phytochemical | Food Source | Food Source Group | |||
---|---|---|---|---|---|
Hesperidin | Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
Eriocitrin | Lemon | Fruit, Citrus | Publications | Show | |
Hesperetin | Lemon | Fruit, Citrus | Show | ||
Eriocitrin | Lime | Fruit, Citrus | Publications | Show | |
Hesperetin | Lime | Fruit, Citrus | Show | ||
Hesperidin | Orange juice | Beverages, Non-alcoholic | Publications | Show | |
Hesperetin | Orange juice | Beverages, Non-alcoholic | Show | ||
Hesperidin | Sweet orange | Fruit, Citrus | Show | ||
Hesperetin | Sweet orange | Fruit, Citrus | 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 | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Hesperetin | Eriodictyol | in vitro (pig) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C15H12O6 | 288.063388106 | Publications | |||
Hesperetin | Hesperetin | human | plasma, urine | unchanged | 3h-5h | <20 nmol/L | 1-5% | C16H14O6 | 302.079038171 | Detailed Intervention Studies | Publications | ||
Hesperetin | 3-(3'-Hydroxyphenyl)propionic acid | in vitro (pig) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
Hesperetin | Hesperetin-3',7-diglucuronide | human | urine | host metabolism | Not Available | Not Available | Not Available | C28H30O18 | 654.143214126 | Publications | |||
Hesperetin | Hesperetin-3'-glucuronide | human rat | plasma (major), urine (major) | host metabolism | Not Available | Not Available | Not Available | C22H22O12 | 478.111126148 | Publications | |||
Hesperetin | Hesperetin-3'-sulfate | human | urine | host metabolism | Not Available | Not Available | Not Available | C16H14O9S | 382.035853205 | Publications | |||
Hesperetin | Hesperetin 5,7-diglucuronide | human | urine | host metabolism | Not Available | Not Available | Not Available | C28H30O18 | 654.143214126 | Publications | |||
Hesperetin | Hesperetin-7-glucuronide | human | plasma (major), urine (minor) | host metabolism | Not Available | Not Available | Not Available | C22H22O12 | 478.111126148 | Publications | |||
Hesperetin | Hesperetin sulfoglucuronide | human | urine, urine (major) | host metabolism | Not Available | Not Available | 1-5% | C22H22O15S | 558.4722484 | Detailed Intervention Studies | Publications | ||
Hesperetin | Homoeriodictyol | rat | plasma (minor) | Not Available | Not Available | Not Available | Not Available | C16H14O6 | 302.079038171 | Publications | |||
Hesperetin | Homoeriodictyol-4'-glucuronide | rat | plasma (major) | Not Available | Not Available | Not Available | Not Available | C22H22O12 | 478.111126148 | Publications | |||
Hesperetin | Homoeriodictyol-7-glucuronide | rat | plasma | Not Available | Not Available | Not Available | Not Available | C22H22O12 | 478.111126148 | Publications | |||
Hesperetin | Homoeriodictyol-sulfate | rat | plasma, urine | Not Available | Not Available | Not Available | Not Available | C16H14O9S | 382.3463889 | Publications | |||
Hesperetin | Phloroglucinol | in vitro (pig) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C6H6O3 | 126.031694053 | Publications | |||
Hesperetin | 4-Hydroxyhippuric acid | human | plasma, urine | host metabolism | Not Available | Not Available | Not Available | C9H9NO4 | 195.053157774 | Publications | |||
Hesperetin | Dihydroisoferulic acid | human | plasma, urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C10H12O4 | 196.073558866 | Publications | |||
Hesperetin | Dihydroisoferulic acid-3'-glucuronide | human | plasma, urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C16H18O10 | 370.08999678 | Publications | |||
Eriocitrin | Hesperetin | rat | urine | Not Available | Not Available | Not Available | Not Available | C16H14O6 | 302.079038171 | Publications | |||
Hesperidin | Hesperetin | human | plasma, urine | gut microbiota metabolite | 5h-8h | 200-500 nmol/L | 5-10% | C16H14O6 | 302.079038171 | Detailed Intervention Studies | Publications | ||
Orange flavanones | Hesperetin | human | plasma, urine | gut microbiota metabolite | 5h-8h | 50-200 nmol/L | 1-5% | C16H14O6 | 302.079038171 | Detailed Intervention Studies | Publications | ||
Eriodictyol | Hesperetin | rat | plasma, urine | Not Available | Not Available | Not Available | Not Available | C16H14O6 | 302.079038171 | Publications | |||
Hesperetin-7-O-glucoside | Hesperetin | human | plasma, urine | host metabolism | <1h | >20µmol/L | 10-30% | C16H14O6 | 302.079038171 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Orange flavanones | Hesperetin | Age | Not studied | |||
Orange flavanones | Hesperetin | Bmi | No effect | |||
Orange flavanones | Hesperetin | Ethnicity | Not studied | |||
Orange flavanones | Hesperetin | Genotype | Not studied | |||
Orange flavanones | Hesperetin | Health_status | Not studied | |||
Orange flavanones | Hesperetin | Microbiota | Not studied | |||
Orange flavanones | Hesperetin | Sex | No effect | |||
Orange flavanones | Hesperetin | Smoking | Not studied |