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Substance Name: Glycyrrhizin [JAN]
RN: 1405-86-3
UNII: 6FO62043WK
InChIKey: LPLVUJXQOOQHMX-QWBHMCJMSA-N

Note

  • A widely used anti-inflammatory agent isolated from the licorice root. It is metabolized to GLYCYRRHETINIC ACID, which inhibits 11-BETA-HYDROXYSTEROID DEHYDROGENASES 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.

Molecular Formula

  • C42-H62-O16

Molecular Weight

  • 822.936
 

Classification Codes

  • Anti-Inflammatory Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
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Names and Synonyms

Name of Substance

  • (3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
  • alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-
  • Glycyrrhizic acid
  • Glycyrrhizin
  • Glycyrrhizin [JAN]
  • Glycyrrhizinic acid

MeSH Heading

  • Glycyrrhizic acid

Synonyms

  • (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
  • 18-beta-Glycyrrhizic acid
  • 18beta-Glycyrrhizic acid
  • 20beta-Carboxy-11-oxo-30-norolean-12-en-3beta-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
  • 4-18-00-05156 (Beilstein Handbook Reference)
  • alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuron osyl-
  • beta-Glycyrrhizin
  • BRN 0077922
  • CCRIS 8444
  • EINECS 215-785-7
  • Glizigen
  • Glycyron
  • Glycyrrhetinic acid glycoside
  • Glycyrrhizic acid
  • Glycyrrhizin
  • Glycyrrhizinic acid
  • Glycyrrizin
  • HSDB 496
  • Liquorice
  • Neo-Umor
  • NSC 167409
  • NSC 234419
  • NSC 2800
  • Rizinsan K2 A2 (free acid)
  • UNII-6FO62043WK

Systematic Names

  • 20beta-Carboxy-11-oxo-30-norolean-12-en-3beta-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
  • alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-
  • Glycyrrhizic acid
  • Glycyrrhizinic acid

Registry Numbers

CAS Registry Number

  • 1405-86-3

FDA UNII

  • 6FO62043WK

Other Registry Numbers

  • 1208112-19-9
  • 139014-59-8
  • 18933-02-3
  • 31261-47-9
  • 47897-45-0
  • 47897-48-3
  • 70055-50-4
  • 79165-07-4
  • 947339-02-8

System Generated Number

  • 0001405863

Structure Descriptors

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

Smiles

C1([C@H]2[C@@]([C@@]3(C([C@H]4[C@@](CC[C@@](C4)(C(O)=O)C)(C)CC3)=C1)C)(CC[C@@H]1[C@@]2(CC[C@@H](C1(C)C)O[C@@H]1[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)O)C(O)=O)[C@H]([C@H](O)[C@H](O1)C(O)=O)O)C)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5571ug/kg/3D- (5.571mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION Toxicologist. Vol. 54, Pg. 109, 2000.
human TDLo oral 280mg/kg/4W (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) British Medical Journal. Vol. 1, Pg. 488, 1977.
man TDLo oral 662mg/kg/1Y-I (662mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Internal Medicine. Vol. 31, Pg. 708, 1992.
mouse LD50 intravenous 589mg/kg (589mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 28, Pg. 215, 1993.
mouse LD50 oral 4320mg/kg (4320mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 28, Pg. 215, 1993.
mouse LDLo intraperitoneal 1gm/kg (1000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LD intravenous > 300mg/kg (300mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LDLo intraperitoneal 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LDLo oral 3gm/kg (3000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 220 dec deg C   EXP
log P (octanol-water) 2.8 (none)   EXP
Water Solubility 0.053 mg/L 25 EST
Vapor Pressure 5.22E-34 mm Hg 25 EST
Henry's Law Constant 1.23E-35 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.30E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.