precursor metabolite

Showing entry for Glycyrrhetinic acid

Identification

PhytoHub ID
PHUB000170
Name
Glycyrrhetinic acid
Systematic Name
Not Available
Synonyms
  • 18β-glycyrrhetinic acid
  • Glycyrrhetic acid
  • Glycyrrhetic acid (alpha-)
  • Glycyrrhetin
CAS Number
Not Available
Average Mass
470.694
Monoisotopic Mass
470.339609961
Chemical Formula
C30H46O4
IUPAC Name
(2S,4aS,6aS,6bR,10S,12aS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
InChI Key
MPDGHEJMBKOTSU-WFJWTYAKSA-N
InChI Identifier
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19?,21?,22-,23?,26+,27-,28-,29+,30+/m0/s1
SMILES
CC1(C)[C@@H](O)CC[C@@]2(C)C1CC[C@]1(C)C2C(=O)C=C2C3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.72e-03 g/l
LogS (ALOGPS)
-5.44
LogP (ALOGPS)
5.45
Hydrogen Acceptors
4
Hydrogen Donors
2
Rotatable Bond Count
1
Polar Surface Area
74.6
Refractivity
134.2685
Polarizability
55.3864348876561
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-0.8351069321304386
pKa (strongest acidic)
4.44433188134718
Number of Rings
5
Rule of Five
No
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Terpenoids
Class
Triterpenoids
Sub-class
Saponins

Taxonomy as Metabolite

Metabolite Family
Terpenoid metabolites
Metabolite Class
Triterpenoid metabolites
Metabolite Sub-class
Saponins (parent, host and microbial metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
GlycyrrhizinTerpenoidsTriterpenoidsSaponinsShow Food Phytochemical
Glycyrrhetinic acidTerpenoidsTriterpenoidsSaponinsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Triterpenoids
Direct Parent Name
Triterpenoids
Alternative Parent Names
["Carboxylic acids", "Cyclic alcohols and derivatives", "Cyclohexenones", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["Alcohol", "Aliphatic homopolycyclic compound", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cyclic alcohol", "Cyclohexenone", "Hydrocarbon derivative", "Ketone", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Secondary alcohol", "Triterpenoid"]

Spectra from Phytohub

Spectrum TypeInstrument TypeTechnologyIon ModeCollision EnergyView
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0EiNot AvailableView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative10VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative20VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative50VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative40VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegativeVView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative10VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative30VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative10VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative20VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative50VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative40VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegativeVView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative10VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative30VView Spectrum
LC-MS/MSLC-ESI-qTofFrom GNPS LibraryPositiveVView Spectrum
LC-MS/MSLC-ESI-QFTinstrument=Q Exactive Plus Orbitrap Thermo ScientificnegativeVView Spectrum
LC-MS/MSLC-ESI-QFTinstrument=Q Exactive Plus Orbitrap Thermo ScientificnegativeVView Spectrum
LC-MS/MSLC-ESI-QFTinstrument=Q Exactive Plus Orbitrap Thermo ScientificnegativeVView Spectrum
LC-MS/MSLC-ESI-QFTinstrument=Q Exactive Plus Orbitrap Thermo ScientificnegativeVView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive40VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative40VView Spectrum

Food Sources

NameGroup
LiquoriceConfectioneries and desserts PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
GlycyrrhizinLiquoriceConfectioneries and desserts PublicationsShow
Glycyrrhetinic acidLiquoriceConfectioneries and desserts PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Glycyrrhetinic acid Glycyrrhetinic acidhumanplasma, urineunchanged3h-5h5-20µmol/L<1%C30H46O4470.339609961 Detailed Intervention Studies Publications
Glycyrrhizin Glycyrrhetinic acidhuman ratbile, plasma, urinegut microbiota metabolite12h-24h<20 nmol/LNot AvailableC30H46O4470.339609961 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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