Glycyrrhizic acid, Antiviral agent

Key facts

CAS number

1405-86-3

Purity

>98%

Form

Solid

form

Source

Glycyrrhiza glabra

Molecular weight

822.9 Da

Molecular formula

C₄₂H₆₂O₁₆

PubChem

53312460

Nature

Native

Solubility

Soluble in water to 20 mM

Soluble in DMSO to 100 mM

Soluble in ethanol to 100 mM

Biochemical name

(3S,4S,5R,6R)-6-[(2S,3R,4S,5S)-2-[[(3S,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

Biological description

Antiviral agent. 11β-hydroxysteroid dehydrogenase inhibitior. Increases glyoxalase-1 activity and expression. Shows anti-inflammatory, antiviral, antimicrobial, antioxidative, anticancer, immunomodulatory, hepatoprotective and cardioprotective effects in vivo. Orally active.

Canonical smiles

CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C

Isomeric smiles

C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C(C5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@@H]6[C@@H]([C@H]([C@@H](C(O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](C(O7)C(=O)O)O)O)O)C)(C)C(=O)O

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-ZOXVGBFRSA-N

IUPAC Name

(3S,4S,5R,6R)-6-[(2S,3R,4S,5S)-2-[[(3S,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