precursor metabolite

Showing entry for Glycyrrhizin

Identification

PhytoHub ID
PHUB000171
Name
Glycyrrhizin
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
822.942
Monoisotopic Mass
822.403785916
Chemical Formula
C42H62O16
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
InChI Key
LPLVUJXQOOQHMX-QWBHMCJMSA-N
InChI Identifier
InChI=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
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
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
5.45e-02 g/l
LogS (ALOGPS)
-4.18
LogP (ALOGPS)
2.78
Hydrogen Acceptors
16
Hydrogen Donors
8
Rotatable Bond Count
7
Polar Surface Area
267.03999999999996
Refractivity
198.8299000000001
Polarizability
86.29598239399198
Formal Charge
0
Physiological Charge
-3
pKa (strongest basic)
-3.7319808463593795
pKa (strongest acidic)
2.961005004154196
Number of Rings
7
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

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

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Terpene glycosides
Direct Parent Name
Triterpene saponins
Alternative Parent Names
["Acetals", "Beta hydroxy acids and derivatives", "Carboxylic acids", "Cyclohexenones", "Disaccharides", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Polyols", "Pyrans", "Secondary alcohols", "Tricarboxylic acids and derivatives", "Triterpenoids"]
External Descriptor Annotations
["enone", "glucosiduronic acid", "pentacyclic triterpenoid", "tricarboxylic acid", "triterpenoid saponin"]
Substituent Names
["1-o-glucuronide", "Acetal", "Alcohol", "Aliphatic heteropolycyclic compound", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cyclohexenone", "Disaccharide", "Glucuronic acid or derivatives", "Glycosyl compound", "Hydrocarbon derivative", "Hydroxy acid", "Ketone", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Polyol", "Pyran", "Secondary alcohol", "Tricarboxylic acid or derivatives", "Triterpene saponin", "Triterpenoid"]

Spectra from Phytohub

Spectrum TypeInstrument TypeTechnologyIon ModeCollision EnergyView
Predicted GC-MSGC-MSPredicted by CFM-ID 2.0, energy0EiNot AvailableView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemsnegativeVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemsnegativeVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemsnegativeVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemsnegativeVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemsnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-TOFinstrument=impact HDnegativeVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemspositiveVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemspositiveVView Spectrum
LC-MS/MSLC-ESI-QQinstrument=API3000, Applied BiosystemspositiveVView 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

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Glycyrrhizin Glycyrrhetinic acidhuman ratbile, plasma, urinegut microbiota metabolite12h-24h<20 nmol/LNot AvailableC30H46O4470.339609961 Detailed Intervention Studies Publications
Glycyrrhizin Glycyrrhizinhumanplasmaunchanged3h-5h<20 nmol/LNot AvailableC42H62O16822.403785916 Detailed Intervention Studies Publications
Glycyrrhizin Glycyrrhetinic acid 3-O-glucuronidehuman ratbile, plasma, urineunknownNot AvailableNot AvailableNot AvailableC36H54O10646.371697939 Publications
Glycyrrhizin Glycyrrhetinic acid 30-O-glucuronideratbileunknownNot AvailableNot AvailableNot AvailableC36H54O10646.371697939 Publications
Glycyrrhizin Glycyrrhetinic acid 3-O-sulfatehuman ratbile, plasma, urineunknownNot AvailableNot AvailableNot AvailableC30H46O7S550.296424995 Publications
Glycyrrhizin Glycyrrhetinic acid 3-O-sulfate-30-glucuronideratbileunknownNot AvailableNot AvailableNot AvailableC36H54O13S726.328512973 Publications
Glycyrrhizin 3 β-monoglucuronyl-18-β-glycyrrhetinic acidhumanurinehost metabolismNot AvailableNot Available<1%C36H54O10646.371697939 Detailed Intervention Studies Publications
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