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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:22:14 UTC
Update Date2022-03-07 02:54:08 UTC
HMDB IDHMDB0034517
Secondary Accession Numbers
  • HMDB34517
Metabolite Identification
Common Namebeta-Glycyrrhetinic acid
Descriptionbeta-Glycyrrhetinic acid, also known as b-glycyrrhetinate or 18alpha-ga, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on beta-Glycyrrhetinic acid.
Structure
Data?1563862574
Synonyms
ValueSource
b-GlycyrrhetinateGenerator
b-Glycyrrhetinic acidGenerator
beta-GlycyrrhetinateGenerator
Β-glycyrrhetinateGenerator
Β-glycyrrhetinic acidGenerator
18alpha-GAMeSH
18beta-GAMeSH
18beta-Glycyrrhetinic acidMeSH
18 alpha-Glycyrrhetinic acidHMDB
18-Isoglycyrrhetinic acidHMDB
18a-Glycyrrhetic acidHMDB
18alpha-Olean-12-en-30-Oic acid, 3beta-hydroxy-11-oxo- (6ci,7ci,8ci)HMDB
3-Hydroxy-11-oxo-(3beta,18alpha,20beta)-olean-12-en-29-Oic acidHMDB
Isoglycyrrhetinic acidHMDB
18a-GlycyrrhetinateGenerator
18a-Glycyrrhetinic acidGenerator
18alpha-GlycyrrhetinateGenerator
18Α-glycyrrhetinateGenerator
18Α-glycyrrhetinic acidGenerator
Chemical FormulaC30H46O4
Average Molecular Weight470.6838
Monoisotopic Molecular Weight470.33960996
IUPAC Name(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-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
Traditional Name(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid
CAS Registry Number1449-05-4
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(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
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-/m1/s1
InChI KeyMPDGHEJMBKOTSU-PMTKVOBESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclohexenone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point330 - 335 °CNot Available
Boiling Point588.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.011 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.570 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.45ALOGPS
logP6.03ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.27 m³·mol⁻¹ChemAxon
Polarizability55.39 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-243.26430932474
DeepCCS[M+Na]+217.03830932474
AllCCS[M+H]+217.032859911
AllCCS[M+H-H2O]+215.432859911
AllCCS[M+NH4]+218.432859911
AllCCS[M+Na]+218.832859911
AllCCS[M-H]-213.732859911
AllCCS[M+Na-2H]-215.732859911
AllCCS[M+HCOO]-218.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-Glycyrrhetinic acid[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(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3961.7Standard polar33892256
beta-Glycyrrhetinic acid[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(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3594.0Standard non polar33892256
beta-Glycyrrhetinic acid[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(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3906.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Glycyrrhetinic acid,1TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C4029.1Semi standard non polar33892256
beta-Glycyrrhetinic acid,1TMS,isomer #2CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]3(C)CC[C@]21C3932.4Semi standard non polar33892256
beta-Glycyrrhetinic acid,1TMS,isomer #3CC1(C)[C@@H](O)CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]123879.8Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]3(C)CC[C@]21C3904.3Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TMS,isomer #2CC1(C)[C@@H](O[Si](C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]123813.1Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TMS,isomer #3CC1(C)[C@@H](O)CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]123761.9Semi standard non polar33892256
beta-Glycyrrhetinic acid,3TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]123692.0Semi standard non polar33892256
beta-Glycyrrhetinic acid,3TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]123688.4Standard non polar33892256
beta-Glycyrrhetinic acid,1TBDMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C4217.5Semi standard non polar33892256
beta-Glycyrrhetinic acid,1TBDMS,isomer #2CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)CC[C@]21C4167.9Semi standard non polar33892256
beta-Glycyrrhetinic acid,1TBDMS,isomer #3CC1(C)[C@@H](O)CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]124113.6Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TBDMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@H]3C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)CC[C@]21C4344.4Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TBDMS,isomer #2CC1(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]124233.6Semi standard non polar33892256
beta-Glycyrrhetinic acid,2TBDMS,isomer #3CC1(C)[C@@H](O)CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]124202.2Semi standard non polar33892256
beta-Glycyrrhetinic acid,3TBDMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]124291.1Semi standard non polar33892256
beta-Glycyrrhetinic acid,3TBDMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]124381.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Glycyrrhetinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0216900000-74f3465dcca9019ca9512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Glycyrrhetinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1021592000-56e1df4c4a6a4d9460dd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Glycyrrhetinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid Linear Ion Trap , negative-QTOFsplash10-004i-0000900000-3483213eb90b7762fb722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid Linear Ion Trap , negative-QTOFsplash10-004i-0000900000-5fa2c06264507f4f3c152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid Linear Ion Trap , positive-QTOFsplash10-004i-0342900000-10ea26e7f92faaef6f2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid 40V, Positive-QTOFsplash10-05i0-0920100000-2d3223a633769dc0e6382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid 20V, Positive-QTOFsplash10-00di-0000900000-9e7d44415d3a88016d9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Glycyrrhetinic acid 10V, Positive-QTOFsplash10-00di-0000900000-b9d584487d89a81e7f292021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 10V, Positive-QTOFsplash10-0uk9-0000900000-4fd1d9106fe4e18c8fa42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 20V, Positive-QTOFsplash10-0pbi-0101900000-219872d2c000651a313b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 40V, Positive-QTOFsplash10-0ar0-2908700000-29dd3e801a0b370c5cf82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 10V, Negative-QTOFsplash10-014i-0000900000-f48f58fd0b19d7113d852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 20V, Negative-QTOFsplash10-0690-0000900000-dd269ff3ff161d041bad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 40V, Negative-QTOFsplash10-0pb9-1001900000-473216311a73be4966f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 10V, Negative-QTOFsplash10-014i-0000900000-d60788820b8857f5a5d52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 20V, Negative-QTOFsplash10-014i-0000900000-d60788820b8857f5a5d52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 40V, Negative-QTOFsplash10-01bc-2000900000-2ccd14915fa2a3e27d8f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 10V, Positive-QTOFsplash10-00di-0000900000-296f14837562a59678ca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 20V, Positive-QTOFsplash10-05i0-0001900000-0227108f5ac33bae6da32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Glycyrrhetinic acid 40V, Positive-QTOFsplash10-01b9-4329000000-15bb26ca9bcb86b1f04e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013018
KNApSAcK IDC00003521
Chemspider ID66115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73398
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1700431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.