Glycyrrhyzin (YMDB01703)

Identification
YMDB IDYMDB01703
NameGlycyrrhyzin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionGlycyrrhizic acid, also known as glycyrrhizin, 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. Glycyrrhizic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Acid, glycyrrhizic
  • Acid, glycyrrhizinic
  • Diammonium glycyrrhizinate
  • Dipotassium glycyrrhizinate
  • e958
  • Glycyrrhetinate
  • Glycyrrhetinic acid
  • Glycyrrhizate
  • Glycyrrhizate, zinc
  • Glycyrrhizin
  • Glycyrrhizinate
  • Glycyrrhizinate, diammonium
  • Glycyrrhizinate, dipotassium
  • Glycyrrhizinic acid
  • Zinc glycyrrhizate
  • (3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
  • (3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronate
  • (3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid
  • (3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronate
  • (3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronate
  • (3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
  • Glycyrrhizic acid
CAS numberNot Available
WeightAverage: 822.9321
Monoisotopic: 822.403785936
InChI KeyLPLVUJXQOOQHMX-QWBHMCJMSA-N
InChIInChI=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
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 IUPAC Nameglycyrrhizin
Chemical FormulaC42H62O16
SMILESCC1(C)[C@H](CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O)O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)=O
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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-4ce2b1a1894e31a4b583JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-05cf6f9c95233e0b6093JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-b7273d4a3c7ac5053507JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000000090-380d12d32657ccb592bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0102000090-bed09978385e89f7fa03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0101000090-e2103026d03012f4386bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0002000090-301b760e1a43241eb03dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0202000090-f5911cc6b21dd8fa08faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0002000090-8620dc60deae22ab4b96JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-f5c5cfd754bfd69139d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-ec1596ab8cbd06c136c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0w29-0709000000-3a40dbcd4a9e24a4e64aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0000000090-00d5155c760746cee29cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0001000090-5fd4d3fb6b71940d3e21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0fk9-0104000090-35df1ca6b0cc93c2681bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0uk9-0309000050-ce67083e8ed48da875b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-0000000090-8cd630bf15ce35555075JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fk9-0000702090-b0ba25c87ff68dd3b767JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0000901000-57104f23e3197f427a1dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kor-0100906240-38e22c4d3b2d92e7e509JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0100903000-e9c85f0d5255892714b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-0302901000-45e1b08ddcbdc4c5de1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g29-1600827960-582446907b46f4d6cbf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-1700924300-bf530faa06e887dd67f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-3800911000-853ddaa12db092f48627JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15939
HMDB IDNot Available
Pubchem Compound ID14982
Kegg IDNot Available
ChemSpider ID23089588
FOODB IDNot Available
Wikipedia IDGlycyrrhizin
BioCyc IDNot Available