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Structure Database (LMSD)

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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

C₁₆H₁₄O₆

Exact Mass

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302.07904

Status

Curated

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Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavanones [PK1214]

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

1. Wilcox, L.J., Borradaile, N.M., de Dreu, L.E., et al. Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP. J. Lipid Res. 42(5), 725-734 (2001).

2. Lee, N.K., Choi, S.H., Park, S.H., et al. Antiallergic activity of hesperidin is activated by intestinal microflora. Pharmacology 71(4), 174-180 (2004).

3. Jo, S.H., Kim, M.E., Cho, J.H., et al. Hesperetin inhibits neuroinflammation on microglia by suppressing inflammatory cytokines and MAPK pathways. Arch. Pharm. Res. 42(8), 695-703 (2019).

4. He, W., Liu, M., Li, Y., et al. Flavonoids from Citrus aurantium ameliorate TNBS-induced ulcerative colitis through protecting colonic mucus layer integrity. Eur. J. Pharmacol. 857, 172456 (2019).

5. Muhammad, T., Ikram, M., Ullah, R., et al. Hesperetin, a citrus flavonoid, attenuates LPS-induced neuroinflammation, apoptosis and memory impairments by modulating TLR4/NF-κB signaling. Nutrients 11(3), 648 (2019).

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

DOI: 10.1021/jf60207a031 Published May 1, 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

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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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Updated at

2nd Apr 2025