Ammonium glycyrrhizinate trihydrateProduct ingredient for Glycyrrhizic acid

Name

Ammonium glycyrrhizinate trihydrate

Drug Entry

Glycyrrhizic acid

Glycyrrhizic acid is extracted from the root of the licorice plant; Glycyrrhiza glabra.¹¹ It is a triterpene glycoside with glycyrrhetinic acid that possesses a wide range of pharmacological and biological activities. When extracted from the plant, it can be obtained in the form of ammonium glycyrrhizin and mono-ammonium glycyrrhizin.⁸ Glycyrrhizic acid has been developed in Japan and China as a hepatoprotective drug in cases of chronic hepatitis.¹ From January 2014, glycyrrhizic acid as part of the licorice extract was approved by the FDA as an existing food sweetener.¹² It was approved by Health Canada to be used in over-the-counter products but all the products are currently on the status canceled post marketed.¹⁰

See full entry for Glycyrrhizic acid

Accession Number

DBSALT002692

Structure

Similar Structures

Synonyms

Glycyrrhizic acid ammonium salt trihydrate

UNII

78NEL3149I

CAS Number

911217-00-0

Weight

Average: 894.018
Monoisotopic: 893.46202907

Chemical Formula

C₄₂H₇₁NO₁₉

InChI Key

RSPXVECNDMCBGQ-YMYWBCTMSA-N

InChI

InChI=1S/C42H62O16.H3N.3H2O/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);1H3;3*1H2/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;;;;/m0..../s1

IUPAC Name

ammonium (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-carboxylate trihydrate

SMILES

[NH4+].O.O.O.[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C([O-])=O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

External Links

ChemSpider: 2006388
ChEMBL: CHEMBL3561931

Predicted Properties

Property	Value	Source
Water Solubility	0.0427 mg/mL	ALOGPS
logP	2.84	ALOGPS
logP	3.13	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	2.96	Chemaxon
pKa (Strongest Basic)	-3.7	Chemaxon
Physiological Charge	-3	Chemaxon
Hydrogen Acceptor Count	16	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	269.87 Å²	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	209.67 m³·mol^-1	Chemaxon
Polarizability	85.75 Å³	Chemaxon
Number of Rings	7	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Ammonium glycyrrhizinate trihydrateProduct ingredient for Glycyrrhizic acid

Structure for Ammonium glycyrrhizinate trihydrate (DBSALT002692)