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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 09:25:30 UTC
Update Date2021-09-14 14:57:29 UTC
HMDB IDHMDB0005782
Secondary Accession Numbers
  • HMDB05782
Metabolite Identification
Common NameHesperetin
DescriptionHesperetin, also known as prestwick_908 or YSO2, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, hesperetin is considered to be a flavonoid lipid molecule. Hesperetin also seems to upregulate the LDL receptor. Hesperetin, in the form of its glycoside , is the predominant flavonoid in lemons and oranges. Hesperetin is a drug which is used for lowering cholesterol and, possibly, otherwise favorably affecting lipids. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity. Hesperetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hesperetin is a bitter tasting compound. Hesperetin is found, on average, in the highest concentration within a few different foods, such as limes, persian limes, and sweet oranges and in a lower concentration in pummelo, welsh onions, and lemons. Hesperetin has also been detected, but not quantified, in several different foods, such as yellow bell peppers, carrots, rapinis, hazelnuts, and beers. Hesperetin is a biomarker for the consumption of citrus fruits. Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT1 and ACAT2) and it reduces microsomal triglyceride transfer protein (MTP) activity.
Structure
Data?1582752364
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
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point227.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.60PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker178.48830932474
[M+H]+Baker176.54430932474
[M-H]-Not Available178.488http://allccs.zhulab.cn/database/detail?ID=AllCCS00001935
[M+H]+Not Available176.544http://allccs.zhulab.cn/database/detail?ID=AllCCS00001935
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP10(2.52) g/LALOGPS
logP10(2.68) g/LChemAxon
logS10(-3.3) g/LALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.18231661259
DarkChem[M-H]-174.38931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HesperetinCOC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O14225.7Standard polar33892256
HesperetinCOC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O12998.8Standard non polar33892256
HesperetinCOC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O12989.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hesperetin,1TMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C2928.7Semi standard non polar33892256
Hesperetin,1TMS,isomer #2COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O2949.6Semi standard non polar33892256
Hesperetin,1TMS,isomer #3COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O2966.5Semi standard non polar33892256
Hesperetin,2TMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C2867.3Semi standard non polar33892256
Hesperetin,2TMS,isomer #2COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C2884.8Semi standard non polar33892256
Hesperetin,2TMS,isomer #3COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O2867.4Semi standard non polar33892256
Hesperetin,3TMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C2856.0Semi standard non polar33892256
Hesperetin,1TBDMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3214.6Semi standard non polar33892256
Hesperetin,1TBDMS,isomer #2COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O3227.3Semi standard non polar33892256
Hesperetin,1TBDMS,isomer #3COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O3241.2Semi standard non polar33892256
Hesperetin,2TBDMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C3380.3Semi standard non polar33892256
Hesperetin,2TBDMS,isomer #2COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3394.8Semi standard non polar33892256
Hesperetin,2TBDMS,isomer #3COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O3392.6Semi standard non polar33892256
Hesperetin,3TBDMS,isomer #1COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C3537.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hesperetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0792000000-043d1ca82d47023493412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hesperetin GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-3860980000-a1715e067e13bbdada3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hesperetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF 10V, Negative-QTOFsplash10-0udi-0009000000-da94c45c0a6bde515ea32017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF 20V, Negative-QTOFsplash10-0udi-0169000000-5d9b7fba914d229018a62017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF 40V, Negative-QTOFsplash10-053i-0920000000-b6ab2fed21176a341b282017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF , Negative-QTOFsplash10-0udi-0009000000-b833c4c244a2461530ec2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF 10V, Negative-QTOFsplash10-0udi-0009000000-32f8b49c4bc1df10782a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin ESI-TOF 30V, Negative-QTOFsplash10-0iki-0930000000-20176d350f94ae4a84ed2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-0udi-0009000000-2a5462077f92089089722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-0udi-0139000000-0c743a741d25379011aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-0w2i-0961000000-8406f0210238c955e23e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-0gw0-0920000000-b833f9a80eb4ea8d3b132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-052r-0910000000-943c442894f2e6d36fe32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOFsplash10-0zfr-0925000000-20d9733844b315a5aac12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin Linear Ion Trap , negative-QTOFsplash10-0f7c-0092000000-df166f951c1d37996e322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin Linear Ion Trap , negative-QTOFsplash10-0f79-0092000000-28f5918da43818b380bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 10V, Negative-QTOFsplash10-0udi-0009000000-2a5462077f92089089722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 40V, Negative-QTOFsplash10-0gw0-0920000000-b833f9a80eb4ea8d3b132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 50V, Negative-QTOFsplash10-052r-0910000000-943c442894f2e6d36fe32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 20V, Negative-QTOFsplash10-0udi-0983000000-bce6d9dd08ed8a9f1bfe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 10V, Negative-QTOFsplash10-0udi-0009000000-ee75ac55375bccdbc5462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 30V, Negative-QTOFsplash10-0w2i-0961000000-8406f0210238c955e23e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 40V, Negative-QTOFsplash10-0a4r-0910000000-95b197d21308c2a4fcd42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 20V, Negative-QTOFsplash10-0udi-0139000000-0c743a741d25379011aa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 10V, Negative-QTOFsplash10-0udi-0009000000-89e5174c941f8e8179b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 40V, Negative-QTOFsplash10-0a4r-0910000000-7499953ac947716fca532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hesperetin 20V, Negative-QTOFsplash10-0udi-0693000000-063003ec193c4492dab22021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0222 +/- 0.0449 uMAdult (>18 years old)Female
Normal
details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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 but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 203 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01094
Phenol Explorer Compound ID203
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000471
Good Scents IDNot Available
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