(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 ID: 72945
• Molecular Formular: C42H62O16
• Molecular Mass: 822.93208
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Synonyms: 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

Database IDs

• CAS Number: 1405-86-3
• EC Number: 215-785-7
• PubChem SID: 162037865
• PubChem CID: 14982
• CHEBI ID: 15939
• ATC CODE: A05BA08
• CHEMBL: 606553
• Chemspider ID: 14263
• Unique Ingredient Identifier: 6FO62043WK
• Wikipedia Title: Glycyrrhizin

CALCULATED PROPERTIES

• Acid pKa: 2.961005
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -2.329018
• LogD (pH = 7.4): -6.5692225
• Log P: 3.1302059
• Molar Refractivity: 198.8299 cm^3
• Polarizability: 80.55014 Å^3
• Polar Surface Area: 267.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

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.

REFERENCES

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