(2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

• ChemBase编号: 72945
• 分子式: C42H62O16
• 平均质量: 822.93208
• 单一同位素质量: 822.4037859
• 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(=O)O)C)C)C)C)C)(C)C)O[C@H]1O[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)C(=O)O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C
• InChI: InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
• InChIKey: LPLVUJXQOOQHMX-QWBHMCJMSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-2-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: glyzyrrhizin; (2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-2-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: Glycyrrhizic acid; (3β,20β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-Glucopyranuronosyl-α-D-glucopyranosiduronic Acid; 18β-Glycyrrhizic Acid; 18β-Glycyrrhizinic Acid; Glycyron; Glycyrrhetinic Acid Glycoside; NSC 167409; NSC 234419; Potenlini; β-Glycyrrhizin; Glycyrrhizin; Glycyrrhizinic acid; Glycyrrhizic acid; Glycyrrhizin

登记号

• CAS号: 1405-86-3
• EC号: 215-785-7
• PubChem SID: 162037865
• PubChem CID: 14982
• CHEBI ID: 15939
• ATC码: A05BA08
• CHEMBL: 606553
• Chemspider ID: 14263
• 美国药典/FDA物质标识码: 6FO62043WK
• 维基百科标题: Glycyrrhizin

理论计算性质

• Acid pKa: 2.961005
• 质子受体: 16
• 质子供体: 8
• LogD (pH = 5.5): -2.329018
• LogD (pH = 7.4): -6.5692225
• Log P: 3.1302059
• 摩尔折射率: 198.8299 cm^3
• 极化性: 80.55014 Å^3
• 极化表面积: 267.04 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

安全信息

• 保存条件: -20°C

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2302

Research Area: Inflammation
Biological Activity:
Glycyrrhizic acid is a widely used anti-inflammatory agent isolated from the licorice root. It is metabolized to glycyrrhetic acid, which inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the metabolism of corticosteroids. Therefore, glycyrrhizic acid, which is the main and sweet component of licorice, has been investigated for its ability to cause hypermineralocorticoidism with sodium retention and potassium loss, edema, increased blood pressure, as well as depression of the renin-angiotensin-aldosterone system. [1]

Toronto Research Chemicals - G735150

Glycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.

参考文献

• http://en.wikipedia.org/wiki/Glycyrrhizin
• Marsh, L., et al.: Biochem. J., 63, 9 (1956)
• Kitagawa, et al.: Chem. Pharm. Bull., 36, 3710 (1956)