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Structure Database (LMSD)

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Common Name

Glabridin

Systematic Name

4-[[(R)-3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran]-3β-yl]-1,3-benzenediol

Synonyms

LM ID

LMPK12080012

Formula

C₂₀H₂₀O₄

Exact Mass

Calculate m/z

324.13616

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View NP-MRD ID(NMR) spectrum

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Isoflavans [PK1208]

Biological Context

Glabridin is a prenylated isoflavonoid found in licorice root extract that is reported to possess antiviral, antimicrobial, anti-inflammatory, antidiabetic, antiatherogenic, antioxidant, antitumor, and estrogen-like properties.^1,2,3 These diverse biological activities are largely related to the capacity of glabridin to down-regulate reactive oxygen species, bind to antioxidant effectors, and act as a selective estrogen receptor modulator.⁴

This information has been provided by Cayman Chemical

References

1. Lee, K.J., Oh, Y.C., Cho, W.K., et al. Antioxidant and anti-inflammatory activity determination of one hundred kinds of pure chemical compounds using offline and online screening HPLC assay. Evid. Based Complement. Alternat. Med. 165457 (2015).

2. Ming, L.J., and Yin, A.C. Therapeutic effects of glycyrrhizic acid. Nat. Prod. Commun. 8(3), 415-418 (2013).

3. Wang, L., Yang, R., Yuan, B., et al. The antiviral and antimicrobial activities of licorice, a widely-used Chinese herb. Acta Pharm. Sin. B 5(4), 310-315 (2015).

4. Simmler, C., Pauli, G.F., and Chen, S.-N. Phytochemistry and biological properties of glabridin. Fitoterapia 90, 160-184 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Glycyrrhiza glabra (#49827)

Magnoliopsida (#3398)

Antimicrobial agents from higher plants. Antimicrobial isoflavanoids and related substances from Glycyrrhiza glabra L. var. typica.,
J Nat Prod, 1980

Pubmed ID: 7381508

DOI: 10.1021/np50008a004

String Representations

InChiKey (Click to copy)

LBQIJVLKGVZRIW-ZDUSSCGKSA-N

InChi (Click to copy)

InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1

SMILES (Click to copy)

C12OC(C)(C)C=CC1=C1OC[C@@]([H])(C3C(O)=CC(O)=CC=3)CC1=CC=2

Other Databases

KEGG ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

PDB ID

Calculated Physicochemical Properties

Heavy Atoms 24

Rings 4

Aromatic Rings 2

Rotatable Bonds 1

Van der Waals Molecular Volume 300.00

Topological Polar Surface Area 63.06

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 4

logP 4.57

Molar Refractivity 92.90

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Updated at

21st Nov 2025