Structure Database (LMSD)

Common Name
Hesperetin
Systematic Name
[S,(-)]-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Synonyms
  • Eriodictyol 4'-monomethyl ether
  • 5,7,3'-Trihydroxy-4'-methoxyflavanone
LM ID
LMPK12140003
Formula
Exact Mass
Calculate m/z
302.07904
Status
Curated





Classification

Biological Context

Hesperetin is a flavonoid that has been found in citrus fruits and has diverse biological activities.1,2,3,4,5 It reduces ApoB protein levels, ACAT2 expression, and LDL degradation in HepG2 cells when used at a concentrations ranging from 10 to 200 µM.1 Hesperetin inhibits IgG-induced β-hexosaminidase release from RBL-2H3 cells (IC50 = 0.099 mg/ml).2 It inhibits LPS-induced nitric oxide (NO) production and reduces levels of inducible nitric oxide synthase (iNOS), IL-6, and IL-1β in BV-2 microglial cells.3 Hesperetin (5 mg/kg) inhibits passive cutaneous anaphylaxis in mice.2 It reduces body weight loss, colon shortening, and ulcer severity in a mouse model of TNBS-induced ulcerative colitis.4 Hesperetin reduces cortical and hippocampal neuronal apoptosis and increases time spent in the target quadrant in the Morris water maze in a mouse model of LPS-induced neuronal inflammation.5

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Citrus sinensis (#2711)
Magnoliopsida (#3398)
Synthesis and metabolic fate of hesperetin-3-14C,
J Agric Food Chem, 1976

String Representations

InChiKey (Click to copy)
AIONOLUJZLIMTK-AWEZNQCLSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1(O)C=C2O[C@H](C3=CC=C(OC)C(O)=C3)CC(=O)C2=C(O)C=1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 3
Aromatic Rings 2
Rotatable Bonds 2
Van der Waals Molecular Volume 260.74
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 2.52
Molar Refractivity 76.75

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Created at
-
Updated at
2nd Apr 2025