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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:33:10 UTC
Update Date2022-03-07 02:54:11 UTC
HMDB IDHMDB0034655
Secondary Accession Numbers
  • HMDB34655
Metabolite Identification
Common Name3-Epikatonic acid
Description3-Epikatonic acid, also known as 3-epikatonate, 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 3-Epikatonic acid.
Structure
Data?1563862598
Synonyms
ValueSource
3-EpikatonateGenerator
3-Hydroxy-(3beta,20alpha)-olean-12-en-29-Oic acidHMDB
Epikatonic acidHMDB
Chemical FormulaC30H48O3
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
IUPAC Name(2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-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(2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic acid
CAS Registry Number76035-62-6
SMILES
[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[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/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,26+,27+,28-,29+,30+/m0/s1
InChI KeyJZFSMVXQUWRSIW-FWXFQHTDSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • 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 Point283 - 284 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00055 g/LALOGPS
logP7.19ALOGPS
logP6.59ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.62 m³·mol⁻¹ChemAxon
Polarizability54.66 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
DarkChem[M+H]+206.78231661259
DarkChem[M-H]-199.23231661259
DeepCCS[M-2H]-242.09130932474
DeepCCS[M+Na]+216.03730932474
AllCCS[M+H]+218.232859911
AllCCS[M+H-H2O]+216.632859911
AllCCS[M+NH4]+219.732859911
AllCCS[M+Na]+220.132859911
AllCCS[M-H]-212.032859911
AllCCS[M+Na-2H]-214.032859911
AllCCS[M+HCOO]-216.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Epikatonic acid[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3259.8Standard polar33892256
3-Epikatonic acid[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3604.6Standard non polar33892256
3-Epikatonic acid[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O3699.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Epikatonic acid,1TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C3797.2Semi standard non polar33892256
3-Epikatonic acid,1TMS,isomer #2CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@](C)(C(=O)O[Si](C)(C)C)CC[C@]3(C)CC[C@]21C3668.7Semi standard non polar33892256
3-Epikatonic acid,2TMS,isomer #1CC1(C)[C@@H](O[Si](C)(C)C)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@](C)(C(=O)O[Si](C)(C)C)CC[C@]3(C)CC[C@]21C3671.7Semi standard non polar33892256
3-Epikatonic 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]2CC=C2[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C4005.9Semi standard non polar33892256
3-Epikatonic acid,1TBDMS,isomer #2CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)CC[C@]21C3931.5Semi standard non polar33892256
3-Epikatonic 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]2CC=C2[C@@H]3C[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)CC[C@]21C4152.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Epikatonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0016900000-967ca61313ac71cd4ac72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Epikatonic acid GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1001390000-e0c1cf5f330b8f2434b62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Epikatonic acid 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 - 3-Epikatonic acid 10V, Positive-QTOFsplash10-052r-0001900000-c4d1b3183695ce9c7cb12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 20V, Positive-QTOFsplash10-01p6-0016900000-bf145fd83683b979da4d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 40V, Positive-QTOFsplash10-0gbc-1339200000-588e628f03badd5710b72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 10V, Negative-QTOFsplash10-0a4i-0001900000-9a33d3cddaa7c4abc2f42016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 20V, Negative-QTOFsplash10-08fu-0003900000-9c12d3699b3f48ae35fc2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 40V, Negative-QTOFsplash10-000e-2009800000-14a558c2158bc56637442016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 20V, Negative-QTOFsplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 40V, Negative-QTOFsplash10-0a4i-1000900000-c8239ac176478007e3312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 10V, Positive-QTOFsplash10-0a4i-0001900000-ddcec89e34cd9c7fcce92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 20V, Positive-QTOFsplash10-0a4i-0293400000-050ba2d74dc0752c53a32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Epikatonic acid 40V, Positive-QTOFsplash10-00dr-0931000000-7f3f4ac7a0632c032b132021-09-24Wishart 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 IDFDB013179
KNApSAcK IDC00036544
Chemspider ID8609651
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10434225
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1844901
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.