CAS 471-53-4|Enoxolone|jintan|(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carbox...

基本信息

化学结构

分子式

C₃₀H₄₆O₄

分子量

470.68384

精确质量

470.33960995

电荷

InChI

InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1

InChIKey

MPDGHEJMBKOTSU-YKLVYJNSSA-N

Canonic Smiles

O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O

Isomeric Smiles

C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1=O)[C@H]1[C@@](CC2)(CC[C@](C1)(C)C(=O)O)C)C)C)C)(C)C)O

计算属性

JChem

Acid pKa

4.4443316

质子受体

质子供体

LogD (pH = 5.5)

4.940498

LogD (pH = 7.4)

3.1778886

Log P

6.031328

摩尔折射率

134.2685

极化性

53.29785

极化表面积

74.6

可自由旋转的化学键

里宾斯基五规则

false

数据来源

名称和标识

别名

Enoxolone(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid18β-Glycyrrhetinic acidGlycyrrhetin3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acidGlycyrrhetinic acid3β-Hydroxy-11-oxoolean-12-en-30-olic acid甘草次酸18β-甘草次酸EnoxoloneArthrodontUralenic acidGlycyrrhetinateSTX 352α-Glycyrrhetinic Acid3β-Hydroxy-11-oxo-olean-12-en-30-oic Acid18β-Glycyrrhetinic AcidGlycyrrhetic Acid(3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic AcidNSC 35347PO 12Subglycyrrhelinic Acid18β-Glycyrrhetic AcidGM 1658EnoxoloneGlycyrrhetinic acidGlycyrrhetic acidBiosoneRhetinic acidBiogastrone acid

IUPAC传统名

jintan (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

IUPAC标准名

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

名称和标识

数据登录号

CAS号

Chemspider ID

ATC码

PubChem CID

CHEBI ID

CHEMBL

维基百科标题

PubChem SID

2487337024895033162037861

EC号

207-444-6

MDL号

MFCD00003706

Beilstein号

2229654

数据登录号

化合物性质

药理学性质

相关基因信息

human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117)

生物活性机理

Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro

Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion

Calcium-mobilizer in P815 cells in-vitro

理化性质

熔点

292-295 °C(lit.)

比旋光度

[α]22/D +170.0°, c = 1 in chloroform

[α]20/D +165±3°, c = 1% in chloroform

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

Selleck Chemicals

S2296

Research Area: Inflammation
Biological Activity:
Enoxolone is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice.It inhibits the enzymes (15-hydroxyprostaglandin dehydrogenase and delta-13-prostaglandin) that metabolize the prostaglandins PGE-2 and PGF-2α to their respective 15-keto-13,14-dihydro metabolites which are inactive. This causes an increased level of prostaglandins in the digestive system. Prostaglandins inhibit gastric secretion but stimulate pancreatic secretion and mucous secretion in the intestines and markedly increase intestinal motility. [1]

Wikipedia

Glycyrrhetinic_acid

Sigma Aldrich

G10105

包装
10, 25 g in poly bottle

TRC

G735000

An anti-inflammatory (topical).

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Glycyrrhetinic_acid

• Deschesnes, R., et al.: J. Pharmacol. Exp. Ther., 320, 853 (1987)

• Yamaguchi, H., et al.: Biol. Pharm. Bull., 31, 1008 (1987)

• Carmichael, J., et al.: Cancer Res., 47, 943 (1987)

• Robson, J.M. et al., Carbenoxolone Sodium, Orig. Pap. Discuss. Group Meet., Butterworth, London, 1969, (rev)

• Tolstikov, G.A. et al., Khim. Prir. Soedin., 1985, 21, 645; Chem. Nat. Compd. (Engl. Transl.), 1985, 21, 605, (cmr)

• Sakano, K. et al., Agric. Biol. Chem., 1986, 50, 763, (deriv)

• Sandiya, R. et al., J. Het. Chem., 1984, 21, 845, (isol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 758; 873

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GIE000; BGD000; GIEO5O; CBO500

• U.K. Pat., 1960, 843 133; CA, 55, 2027i, (Carbenoxolone)

• Beaton, J.M. et al., J.C.S., 1955, 3126, (synth)

• Canonica, L. et al., Gazz. Chim. Ital., 1967, 97, 1347; 1968, 98, 602, (Glycyrrhetol)

• Wahlberg, I. et al., Acta Chem. Scand., 1971, 25, 3192, (ms)

• Mer, J., Am. Perfum. Aromat., 1959, 74, 39, (isol)

• Kanaoka, M. et al., Chem. Pharm. Bull., 1988, 36, 3264, (synth)

• Saito, S. et al., Chem. Pharm. Bull., 1994, 42, 1016, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1057D, (ir)

• Budzikiewicz, H. et al., J.A.C.S., 1963, 85, 3688, (ms)

• Murav'ev, I.A. et al., CA, 1966, 69, 44029v, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 596A, (nmr)

• Witz, P. et al., Bull. Soc. Chim. Fr., 1963, 1101, (cd)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7889; 8042, (synonyms)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

jintan (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

IUPAC标准名

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

数据登录号

CAS号

Chemspider ID

ATC码

PubChem CID

CHEBI ID

CHEMBL