PhytoHub: Showing entry for Glycyrrhizin

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[[email protected]](O[[email protected]]4O[C@@H]([C@@H](O)[[email protected]](O)[[email protected]]4O[C@@H]4O[C@@H]([C@@H](O)[[email protected]](O)[[email protected]]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

External Links

ChEBI: 15939
PubChem: 14982
Chemistry Dashboard: DTXSID8047006
MetaboLights: MTBLC15939
PeakForestCompound: 000158

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 Phytochemical	Family	Class	Sub-class
Glycyrrhizin	Terpenoids	Triterpenoids	Saponins	Show 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 Online Resources

Record ID	Source	Description	View
KO000898	MassBank	LC-ESI-QQ Spectrum - 10 V, unspecified	View Spectra
KO000899	MassBank	LC-ESI-QQ Spectrum - 20 V, unspecified	View Spectra
KO000900	MassBank	LC-ESI-QQ Spectrum - 30 V, unspecified	View Spectra
KO000901	MassBank	LC-ESI-QQ Spectrum - 40 V, unspecified	View Spectra
KO000902	MassBank	LC-ESI-QQ Spectrum - 50 V, unspecified	View Spectra
KO002999	MassBank	LC-ESI-QQ Spectrum - 10 V, unspecified	View Spectra
KO003000	MassBank	LC-ESI-QQ Spectrum - 20 V, unspecified	View Spectra
KO003001	MassBank	LC-ESI-QQ Spectrum - 30 V, unspecified	View Spectra
KO003002	MassBank	LC-ESI-QQ Spectrum - 40 V, unspecified	View Spectra
KO003003	MassBank	LC-ESI-QQ Spectrum - 50 V, unspecified	View Spectra
PR100137	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100258	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100559	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100560	MassBank	LC-ESI-QTOF Spectrum - 30 V, unspecified	View Spectra
PR100681	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100682	MassBank	LC-ESI-QTOF Spectrum - 30 V, unspecified	View Spectra
PS023801	ReSpect	N/A Spectrum - 10, [M+H]+	View Spectra
PS023802	ReSpect	N/A Spectrum - 20, [M+H]+	View Spectra
PS023803	ReSpect	N/A Spectrum - 30, [M+H]+	View Spectra
PS023804	ReSpect	N/A Spectrum - 40, [M+H]+	View Spectra
PS023805	ReSpect	N/A Spectrum - 50, [M+H]+	View Spectra
PS023806	ReSpect	N/A Spectrum - 60, [M+H]+	View Spectra
PS023807	ReSpect	N/A Spectrum - 10, [M-H]-	View Spectra
PS023808	ReSpect	N/A Spectrum - 20, [M-H]-	View Spectra
PS023809	ReSpect	N/A Spectrum - 30, [M-H]-	View Spectra
PS023810	ReSpect	N/A Spectrum - 40, [M-H]-	View Spectra
PS023811	ReSpect	N/A Spectrum - 50, [M-H]-	View Spectra
PS023812	ReSpect	N/A Spectrum - 60, [M-H]-	View Spectra
PS044001	ReSpect	N/A Spectrum - 10, [M+H]+	View Spectra
PS044002	ReSpect	N/A Spectrum - 20, [M+H]+	View Spectra
PS044003	ReSpect	N/A Spectrum - 30, [M+H]+	View Spectra
PS044004	ReSpect	N/A Spectrum - 40, [M+H]+	View Spectra
PS044005	ReSpect	N/A Spectrum - 50, [M+H]+	View Spectra
PS044006	ReSpect	N/A Spectrum - 60, [M+H]+	View Spectra
PS044007	ReSpect	N/A Spectrum - 10, [M-H]-	View Spectra
PS044008	ReSpect	N/A Spectrum - 20, [M-H]-	View Spectra
PS044009	ReSpect	N/A Spectrum - 30, [M-H]-	View Spectra
PS044010	ReSpect	N/A Spectrum - 40, [M-H]-	View Spectra
PS044011	ReSpect	N/A Spectrum - 50, [M-H]-	View Spectra
PS044012	ReSpect	N/A Spectrum - 60, [M-H]-	View Spectra
TY000021	MassBank	LC-ESI-ITTOF Spectrum - -, [M-H]-	View Spectra

Food Sources

	Name	Group
	Liquorice	Confectioneries and desserts	Publications	Show

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Glycyrrhizin	Liquorice	Confectioneries and desserts	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Glycyrrhizin	Glycyrrhetinic acid	human rat	bile, plasma, urine	gut microbiota metabolite	12h-24h	<20 nmol/L	Not Available	C₃₀H₄₆O₄	470.339609961	Detailed Intervention Studies	Publications
Glycyrrhizin	Glycyrrhizin	human	plasma	unchanged	3h-5h	<20 nmol/L	Not Available	C₄₂H₆₂O₁₆	822.403785916	Detailed Intervention Studies	Publications
Glycyrrhizin	Glycyrrhetinic acid 3-O-glucuronide	human rat	bile, plasma, urine	unknown	Not Available	Not Available	Not Available	C₃₆H₅₄O₁₀	646.371697939		Publications
Glycyrrhizin	Glycyrrhetinic acid 30-O-glucuronide	rat	bile	unknown	Not Available	Not Available	Not Available	C₃₆H₅₄O₁₀	646.371697939		Publications
Glycyrrhizin	Glycyrrhetinic acid 3-O-sulfate	human rat	bile, plasma, urine	unknown	Not Available	Not Available	Not Available	C₃₀H₄₆O₇S	550.296424995		Publications
Glycyrrhizin	Glycyrrhetinic acid 3-O-sulfate-30-glucuronide	rat	bile	unknown	Not Available	Not Available	Not Available	C₃₆H₅₄O₁₃S	726.328512973		Publications
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	human	urine	host metabolism	Not Available	Not Available	<1%	C₃₆H₅₄O₁₀	646.371697939	Detailed Intervention Studies	Publications

Inter-Individual Variations Metabolism

Food Phytochemical	Metabolite	Effect	Value
Glycyrrhizin	Glycyrrhetinic acid	BMI	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Smoking	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Ethnicity	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Genotype	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Microbiota	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Sex	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Age	Not studied
Glycyrrhizin	Glycyrrhetinic acid	Health-Status	Not studied
Glycyrrhizin	Glycyrrhizin	BMI	Not studied
Glycyrrhizin	Glycyrrhizin	Smoking	Not studied
Glycyrrhizin	Glycyrrhizin	Ethnicity	Not studied
Glycyrrhizin	Glycyrrhizin	Genotype	Not studied
Glycyrrhizin	Glycyrrhizin	Microbiota	Not studied
Glycyrrhizin	Glycyrrhizin	Sex	Not studied
Glycyrrhizin	Glycyrrhizin	Age	Not studied
Glycyrrhizin	Glycyrrhizin	Health-Status	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	BMI	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Smoking	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Ethnicity	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Genotype	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Microbiota	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Sex	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Age	Not studied
Glycyrrhizin	3 β-monoglucuronyl-18-β-glycyrrhetinic acid	Health-Status	Not studied
Glycyrrhizin	Glycyrrhizin	BMI	Not studied
Glycyrrhizin	Glycyrrhizin	Smoking	Not studied
Glycyrrhizin	Glycyrrhizin	Ethnicity	Not studied
Glycyrrhizin	Glycyrrhizin	Genotype	Not studied
Glycyrrhizin	Glycyrrhizin	Microbiota	Not studied
Glycyrrhizin	Glycyrrhizin	Sex	Not studied
Glycyrrhizin	Glycyrrhizin	Age	Not studied
Glycyrrhizin	Glycyrrhizin	Health-Status	Not studied

Back

Showing entry for Glycyrrhizin

Identification

Structure for Glycyrrhizin

Calculated Properties

External Links

Taxonomy as Food Phytochemical

Taxonomy as Metabolite

Taxonomy of its Food Phytochemical Precursor(s)

Classyfire Taxonomy

Spectra from Online Resources

Food Sources

Food Sources of its Food Phytochemical(s)

Role as Biomarker of intake

Metabolism

Inter-Individual Variations Metabolism