Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2019-11-26 02:55:51 UTC
Primary IDFDB001060
Secondary Accession Numbers
  • FDB018788
Chemical Information
FooDB NameGlycyrrhizin
DescriptionGlycyrrhizin 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. Based on a literature review a small amount of articles have been published on Glycyrrhizin.
CAS Number1405-86-3
Structure
Thumb
Synonyms
SynonymSource
beta-GlycyrrhizinHMDB
DermacrinHMDB
GlycyramHMDB
GlycyronHMDB
Glycyrrhetic acid 3-O-[b-D-glucuronopyranosyl-(1->2)-a-D-glucuronopyranoside]HMDB
GlycyrrhitinHMDB
Glycyrrhizin, janHMDB
GlycyrrhizinateHMDB
Glycyrrhizinic acidHMDB, MeSH
GlycyrrizinHMDB
Glycyrrhizate, zincMeSH, HMDB
Acid, glycyrrhizinicMeSH, HMDB
Dipotassium glycyrrhizinateMeSH, HMDB
Glycyrrhizinate, diammoniumMeSH, HMDB
Glycyrrhizinate, dipotassiumMeSH, HMDB
Zinc glycyrrhizateMeSH, HMDB
Acid, glycyrrhizicMeSH, HMDB
Glycyrrhizic acidMeSH, HMDB
Diammonium glycyrrhizinateMeSH, HMDB
6-({6-carboxy-2-[(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]-4,5-dihydroxyoxan-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
GlycyrrhizinMeSH
Beta-glycyrrhizinbiospider
Glycyrrhizin, JANdb_source
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H62O16
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
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)
InChI KeyLPLVUJXQOOQHMX-UHFFFAOYSA-N
Isomeric SMILESCC1(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
Average Molecular Weight822.9321
Monoisotopic Molecular Weight822.403785936
Classification
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.30%; H 7.59%; O 31.11%DFC
Melting PointMp 220 approx.°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.80SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]17D +46.2 (c, 1.5 in EtOH)DFC
Spectroscopic UV Data[neutral] lmax 249 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009001000-76ff4bd04d18861bcec1Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-ad9d816c97b0b6260b22Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0000509430-04def68d9fdc81858040Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-ed61a3fba8a67934b5b4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-0bd1a08a534d106c473dSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0000109000-9621e9e32834e62d1b98Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0000039000-8ffe627b0abc1703ebf9Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w9a-0001906310-070e8a42beae3e32b9eeSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00kr-0000902000-b15e55841197b74676f3Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0000109000-d1f369e2c1009923d602Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0000039000-ff48b9c18064290532dfSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ikc-2902000000-399923f2f0b32e08f212Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000900000-8aab5d58fbdb2b9cd0b1Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ikc-2902000000-233d95340032c864fb3bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000902020-217813344bd06b878080Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0001000090-061037d23e7a7de1013fSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0000000090-a45ac1fef7312591606fSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ur0-0000902080-cace6a504d72d3e68c21Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000901000-73210eda76448fb2f333Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pk9-0100906250-8be353527a95cffaba8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmi-0100904000-f24b016e7c30fe139718Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-0302901000-8eb7f40c63ac56312173Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g29-1500827970-ab2b4b8ca046fbd429d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-1700914310-0fc211d45115fc0c16e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-3700911000-213b48473924464dafccSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC02284
Pubchem Compound ID14982
Pubchem Substance IDNot Available
ChEBI ID15939
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBRB99-M:BRB99-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003522
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1032161
SuperScent IDNot Available
Wikipedia IDGlycyrrhizin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference