Glycyrrhizin (CED0002518)

Record Information
Version1.0
Creation Date2016-05-22 06:03:48 UTC
Update Date2026-05-14 19:36:47 UTC
Accession NumberCHEM019379
Identification
Common NameGlycyrrhizin
ClassSmall Molecule
Description
Glycyrrhizin (C42H62O16) is a chemical compound used industrially as a humectant, a softener and conditioner, and a flavouring and nutrient. Glycyrrhizin belongs to the terpene glycosides, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 822.94 g/mol, Glycyrrhizin is a heavy molecule. The compound is found in or released from 24 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with lipotropics and liver therapy. Other sources include electrical and electronic equipment such as hybrid capacitors, video games, auxiliary devices, electrically stimulated smoking devices, and fixed capacitors and their manufacture. It is also present in household cleaning and consumer products, including pipe accessories, non electric simulated smoking devices, bleaching agents, cigar cigarettes, other smoking requisites, and four additional sources. Furthermore, it is found in food, food processing, and cookware, specifically in the preparation of vinegar, preparation of wine or sparkling wine, fermentation processes for beer, molasses and treatment of molasses, agglomerated sugar products, and four more. Recorded exposure routes include oral, dental, cutaneous, and topical. Glycyrrhizin interacts with six recorded protein targets. It acts as an antagonist/antagonist and functions as an inhibitor, inducer, or translocation inhibitor of 11-beta-hydroxysteroid dehydrogenase 1 (HSD11B1). Additionally, it targets the nuclear factor NF-kappa-B p105 subunit (NFKB1), tumor necrosis factor (TNF), caspase-3 (CASP3), and two other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acidChEBI
GlycyrrhizinChEBI
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronateGenerator
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acidGenerator
(3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronateGenerator
(3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronateGenerator
(3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acidGenerator
GlycyrrhizateGenerator
Glycyrrhizic acidChEBI
Diammonium glycyrrhizinateMeSH
Zinc glycyrrhizateMeSH
Acid, glycyrrhizicMeSH
Glycyrrhizinic acidMeSH
Acid, glycyrrhizinicMeSH
Dipotassium glycyrrhizinateMeSH
Glycyrrhizate, zincMeSH
Glycyrrhizinate, diammoniumMeSH
Glycyrrhizinate, dipotassiumMeSH
Chemical FormulaC42H62O16
Average Molecular Mass822.942 g/mol
Monoisotopic Mass822.404 g/mol
CAS Registry Number1405-86-3
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
Traditional Nameglycyrrhizin
SMILES[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
InChI IdentifierInChI=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
InChI KeyLPLVUJXQOOQHMX-QWBHMCJMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Cyclohexenone
  • Pyran
  • Oxane
  • Hydroxy acid
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP2.78ALOGPS
logP3.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area267.04 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity198.83 m³·mol⁻¹ChemAxon
Polarizability86.35 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-4ce2b1a1894e31a4b583Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-05cf6f9c95233e0b6093Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-b7273d4a3c7ac5053507Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-380d12d32657ccb592bcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0102000090-bed09978385e89f7fa03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0101000090-e2103026d03012f4386bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0002000090-301b760e1a43241eb03dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0202000090-f5911cc6b21dd8fa08faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0002000090-8620dc60deae22ab4b96Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-f5c5cfd754bfd69139d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-ec1596ab8cbd06c136c1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0w29-0709000000-3a40dbcd4a9e24a4e64aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-00d5155c760746cee29cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0001000090-5fd4d3fb6b71940d3e21Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-0104000090-35df1ca6b0cc93c2681bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0309000050-ce67083e8ed48da875b9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006x-0000000090-8cd630bf15ce35555075Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-0000702090-b0ba25c87ff68dd3b767Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000901000-57104f23e3197f427a1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000900000-537381840e9d1d1c4253Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000900000-ed766c3b16a4efad6b09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000901000-115bc1eeeaff2bc6cf94Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000901000-22da39f178b78eb4cafeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kor-0100906240-38e22c4d3b2d92e7e509Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-0100903000-e9c85f0d5255892714b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-0302901000-45e1b08ddcbdc4c5de1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0g29-1600827960-582446907b46f4d6cbf7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016s-1700924300-bf530faa06e887dd67f6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-3800911000-853ddaa12db092f48627Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
251Liver therapy, lipotropicsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier organic anion transporter family member 1B2Q9QZX8Rattus norvegicusPredicted (SEA)0.0778492
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)0.467095
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase type 2P80365HumansPredicted (SEA)0.467095
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P50172Mus musculusPredicted (SEA)0.778492
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)7.39568
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)0.389246
Click to view 3D structureATP-binding cassette sub-family C member 2Q63120Rattus norvegicusPredicted (SEA)0.155698
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)13.3122
Tyrosine-protein phosphatase non-receptor type 2 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 2P17706HumansPredicted (SEA)7.16213
Click to view 3D structurePannexin-1Q9JIP4Mus musculusPredicted (SEA)0.311397
FUN14 domain-containing protein 1 structureClick to view 3D structureFUN14 domain-containing protein 1Q8IVP5HumansPredicted (SEA)3.65891
Prostaglandin E synthase structureClick to view 3D structureProstaglandin E synthaseO14684HumansPredicted (SEA)15.9591
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)19.8516
Click to view 3D structureEndopolygalactyuronaseP79074Chondrostereum purpureumPredicted (SEA)0.233548
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)44.8412
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)17.4382
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)152.584
Click to view 3D structureProteaseQ9YQ12Human immunodeficiency virus 1Predicted (SEA)40.248
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase type 2P50233Rattus norvegicusPredicted (SEA)0.700643
Click to view 3D structureCytochrome P450 2C11P08683RatPredicted (SEA)0.856341
Click to view 3D structureL-ornithine N(5)-monooxygenaseE9QYP0Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSCA1100) (Aspergillus fumigatus)Predicted (SEA)0.856341
Click to view 3D structureHemagglutininB4URE7Influenza A virusPredicted (SEA)3.42537
Click to view 3D structureLactoylglutathione lyaseQ9CPU0Mus musculusPredicted (SEA)0.622794
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)155.854
Cholesteryl ester transfer protein structureClick to view 3D structureCholesteryl ester transfer proteinP11597HumansPredicted (SEA)10.4318
Concentrations
Not Available
External Links
DrugBank IDDB13751
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDGLYCYRRHIZINATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlycyrrhizin
Chemspider IDNot Available
ChEBI ID15939
PubChem Compound ID14982
Kegg Compound IDNot Available
YMDB IDYMDB01703
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11282481
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15013279
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24497916