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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:14 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033728
Secondary Accession Numbers
  • HMDB33728
Metabolite Identification
Common NamePubesenolide
DescriptionGlycyrrhetol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Glycyrrhetol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862451
Synonyms
ValueSource
3,30-Dihydroxy-12-oleanen-11-oneHMDB
SominoneHMDB
Chemical FormulaC28H42O5
Average Molecular Weight458.6301
Monoisotopic Molecular Weight458.303224454
IUPAC Name6-(1-{3,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-{3,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
CAS Registry Number98569-64-3
SMILES
CC(C1CCC2C3CC=C4CC(O)CC(O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1
InChI Identifier
InChI=1S/C28H42O5/c1-15-11-24(33-26(32)20(15)14-29)16(2)21-7-8-22-19-6-5-17-12-18(30)13-25(31)28(17,4)23(19)9-10-27(21,22)3/h5,16,18-19,21-25,29-31H,6-14H2,1-4H3
InChI KeyFYYIHVSEGVWNCF-UHFFFAOYSA-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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP3.09ALOGPS
logP3.15ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.31ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity128.81 m³·mol⁻¹ChemAxon
Polarizability53.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.52931661259
DarkChem[M-H]-200.32731661259
DeepCCS[M-2H]-242.88530932474
DeepCCS[M+Na]+218.11430932474
AllCCS[M+H]+215.032859911
AllCCS[M+H-H2O]+213.132859911
AllCCS[M+NH4]+216.832859911
AllCCS[M+Na]+217.332859911
AllCCS[M-H]-211.332859911
AllCCS[M+Na-2H]-213.332859911
AllCCS[M+HCOO]-215.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PubesenolideCC(C1CCC2C3CC=C4CC(O)CC(O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O13230.7Standard polar33892256
PubesenolideCC(C1CCC2C3CC=C4CC(O)CC(O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O13453.4Standard non polar33892256
PubesenolideCC(C1CCC2C3CC=C4CC(O)CC(O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O14198.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pubesenolide,1TMS,isomer #1CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C)CC(O)C5(C)C4CCC23C)C13995.6Semi standard non polar33892256
Pubesenolide,1TMS,isomer #2CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O[Si](C)(C)C)C5(C)C4CCC23C)C13999.0Semi standard non polar33892256
Pubesenolide,1TMS,isomer #3CC1=C(CO[Si](C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O)C5(C)C4CCC23C)C14001.0Semi standard non polar33892256
Pubesenolide,2TMS,isomer #1CC1=C(CO[Si](C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C)CC(O)C5(C)C4CCC23C)C14005.1Semi standard non polar33892256
Pubesenolide,2TMS,isomer #2CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C5(C)C4CCC23C)C14016.1Semi standard non polar33892256
Pubesenolide,2TMS,isomer #3CC1=C(CO[Si](C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O[Si](C)(C)C)C5(C)C4CCC23C)C13997.5Semi standard non polar33892256
Pubesenolide,3TMS,isomer #1CC1=C(CO[Si](C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C5(C)C4CCC23C)C13942.6Semi standard non polar33892256
Pubesenolide,1TBDMS,isomer #1CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CC(O)C5(C)C4CCC23C)C14223.3Semi standard non polar33892256
Pubesenolide,1TBDMS,isomer #2CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O[Si](C)(C)C(C)(C)C)C5(C)C4CCC23C)C14220.2Semi standard non polar33892256
Pubesenolide,1TBDMS,isomer #3CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O)C5(C)C4CCC23C)C14240.2Semi standard non polar33892256
Pubesenolide,2TBDMS,isomer #1CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CC(O)C5(C)C4CCC23C)C14431.3Semi standard non polar33892256
Pubesenolide,2TBDMS,isomer #2CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C5(C)C4CCC23C)C14422.5Semi standard non polar33892256
Pubesenolide,2TBDMS,isomer #3CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O)CC(O[Si](C)(C)C(C)(C)C)C5(C)C4CCC23C)C14411.6Semi standard non polar33892256
Pubesenolide,3TBDMS,isomer #1CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C(C)C2CCC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C5(C)C4CCC23C)C14539.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pubesenolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0012900000-736e1f9ea5a8ab4325bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pubesenolide GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-1010569000-f64749fa22bd94805e392017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pubesenolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pubesenolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 10V, Positive-QTOFsplash10-006x-0002900000-cd71ec43a280bf5350de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 20V, Positive-QTOFsplash10-00dl-1018900000-f696ccbadda7d5f194102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 40V, Positive-QTOFsplash10-00fs-0039200000-c629b142ceda048cf2e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 10V, Negative-QTOFsplash10-0a4i-0001900000-47359324af54113d86322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 20V, Negative-QTOFsplash10-0a70-0001900000-635384d7dc62f3e719ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 40V, Negative-QTOFsplash10-001l-9107200000-8485ad78502f7837cf622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 10V, Positive-QTOFsplash10-0aor-0023900000-208e203966629860c5ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 20V, Positive-QTOFsplash10-0603-0498600000-443c3bf81d9735838fc62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 40V, Positive-QTOFsplash10-03di-0961400000-4453196745b6a053a20b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 10V, Negative-QTOFsplash10-0a4i-0000900000-eca9035f990f3541da9b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 20V, Negative-QTOFsplash10-0a4i-0001900000-b0a1b4a36201e534e7a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pubesenolide 40V, Negative-QTOFsplash10-0a4j-9505800000-2b68c5521266404ff5e92021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB019319
KNApSAcK IDNot Available
Chemspider ID4476515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317761
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.