Glycyrrhetinate (BioCAD00000011786)
Metabolite Card
Formula: C30H46O4 (470.3396)
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
Synonyms [en]
enoxolone; Glycyrrhetinic Acid; Glycyrrhetinate; Glycyrrhetic acid; 18b-Glycyrrhetinic acid; Uralenic acid
Reviewed
Last reviewed on 2024-06-28.
Cite this Page
Glycyrrhetinate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000011786). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was first obtained from the herb liquorice. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties (PMID:32106571). In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH2)CO2K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity.
Entity Information
DBLinks
- CAS Registry Number: 1449-05-4
- PubChem CID: 18526330
- ChEBI: 17573
- HMDB: HMDB0011628
- LipidMaps: LMPR0106150014
- KEGG: C02283
- BioCyc:
- NCBI MeSH: Glycyrrhetinic Acid
- Wikipedia: Enoxolone
Other DBLinks
- CAS Registry Number: 105870-59-5
- CAS Registry Number: 107420-91-7
- CAS Registry Number: 1449-05-4
- CAS Registry Number: 1449-05-4 471-53-4
- CAS Registry Number: 15301-63-0
- CAS Registry Number: 471-53-4
- CAS Registry Number: NA
- PubChem: 10114
- PubChem: 11870423
- PubChem: 133568304
- PubChem: 170924268
- PubChem: 17751012
- PubChem: 18526330
- PubChem: 3230
- PubChem: 5340
- PubChem: 5702287
- PubChem: 68265830
- PubChem: 9897771
- ChEBI: ChEBI:17573
- ChEBI: ChEBI:30853
- HMDB: HMDB0011628
- HMDB: HMDB11628
- LipidMaps: LMPR0106150014
- KEGG: C02283
- NCBI MeSH: 18alpha-glycyrrhetinic acid
- NCBI MeSH: Glycyrrhetinic Acid
- Wikipedia: Enoxolone
- Wikipedia: Glycyrrhetinic_acid
- DrugBank: DB13089
- RefMet: RM0043795
- MoNA: BML00475
- MoNA: BML00484
- MoNA: BML00501
- MoNA: BML00509
- MoNA: BML00517
- MoNA: BML81160
- MoNA: BML81161
- MoNA: BML81162
- MoNA: BML81163
- MoNA: CCMSLIB00000579309
- MoNA: EQ326301
- MoNA: EQ326302
- MoNA: EQ326303
- MoNA: EQ326304
- MoNA: EQ326305
- MoNA: EQ326306
- MoNA: EQ326307
- MoNA: EQ326308
- MoNA: EQ326309
- MoNA: EQ326351
- MoNA: EQ326352
- MoNA: EQ326353
- MoNA: EQ326354
- MoNA: EQ326355
- MoNA: EQ326356
- MoNA: EQ326357
- MoNA: EQ326358
- MoNA: EQ326359
- MoNA: HMDB0011628_ms_ms_1218240
- MoNA: HMDB0011628_ms_ms_1218241
- MoNA: HMDB0011628_ms_ms_1218242
- MoNA: HMDB0011628_ms_ms_1218243
- MoNA: HMDB0011628_ms_ms_1218244
- MoNA: HMDB0011628_ms_ms_1218245
- MoNA: HMDB0011628_ms_ms_1218246
- MoNA: HMDB0011628_ms_ms_1218255
- MoNA: HMDB0011628_ms_ms_1218256
- MoNA: HMDB0011628_ms_ms_1218257
- MoNA: HMDB0011628_ms_ms_1218258
- MoNA: HMDB0011628_ms_ms_1218259
- MoNA: HMDB0011628_ms_ms_1218260
- MoNA: HMDB0011628_ms_ms_1218261
- MoNA: HMDB0011628_ms_ms_1218262
- MoNA: HMDB0011628_ms_ms_1218263
- MoNA: HMDB0011628_ms_ms_1218264
- MoNA: HMDB0011628_ms_ms_1218265
- MoNA: HMDB0011628_ms_ms_1218266
- MoNA: HMDB0011628_ms_ms_1218267
- MoNA: HMDB0011628_ms_ms_1218268
- MoNA: HMDB0011628_ms_ms_1218269
- MoNA: HMDB0011628_ms_ms_1218270
- MoNA: HMDB0011628_ms_ms_1218271
- MoNA: HMDB0011628_ms_ms_1218272
- MoNA: HMDB0011628_ms_ms_1218273
- MoNA: HMDB0011628_ms_ms_1218274
- MoNA: HMDB0011628_ms_ms_1218275
- MoNA: HMDB0011628_ms_ms_1218276
- MoNA: HMDB0011628_ms_ms_1218277
- MoNA: HMDB0011628_ms_ms_1218278
- MoNA: HMDB0011628_ms_ms_1218279
- MoNA: HMDB0011628_ms_ms_1218280
- MoNA: HMDB0011628_ms_ms_1218281
- MoNA: HMDB0011628_ms_ms_1218282
- MoNA: HMDB0011628_ms_ms_1218283
- MoNA: HMDB0011628_ms_ms_1218284
- MoNA: HMDB0011628_ms_ms_1218285
- MoNA: HMDB0011628_ms_ms_1218286
- MoNA: HMDB0011628_ms_ms_1218287
- MoNA: HMDB0011628_ms_ms_1218288
- MoNA: HMDB0011628_ms_ms_1218289
- MoNA: HMDB0011628_ms_ms_1218290
- MoNA: HMDB0011628_ms_ms_1218291
- MoNA: HMDB0011628_ms_ms_1218292
- MoNA: HMDB0011628_ms_ms_1218293
- MoNA: HMDB0011628_ms_ms_1218294
- MoNA: HMDB0011628_ms_ms_1218295
- MoNA: HMDB0011628_ms_ms_1218296
- MoNA: HMDB0011628_ms_ms_1218297
- MoNA: HMDB0011628_ms_ms_1218298
- MoNA: HMDB0011628_ms_ms_1218299
- MoNA: HMDB0011628_ms_ms_1218300
- MoNA: HMDB0011628_ms_ms_1218301
- MoNA: HMDB0011628_ms_ms_1218302
- MoNA: HMDB0011628_ms_ms_1218303
- MoNA: HMDB0011628_ms_ms_1218304
- MoNA: HMDB0011628_ms_ms_1218305
- MoNA: HMDB0011628_ms_ms_1218306
- MoNA: HMDB0011628_ms_ms_1218307
- MoNA: HMDB0011628_ms_ms_1218308
- MoNA: HMDB0011628_ms_ms_1218309
- MoNA: HMDB0011628_ms_ms_1218310
- MoNA: HMDB0011628_ms_ms_1218311
- MoNA: KO000933
- MoNA: KO000934
- MoNA: KO000935
- MoNA: KO000936
- MoNA: KO000937
- MoNA: KO003034
- MoNA: KO003035
- MoNA: KO003036
- MoNA: KO003037
- MoNA: KO003038
- MoNA: KO008978
- MoNA: KO008979
- MoNA: KO008980
- MoNA: KO008981
- MoNA: KO008982
- MoNA: KO008983
- MoNA: KO008984
- MoNA: KO008985
- MoNA: MetaboBASE0175
- MoNA: MetaboBASE0176
- MoNA: MetaboBASE0177
- MoNA: MetaboBASE0178
- MoNA: MetaboBASE0179
- MoNA: MetaboBASE0180
- MoNA: MetaboBASE0181
- MoNA: MoNA003259
- MoNA: VF-NPL-LTQ000071
- MoNA: VF-NPL-LTQ000072
- MoNA: VF-NPL-LTQ000073
- MoNA: VF-NPL-LTQ000074
- MoNA: VF-NPL-LTQ000273
- MoNA: VF-NPL-LTQ000274
- MoNA: VF-NPL-LTQ000275
- MoNA: VF-NPL-LTQ000276
- MoNA: VF-NPL-LTQ006937
- MoNA: VF-NPL-LTQ006938
- MoNA: VF-NPL-LTQ006939
- MoNA: VF-NPL-LTQ006940
- MoNA: VF-NPL-QEHF000187
- MoNA: VF-NPL-QEHF000188
- MoNA: VF-NPL-QEHF000189
- MoNA: VF-NPL-QEHF000190
- MoNA: VF-NPL-QEHF000191
- MoNA: VF-NPL-QEHF000192
- MoNA: VF-NPL-QEHF000193
- MoNA: VF-NPL-QEHF000194
- MoNA: VF-NPL-QEHF000195
- MoNA: VF-NPL-QEHF000196
- MoNA: VF-NPL-QEHF000197
- MoNA: VF-NPL-QEHF000198
- MoNA: VF-NPL-QEHF000571
- MoNA: VF-NPL-QEHF000572
- MoNA: VF-NPL-QEHF000573
- MoNA: VF-NPL-QEHF000574
- MoNA: VF-NPL-QEHF000575
- MoNA: VF-NPL-QEHF000576
- MoNA: VF-NPL-QEHF013507
- MoNA: VF-NPL-QEHF013508
- MoNA: VF-NPL-QEHF013509
- MoNA: VF-NPL-QEHF013510
- MoNA: VF-NPL-QEHF013511
- MoNA: VF-NPL-QEHF013512
- MoNA: VF-NPL-QTOF002472
- MoNA: VF-NPL-QTOF002473
- MoNA: VF-NPL-QTOF002474
- MoNA: VF-NPL-QTOF002475
- MoNA: VF-NPL-QTOF002476
- MoNA: VF-NPL-QTOF002477
- MoNA: VF-NPL-QTOF002478
- MoNA: VF-NPL-QTOF002479
- MoNA: VF-NPL-QTOF002480
- MoNA: VF-NPL-QTOF007559
- MoNA: VF-NPL-QTOF007560
- MoNA: VF-NPL-QTOF007561
- MoNA: VF-NPL-QTOF007562
- MoNA: VF-NPL-QTOF007563
- MoNA: VF-NPL-QTOF007564
- MoNA: VF-NPL-QTOF007565
- MoNA: VF-NPL-QTOF007566
- MoNA: VF-NPL-QTOF007567
- MoNA: WA001651
- MoNA: WA001652
- MoNA: WA001653
- MoNA: WA001654
- MoNA: WA001655
- Metlin: METLIN_43857
- Metlin: METLIN_53782
- Coconut NaturalProduct: CNP0078193.1
- Coconut NaturalProduct: CNP0078195.1
- Coconut NaturalProduct: CNP0130164.1
- Coconut NaturalProduct: CNP0159281.1
- Coconut NaturalProduct: CNP0167821.1
- Coconut NaturalProduct: CNP0264563.15
- Coconut NaturalProduct: CNP0264563.2
- Coconut NaturalProduct: CNP0264563.21
- Coconut NaturalProduct: CNP0264563.26
- Coconut NaturalProduct: CNP0264563.6
- Coconut NaturalProduct: CNP0264563.8
Class / Ontology
- WishartLab ClassyFire: [Triterpenoids] Triterpenoids
- RefMet: [C30 isoprenoids] C30 isoprenoids
- LipidMaps: [C30 isoprenoids (triterpenes) [PR0106]] C30 isoprenoids (triterpenes) [PR0106]
- ChEBI: [CHEBI:30853] glycyrrhetinic acid
- Coconut NaturalProduct: [Oleanane triterpenoids] Oleanane triterpenoids
- Coconut NaturalProduct: [Ursane and Taraxastane triterpenoids] Ursane and Taraxastane triterpenoids
- Coconut NaturalProduct: [Multiflorane triterpenoids] Multiflorane triterpenoids
Metabolic Network
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03906 | 3.2.1.128 | glycyrrhizinate glucuronosylhydrolase |
| KEGG:R10315 | 1.14.14.115 | glycyrrhetaldehyde,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (30-hydroxylating) |
| KEGG:R10316 | 1.14.14.115 | 11-oxo-beta-amyrin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (30-hydroxylating) |
| Rhea:RHEA:17370 | 3.2.1.128 | glycyrrhizin + H2O => 2-(β-D-glucuronosyl)-D-glucuronate + glycyrrhetinate |
| Rhea:RHEA:17371 | 3.2.1.128 | 2-(β-D-glucuronosyl)-D-glucuronate + glycyrrhetinate => glycyrrhizin + H2O |
| Rhea:RHEA:17372 | 3.2.1.128 | glycyrrhizin + H2O <=> 2-(β-D-glucuronosyl)-D-glucuronate + glycyrrhetinate |
| Rhea:RHEA:35500 | 1.14.14.115 | 11-oxo-β-amyrin + 3 reduced [NADPH—hemoprotein reductase] + 3 O2 => glycyrrhetinate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+ |
| Rhea:RHEA:35501 | 1.14.14.115 | glycyrrhetinate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+ => 11-oxo-β-amyrin + 3 reduced [NADPH—hemoprotein reductase] + 3 O2 |
| Rhea:RHEA:35502 | 1.14.14.115 | 11-oxo-β-amyrin + 3 reduced [NADPH—hemoprotein reductase] + 3 O2 <=> glycyrrhetinate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+ |
| Rhea:RHEA:35512 | glycyrrhetaldehyde + reduced [NADPH—hemoprotein reductase] + O2 => glycyrrhetinate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ | |
| Rhea:RHEA:35513 | glycyrrhetinate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ => glycyrrhetaldehyde + reduced [NADPH—hemoprotein reductase] + O2 | |
| Rhea:RHEA:35514 | glycyrrhetaldehyde + reduced [NADPH—hemoprotein reductase] + O2 <=> glycyrrhetinate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ |
Mass Spectrum
Organism Source
Taxonomy Source
- Dillenia papuana [ncbi taxid: 1085409]
- Dillenia papuana [ncbi taxid: 1085409]
- Eucalyptus camaldulensis var. obtusa [ncbi taxid: ]
- Dillenia papuana [ncbi taxid: 1085409]
- Sandoricum indicum [ncbi taxid: 2077122]
- Glycyrrhiza aspera [ncbi taxid: 74709]
- Glycyrrhiza glabra [ncbi taxid: 49827]
- Glycyrrhiza inflata [ncbi taxid: 74614]
- Glycyrrhiza kansuensis [ncbi taxid: ]
- Glycyrrhiza uralensis [ncbi taxid: 74613]
- Glycyrrhiza yunnanensis [ncbi taxid: 912971]
- Homo sapiens [ncbi taxid: 9606]
- Iris division [ncbi taxid: ]
- Lentinus tigrinus [ncbi taxid: 5365]
- Mitracarpus scaber [ncbi taxid: ]
- Radix glycyrrhizae praeparata [ncbi taxid: ]
- Radix glycyrrhizae preparata [ncbi taxid: ]
- Radix glycyrrhizae uralensis [ncbi taxid: ]
- Schlegelella brevitalea DSM 7029 [n.a.] [ncbi taxid: ]
- Viburnum hupehense [ncbi taxid: 1127649]
- Walsura robusta [ncbi taxid: 1489958]
- Abrus pulchellus [ncbi taxid: 192852]
- Glycyrrhiza glabra [ncbi taxid: 49827]
- Glycyrrhiza inflata [ncbi taxid: 74614]
- Glycyrrhiza uralensis [ncbi taxid: 74613]
- Prunella vulgaris [ncbi taxid: 39358]
- Radix glycyrrhizae praeparata [ncbi taxid: ]
- Radix glycyrrhizae preparata [ncbi taxid: ]
- Radix glycyrrhizae uralensis [ncbi taxid: ]
- Echinopora lamellosa [ncbi taxid: 46694]
- Glycyrrhiza glabra [ncbi taxid: 49827]
- Glycyrrhiza inflata [ncbi taxid: 74614]
- Glycyrrhiza uralensis [ncbi taxid: 74613]
Pathway Synthetic
| pathway id | name |
|---|---|
| PlantCyc:SOY_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:PIGEONPEA_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:LJAPONICUS_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:MTRUNCATULA_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:APPLERINGACACIA_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:REDCLOVER_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:COMMONBEAN_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:STORA_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:PLANT_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:CARIETINUM_ICC4958_PWY-7066 | glycyrrhetinate biosynthesis |
| PlantCyc:BAMBARABEAN_PWY-7066 | glycyrrhetinate biosynthesis |