ChemFOnt: Showing chemical card for Glycyrrhetic acid (CFc000336734)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:03 UTC

Chemfont ID

CFc000336734

Molecule Identification

Common Name

Glycyrrhetic acid

Definition

Aglycone from licorice (Glycyrrhiza glabra) Glycyrrhetinic acid 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 is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. Glycyrrhetic acid is found in tea and herbs and spices.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
18beta-Glycyrrhetic acid	ChEBI
Glycyrrhetinic acid	Kegg
Hidermart	Kegg
18b-Glycyrrhetate	Generator
18b-Glycyrrhetic acid	Generator
18beta-Glycyrrhetate	Generator
18Β-glycyrrhetate	Generator
18Β-glycyrrhetic acid	Generator
Glycyrrhetinate	Generator
Enoxolone	ChEBI
Acid, glycyrrhetinic	MeSH
Acid, glycyrrhetic	MeSH
Glycyrrhetic acid	MeSH
Rhetinic acid	MeSH
Acid, uralenic	MeSH
12, Po	MeSH
Uralenic acid	MeSH
Acid, rhetinic	MeSH
Po 12	MeSH
Glyciram	MeSH
Glycyram	MeSH
Jintan	MeSH
Arthrodont	MeSH

Chemical Formula

C₃₀H₄₆O₄

Average Molecular Weight

470.694

Monoisotopic Molecular Weight

470.339609961

IUPAC Name

(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

Traditional Name

jintan

CAS Registry Number

471-53-4

SMILES

[H][C@]1(O)CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])C(=O)C=C2[C@]4([H])C[C@](C)(CC[C@]4(C)CC[C@@]32C)C(O)=O)C1(C)C

InChI Identifier

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

InChI Key

MPDGHEJMBKOTSU-YKLVYJNSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:30853 )
pentacyclic triterpenoid (CHEBI:30853 )
cyclic terpene ketone (CHEBI:30853 )
Oleananes (C02283 )
Oleanane triterpenoids (LMPR0106150014 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB11628)

Food

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.45	ALOGPS
logP	6.03	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.27 m³·mol⁻¹	ChemAxon
Polarizability	55.17 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon