Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2019-11-27 17:04:20 UTC
Primary IDFDB001060
Secondary Accession Numbers
  • FDB018788
Chemical Information
FooDB NameGlycyrrhizin
DescriptionGlycyrrhizin, also known as dermacrin or glycyram, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa).
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
GlycyrrizinHMDB
Glycyrrhizate, zincHMDB
Acid, glycyrrhizinicHMDB
Dipotassium glycyrrhizinateHMDB
Glycyrrhizinate, diammoniumHMDB
Glycyrrhizinate, dipotassiumHMDB
Zinc glycyrrhizateHMDB
Acid, glycyrrhizicHMDB
Glycyrrhizic acidHMDB
Diammonium glycyrrhizinateHMDB
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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
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, 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
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
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