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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-22 09:25:30 UTC
Update Date2017-10-23 19:04:18 UTC
HMDB IDHMDB0005782
Secondary Accession Numbers
  • HMDB05782
Metabolite Identification
Common NameHesperetin
DescriptionHesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. Hesperetin is a biomarker for the consumption of citrus fruits.
Structure
Thumb
Synonyms
ValueSource
(-)-(S)-HesperetinChEBI
(-)-HesperetinChEBI
(S)-2,3-dihydro-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
3',5,7-Trihydroxy-4'-methoxyflavanoneChEBI
5,7, 3'-Trihydroxy-4'-methoxyflavanoneHMDB
5,7,3'-Trihydroxy-4'-methoxyflavanoneHMDB
Cyanidanon 4'-methyl ether 1626HMDB
HesperinHMDB
HesperitinHMDB
Prestwick_908HMDB
YSO2HMDB
Chemical FormulaC16H14O6
Average Molecular Weight302.2788
Monoisotopic Molecular Weight302.07903818
IUPAC Name(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namehesperetin
CAS Registry Number520-33-2
SMILES
COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1
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/t14-/m0/s1
InChI KeyAIONOLUJZLIMTK-AWEZNQCLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • Flavanone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Aryl alkyl ketone
  • Anisole
  • Phenol ether
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point227.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.60PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.52ALOGPS
logP2.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability29.3 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0792000000-043d1ca82d4702349341View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-3860980000-a1715e067e13bbdada3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-da94c45c0a6bde515ea3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0169000000-5d9b7fba914d229018a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-053i-0920000000-b6ab2fed21176a341b28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-b833c4c244a2461530ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-32f8b49c4bc1df10782aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0iki-0930000000-20176d350f94ae4a84edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-2910000000-54a5cf5acd3ca156389eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-2a5462077f9208908972View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0139000000-0c743a741d25379011aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w2i-0961000000-8406f0210238c955e23eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gw0-0920000000-b833f9a80eb4ea8d3b13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0910000000-943c442894f2e6d36fe3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0925000000-20d9733844b315a5aac1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f7c-0092000000-df166f951c1d37996e32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f79-0092000000-28f5918da43818b380bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-fda4f743655d07e229ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0906000000-4ff368578ae1225967b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0900000000-aaca372b112b1730d913View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-8857224e3cadbbf71a7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0329000000-4364410cdc5a65b92032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0944000000-edd7b755d11b9331e6c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-3910000000-9e449d46da8305c0b794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-21473197ac3beced4628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0569000000-1e4d2574c341d9d9124fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbl-4940000000-c9a717aa36bf4402e6c7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0222 +/- 0.0449 uMAdult (>18 years old)Female
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodDetected and Quantified0.35 (0.05-0.66) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.5 (0.033-1.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.0011 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0011 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00154 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0216 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.039 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.180 +/- 0.510 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.200 +/- 1.0133 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified100 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified180 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineDetected and Quantified0.03 +/- 0.09 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.0 +/- 0.48 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0667 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.246 +/- 0.359 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID203
Phenol Explorer Metabolite ID203
FoodDB IDFDB002677
KNApSAcK IDC00000968
Chemspider ID65234
KEGG Compound IDC01709
BioCyc IDCPD-7072
BiGG IDNot Available
Wikipedia LinkHesperetin
METLIN IDNot Available
PubChem Compound72281
PDB IDNot Available
ChEBI ID28230
References
Synthesis ReferenceShinoda, J.; Kawagoye, M. Polyhydroxychalcones, polyhydroxyhydrochalcones and polyhydroxyflavanones. III. Synthesis of hesperetin. Yakugaku Zasshi (1928), 48 938-41.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in acyl-CoA binding
Specific function:
Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular weight:
58130.665
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915

Transporters

General function:
Involved in lipid transporter activity
Specific function:
Catalyzes the transport of triglyceride, cholesteryl ester, and phospholipid between phospholipid surfaces. Required for the secretion of plasma lipoproteins that contain apolipoprotein B
Gene Name:
MTTP
Uniprot ID:
P55157
Molecular weight:
99350.3