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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:32:25 UTC
Update Date2022-03-07 02:54:11 UTC
HMDB IDHMDB0034646
Secondary Accession Numbers
  • HMDB34646
Metabolite Identification
Common Name3beta-Acetoxy-12-oxo-28,13beta-oleananolide
Description3beta-Acetoxy-12-oxo-28,13beta-oleananolide belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3beta-Acetoxy-12-oxo-28,13beta-oleananolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862597
Synonyms
ValueSource
3b-Acetoxy-12-oxo-28,13b-oleananolideGenerator
3Β-acetoxy-12-oxo-28,13β-oleananolideGenerator
4,5,9,9,13,20,20-Heptamethyl-16,23-dioxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetic acidGenerator
Chemical FormulaC32H48O5
Average Molecular Weight512.7205
Monoisotopic Molecular Weight512.350174646
IUPAC Name4,5,9,9,13,20,20-heptamethyl-16,23-dioxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate
Traditional Name4,5,9,9,13,20,20-heptamethyl-16,23-dioxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate
CAS Registry Number35959-11-6
SMILES
CC(=O)OC1CCC2(C)C(CCC3(C)C2CC(=O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C
InChI Identifier
InChI=1S/C32H48O5/c1-19(33)36-24-10-11-28(6)20(27(24,4)5)9-12-29(7)21(28)17-23(34)32-22-18-26(2,3)13-15-31(22,25(35)37-32)16-14-30(29,32)8/h20-22,24H,9-18H2,1-8H3
InChI KeyCWTOUABHZIFLIH-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point287 - 289 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.2e-05 g/LALOGPS
logP5.43ALOGPS
logP6.51ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)18.39ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity140.42 m³·mol⁻¹ChemAxon
Polarizability59.3 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+217.48931661259
DarkChem[M-H]-207.71231661259
DeepCCS[M-2H]-251.71230932474
DeepCCS[M+Na]+227.13730932474
AllCCS[M+H]+225.132859911
AllCCS[M+H-H2O]+223.832859911
AllCCS[M+NH4]+226.332859911
AllCCS[M+Na]+226.732859911
AllCCS[M-H]-218.232859911
AllCCS[M+Na-2H]-220.632859911
AllCCS[M+HCOO]-223.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3beta-Acetoxy-12-oxo-28,13beta-oleananolideCC(=O)OC1CCC2(C)C(CCC3(C)C2CC(=O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C3775.6Standard polar33892256
3beta-Acetoxy-12-oxo-28,13beta-oleananolideCC(=O)OC1CCC2(C)C(CCC3(C)C2CC(=O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C3612.5Standard non polar33892256
3beta-Acetoxy-12-oxo-28,13beta-oleananolideCC(=O)OC1CCC2(C)C(CCC3(C)C2CC(=O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C3939.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3beta-Acetoxy-12-oxo-28,13beta-oleananolide,1TMS,isomer #1CC(=O)OC1CCC2(C)C(CCC3(C)C2C=C(O[Si](C)(C)C)C24OC(=O)C5(CCC(C)(C)CC52)CCC34C)C1(C)C3693.8Semi standard non polar33892256
3beta-Acetoxy-12-oxo-28,13beta-oleananolide,1TMS,isomer #1CC(=O)OC1CCC2(C)C(CCC3(C)C2C=C(O[Si](C)(C)C)C24OC(=O)C5(CCC(C)(C)CC52)CCC34C)C1(C)C3495.3Standard non polar33892256
3beta-Acetoxy-12-oxo-28,13beta-oleananolide,1TBDMS,isomer #1CC(=O)OC1CCC2(C)C(CCC3(C)C2C=C(O[Si](C)(C)C(C)(C)C)C24OC(=O)C5(CCC(C)(C)CC52)CCC34C)C1(C)C3929.2Semi standard non polar33892256
3beta-Acetoxy-12-oxo-28,13beta-oleananolide,1TBDMS,isomer #1CC(=O)OC1CCC2(C)C(CCC3(C)C2C=C(O[Si](C)(C)C(C)(C)C)C24OC(=O)C5(CCC(C)(C)CC52)CCC34C)C1(C)C3687.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h2e-2254900000-02208c3342d01db6c4712017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 10V, Positive-QTOFsplash10-03di-0000960000-36c447fa282c3bc01ac02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 20V, Positive-QTOFsplash10-0w91-1003910000-7cca2e6172a9e2698e1d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 40V, Positive-QTOFsplash10-00lr-5216900000-60bf488e9986e5d7a79f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 10V, Negative-QTOFsplash10-03xr-1000980000-8a84c7d7ca8a78d301ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 20V, Negative-QTOFsplash10-014i-2000920000-e0a0aaa69455ca6eaa1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 40V, Negative-QTOFsplash10-056u-4000900000-eba79dc188fd8a6851002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 10V, Negative-QTOFsplash10-03di-0000090000-8d373f134d0c429be6f62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 20V, Negative-QTOFsplash10-03di-1000190000-1813619c7dff122d30ed2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 40V, Negative-QTOFsplash10-0bt9-3000490000-f770c77df29b2fc21db62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 10V, Positive-QTOFsplash10-03di-0000390000-76e184357cbd9eb567452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 20V, Positive-QTOFsplash10-03di-4134950000-e619ddb6dff13cc3aeee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-Acetoxy-12-oxo-28,13beta-oleananolide 40V, Positive-QTOFsplash10-0ika-6415960000-98952fa4b796723df66e2021-09-25Wishart 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 IDFDB013170
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76033272
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.