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Human Metabolome Database Version 3.5

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Showing metabocard for Hesperetin (HMDB05782)

Record Information
Version 3.5
Creation Date 2007-01-22 02:25:30 -0700
Update Date 2013-02-08 17:14:17 -0700
HMDB ID HMDB05782
Secondary Accession Numbers None
Metabolite Identification
Common Name Hesperetin
Description Hesperetin 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3',5,7-Trihydroxy-4'-methoxyflavanone
  2. 5,7, 3'-Trihydroxy-4'-methoxyflavanone
  3. 5,7,3'-Trihydroxy-4'-methoxyflavanone
  4. Cyanidanon 4'-Methyl Ether 1626
  5. Flavanone, 3',5, 7-trihydroxy-4'-methoxy- (VAN)
  6. Flavanone, 3',5,7-trihydroxy-4'-methoxy- (VAN) (8CI)
  7. Hesperetin
  8. Hesperin
  9. Hesperitin
  10. Prestwick_908
  11. YSO2
Chemical Formula C16H14O6
Average Molecular Weight 302.2788
Monoisotopic Molecular Weight 302.07903818
IUPAC Name (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional IUPAC Name hesperetin
CAS Registry Number 520-33-2
SMILES COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O
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 Key AIONOLUJZLIMTK-AWEZNQCLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Flavonoids
Sub Class Flavans
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Flavanones(KEGG)
  • Flavanones(Lipidmaps)
  • monomethoxyflavanone(ChEBI)
  • trihydroxyflavanone(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Benzopyran
  • Chromane
  • Ketone
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
  • Pyran
  • Resorcinol
Direct Parent Flavanones
Ontology
Status Detected and Quantified
Origin
  • Food
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 227.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 2.60 PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
Property Value Source
Water Solubility 0.14 g/L ALOGPS
LogP 2.52 ALOGPS
LogP 2.68 ChemAxon
LogS -3.34 ALOGPS
pKa (strongest acidic) 7.92 ChemAxon
pKa (strongest basic) -3.9 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 96.22 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 77.75 ChemAxon
Polarizability 29.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Blood Detected and Quantified
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0.35 (0.05-0.66) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.5 (0.033-1.0) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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100 umol/mmol creatinine Adult (>18 years old) Both Normal 24 hours after the 2-day diet started
Urine Detected and Quantified
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180 umol/mmol creatinine Adult (>18 years old) Both Normal After 2-day diet protocol
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 203 Not Available
Urine Detected and Quantified
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0.03 +/- 0.09 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.0 +/- 0.48 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID 203 Link_out
Phenol Explorer Metabolite ID 203 Link_out
FoodDB ID FDB002677
KNApSAcK ID C00000968 Link_out
Chemspider ID 65234 Link_out
KEGG Compound ID C01709 Link_out
BioCyc ID CPD-7072 Link_out
BiGG ID Not Available
Wikipedia Link Hesperetin Link_out
NuGOwiki Link HMDB05782 Link_out
Metagene Link HMDB05782 Link_out
METLIN ID Not Available
PubChem Compound 72281 Link_out
PDB ID Not Available
ChEBI ID 28230 Link_out
References
Synthesis Reference Shinoda, 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 References Not Available
Enzymes
Name: Sterol O-acyltransferase 1
Reactions:
  • acyl-CoA + cholesterol = CoA + cholesterol ester [RN:R01461]
Gene Name: SOAT1
Uniprot ID: P35610 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Microsomal triglyceride transfer protein large subunit
Reactions:
    Gene Name: MTTP
    Uniprot ID: P55157 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA