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 Online Resources

Record IDSourceDescriptionView
BML00475MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00484MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00501MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00509MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00517MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81160MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81161MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
KO000933MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000934MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000935MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000936MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000937MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KO003034MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO003035MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO003036MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO003037MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO003038MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KO008978MassBankLC-ESI-IT Spectrum - 0.90, unspecifiedView Spectra
KO008979MassBankLC-ESI-IT Spectrum - 0.90/0.80, unspecifiedView Spectra
KO008980MassBankLC-ESI-IT Spectrum - 0.90/0.80, unspecifiedView Spectra
KO008981MassBankLC-ESI-IT Spectrum - 0.90/0.85, unspecifiedView Spectra
KO008982MassBankLC-ESI-IT Spectrum - 0.90/0.65, unspecifiedView Spectra
KO008983MassBankLC-ESI-IT Spectrum - 0.90/0.60, unspecifiedView Spectra
KO008984MassBankLC-ESI-IT Spectrum - 0.70/0.60, unspecifiedView Spectra
KO008985MassBankLC-ESI-IT Spectrum - 0.80/0.50, unspecifiedView Spectra
WA001651MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA001652MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA001653MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA001654MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA001655MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra

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
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