CAS 59870-68-7|4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.02,7]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol|4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.02</su...

General Information

Structure

Molecular Formula

C₂₀H₂₀O₄

Molecular Mass

324.3704

Exact Mass

324.13615912

Charge

InChI

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

InChIKey

LBQIJVLKGVZRIW-ZDUSSCGKSA-N

Canonic Smiles

Oc1ccc(c(c1)O)[C@@H]1COc2c(C1)ccc1c2C=CC(O1)(C)C

Isomeric Smiles

O1c2c3C=CC(Oc3ccc2C[C@H](c2ccc(O)cc2O)C1)(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

4.09

LogD (pH = 5.5)

4.09

Log P

4.09

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.62

Polar Surface Area

58.92

Polarizability

34.65

Molar Refractivity

93.35

LOG S

-4.33

Data Source

Names and Identifiers

IUPAC name

4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol 4-[(3R)-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol

IUPAC Traditional name

4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol glabridin

Synonyms

GlabridinGlabridinGlabridin(R)-4-(3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl)-1,3-benzenediol4-[(3R)-3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl]-1,3-benzenediol4-[3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]-1,3-benzenediolglabridin

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

CHEMBL

Chemspider ID

Wikipedia Title

Beilstein Number

MDL Number

PubChem SID

KNApSAcK Database

PubMed Citation Links

LIPID MAPS Instance

ACToR Database

CHEBI ID

HMDB Database

KEGG ID

CompTox Database

Protein Data Bank

SureChEMBL Database

Reaxys Registry

MetaboLights Database

MTBLS2871

Registration numbers

Properties

Physical Property

Safety Information

Pharmacology Properties

Mechanism of Action

Melanogenesis inhibitor

Tyrosinase inhibitor

Human cytochrome P450S 3A4, 2B6, 2C9 inhibitor

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

G9548

Biochem/physiol Actions
Glabridin is a bio-available isoflavan isolated from licorice (Glycyrrhiza glabra L.) root extract. Glabridin has been reported to posses varies biological activities including strong antioxidant activity, antioxidant against LDL oxidation, anti-Helicobacter pylori properties, estrogen-like activity and antinephritic and radical scavenging activities. Also it appears to inhibit serotonin re-uptake, melanogenesis, inflammation and cytochrome P450 3A4, 2B6, and 2C9.

A member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4' and a 2,2-dimethyl-2H-pyran group across positions 7 and 8 respectively.

Molecule Details

References

PubChem Literature

From Data Sources

• 7. Choi, E. The licorice root derived isoflavan glabridin increases the function of osteoblastic

• Anticancer Res 20 (2000), pp. 2525?536.

• 4. T. Yokota, H. Nishio, Y. Kubota and M. Mizoguchi, The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation, Pigment Cell Res 11 (1998), pp. 355?61.

• 6. U.M. Kent, M. Aviram, M. Rosenblat and P.F. Hollenberg, The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9,

• 1. T. Fukai, H. Sakagami, M. Toguchi, F. Takayama, I. Iwakura and T. Atsumi, Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines,

• 3. S. Tamir, M. Eizenberg, D. Somjen, S. Izrael and J. Vaya, Estrogen-like activity of glabrene and other constituents isolated from licorice root, J Steroid Biochem Mol Biol 78 (2001), pp. 291?98.

• Drug Metab Dispos 30 (2002), pp. 709?15.

• 2. T. Fukai, A. Marumo, K. Kaitou, T. Kanda, S. Terada and T. Nomura, Anti-Helicobacter pylori flavonoids from licorice extract, Life Sci 71 (2002), pp. 1449?463

• 5. O. Nerya, J. Vaya, R. Musa, S. Izrael, R. Ben-Arie and S. Tamir, Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots, J Agric Food Chem 51 (2003), pp. 1201?207.

• MC3T3-E1 cells. Biochem. Pharm. 2005, 70, 363-368.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol 4-[(3R)-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol

IUPAC Traditional name

4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol glabridin

Synonyms

Registration numbers

CAS Number

PubChem CID

CHEMBL

Chemspider ID

Wikipedia Title

Beilstein Number

MDL Number

PubChem SID

KNApSAcK Database

PubMed Citation Links

LIPID MAPS Instance

ACToR Database

CHEBI ID

HMDB Database

KEGG ID

CompTox Database

Protein Data Bank

SureChEMBL Database

Reaxys Registry

MetaboLights Database

Molecule Details

G9548

A member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4' and a 2,2-dimethyl-2H-pyran group across positions 7 and 8 respectively.

References

PubChem Literature

From Data Sources

• 7. Choi, E. The licorice root derived isoflavan glabridin increases the function of osteoblastic

• Anticancer Res 20 (2000), pp. 2525?536.

• 4. T. Yokota, H. Nishio, Y. Kubota and M. Mizoguchi, The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation, Pigment Cell Res 11 (1998), pp. 355?61.

• 6. U.M. Kent, M. Aviram, M. Rosenblat and P.F. Hollenberg, The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9,

• 1. T. Fukai, H. Sakagami, M. Toguchi, F. Takayama, I. Iwakura and T. Atsumi, Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines,

• Drug Metab Dispos 30 (2002), pp. 709?15.

• 2. T. Fukai, A. Marumo, K. Kaitou, T. Kanda, S. Terada and T. Nomura, Anti-Helicobacter pylori flavonoids from licorice extract, Life Sci 71 (2002), pp. 1449?463

• 5. O. Nerya, J. Vaya, R. Musa, S. Izrael, R. Ben-Arie and S. Tamir, Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots, J Agric Food Chem 51 (2003), pp. 1201?207.

• MC3T3-E1 cells. Biochem. Pharm. 2005, 70, 363-368.

Bioactivity

PubChem BioAssay

Properties

Physical Property

Safety Information

Pharmacology Properties

Mechanism of Action

Melanogenesis inhibitor

Tyrosinase inhibitor

Human cytochrome P450S 3A4, 2B6, 2C9 inhibitor

Molecule

ID:127561