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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:00 UTC
Update Date2018-03-12 22:03:47 UTC
HMDB IDHMDB0029843
Secondary Accession Numbers
  • HMDB29843
Metabolite Identification
Common NameGlycyrrhizin
DescriptionGlycyrrhizin, also known as glycyram or dermacrin, 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. Glycyrrhizin exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, glycyrrhizin is primarily located in the membrane (predicted from logP) and cytoplasm. Glycyrrhizin is a mild and spicy tasting compound that can be found in herbs and spices and root vegetables. This makes glycyrrhizin a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
beta-GlycyrrhizinHMDB
DermacrinHMDB
GlycyramHMDB
GlycyronHMDB
Glycyrrhetic acid 3-O-[b-D-glucuronopyranosyl-(1->2)-a-D-glucuronopyranoside]HMDB
GlycyrrhitinHMDB
Glycyrrhizin, janHMDB
GlycyrrhizinateHMDB
Glycyrrhizinic acidHMDB
GlycyrrizinHMDB
Glycyrrhizate, zincMeSH
Acid, glycyrrhizinicMeSH
Dipotassium glycyrrhizinateMeSH
Glycyrrhizinate, diammoniumMeSH
Glycyrrhizinate, dipotassiumMeSH
Zinc glycyrrhizateMeSH
Acid, glycyrrhizicMeSH
Glycyrrhizic acidMeSH
Diammonium glycyrrhizinateMeSH
Chemical FormulaC42H62O16
Average Molecular Weight822.9321
Monoisotopic Molecular Weight822.403785936
IUPAC Name5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-[(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]-3,4-dihydroxyoxane-2-carboxylic acid
Traditional Nameammonium glycyrrhizate
CAS Registry Number1405-86-3
SMILES
CC1(C)C(CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(C)CCC12C)C(O)=O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O)C(O)=O
InChI Identifier
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)
InChI KeyLPLVUJXQOOQHMX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.80Not 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
Polarizability86.97 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009001000-76ff4bd04d18861bcec1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-ad9d816c97b0b6260b22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0000509430-04def68d9fdc81858040View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-ed61a3fba8a67934b5b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-0bd1a08a534d106c473dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0000109000-9621e9e32834e62d1b98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0000039000-8ffe627b0abc1703ebf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w9a-0001906310-070e8a42beae3e32b9eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-b15e55841197b74676f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0000109000-d1f369e2c1009923d602View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0000039000-ff48b9c18064290532dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pk9-0100906250-8be353527a95cffaba8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmi-0100904000-f24b016e7c30fe139718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-0302901000-8eb7f40c63ac56312173View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g29-1500827970-ab2b4b8ca046fbd429d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-1700914310-0fc211d45115fc0c16e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-3700911000-213b48473924464dafccView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001060
KNApSAcK IDNot Available
Chemspider ID3375
KEGG Compound IDC02284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlycyrrhizin
METLIN IDNot Available
PubChem Compound3495
PDB IDNot Available
ChEBI ID15939
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.