Glycyrrhizin
precursor
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[[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
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 |