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...

基本信息

化学结构

分子式

C₂₀H₂₀O₄

分子量

324.3704

精确质量

324.13615912

电荷

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

计算属性

JChem

LogD (pH = 7.4)

4.09

LogD (pH = 5.5)

4.09

Log P

4.09

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

9.62

极化表面积

58.92

极化性

34.65

摩尔折射率

93.35

LOG S

-4.33

数据来源

名称和标识

IUPAC标准名

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传统名

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

别名

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

名称和标识

数据登录号

PubChem CID

Chemspider ID

CHEMBL

维基百科标题

CAS号

Beilstein号

MDL号

PubChem SID

CompTox数据库

KNApSAcK数据库

LIPID MAPS Instance

PubMed文献链接

HMDB数据库

MetaboLights数据库

SureChEMBL数据库

Reaxys Registry

CHEBI ID

PDB数据库

ACToR数据库

KEGG ID

数据登录号

化合物性质

药理学性质

生物活性机理

Melanogenesis inhibitor

Tyrosinase inhibitor

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

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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,

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

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

• 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.

• 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

• 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.

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

• 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.

• 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,

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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

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传统名

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

别名

数据登录号

PubChem CID

Chemspider ID

CHEMBL

维基百科标题

CAS号

Beilstein号

MDL号

PubChem SID

CompTox数据库

KNApSAcK数据库

LIPID MAPS Instance

PubMed文献链接

HMDB数据库

MetaboLights数据库

SureChEMBL数据库

Reaxys Registry

CHEBI ID

PDB数据库

ACToR数据库

KEGG ID

描述信息

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.

参考文献

PubChem文献

数据源提供

• 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,

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

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

• 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.

• 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

• 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.

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

• 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,

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

生物活性

PubChem BioAssay

化合物性质

药理学性质

生物活性机理

Melanogenesis inhibitor

Tyrosinase inhibitor

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

化合物信息

ID:127561