Glycyrrhizin (CHEM019379)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:03:48 UTC
Update Date2016-11-09 01:15:59 UTC
Accession NumberCHEM019379
Identification
Common NameGlycyrrhizin
ClassSmall Molecule
DescriptionA triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-4ce2b1a1894e31a4b583Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-05cf6f9c95233e0b6093Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-b7273d4a3c7ac5053507Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-380d12d32657ccb592bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0102000090-bed09978385e89f7fa03Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0101000090-e2103026d03012f4386bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0002000090-301b760e1a43241eb03dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0202000090-f5911cc6b21dd8fa08faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0002000090-8620dc60deae22ab4b96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-f5c5cfd754bfd69139d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-ec1596ab8cbd06c136c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0w29-0709000000-3a40dbcd4a9e24a4e64aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-00d5155c760746cee29cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0001000090-5fd4d3fb6b71940d3e21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0fk9-0104000090-35df1ca6b0cc93c2681bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0uk9-0309000050-ce67083e8ed48da875b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-0000000090-8cd630bf15ce35555075Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fk9-0000702090-b0ba25c87ff68dd3b767Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0000901000-57104f23e3197f427a1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kor-0100906240-38e22c4d3b2d92e7e509Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0100903000-e9c85f0d5255892714b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-0302901000-45e1b08ddcbdc4c5de1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g29-1600827960-582446907b46f4d6cbf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-1700924300-bf530faa06e887dd67f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-3800911000-853ddaa12db092f48627Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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