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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:03:55 UTC
Update Date2022-03-07 02:54:44 UTC
HMDB IDHMDB0036001
Secondary Accession Numbers
  • HMDB36001
Metabolite Identification
Common NameEpoxyganoderiol A
DescriptionEpoxyganoderiol A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Epoxyganoderiol A is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862805
SynonymsNot Available
Chemical FormulaC30H48O4
Average Molecular Weight472.6997
Monoisotopic Molecular Weight472.355260024
IUPAC Name9-hydroxy-14-{4-[3-(hydroxymethyl)-3-methyloxiran-2-yl]butan-2-yl}-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one
Traditional Name9-hydroxy-14-{4-[3-(hydroxymethyl)-3-methyloxiran-2-yl]butan-2-yl}-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one
CAS Registry Number114020-56-3
SMILES
CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O
InChI Identifier
InChI=1S/C30H48O4/c1-18(8-9-24-30(7,17-31)34-24)19-10-15-29(6)25-20(11-14-28(19,29)5)27(4)13-12-23(33)26(2,3)22(27)16-21(25)32/h18-19,21-22,24,31-32H,8-17H2,1-7H3
InChI KeyXRLVMZVXPMYCSF-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP5.25ALOGPS
logP5.01ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.29ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.62 m³·mol⁻¹ChemAxon
Polarizability56.52 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]+211.90231661259
DarkChem[M-H]-204.65531661259
DeepCCS[M-2H]-246.25230932474
DeepCCS[M+Na]+221.59630932474
AllCCS[M+H]+218.232859911
AllCCS[M+H-H2O]+216.532859911
AllCCS[M+NH4]+219.732859911
AllCCS[M+Na]+220.232859911
AllCCS[M-H]-214.232859911
AllCCS[M+Na-2H]-216.832859911
AllCCS[M+HCOO]-219.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epoxyganoderiol ACC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O2766.2Standard polar33892256
Epoxyganoderiol ACC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O3413.8Standard non polar33892256
Epoxyganoderiol ACC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O3893.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epoxyganoderiol A,1TMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O3813.1Semi standard non polar33892256
Epoxyganoderiol A,1TMS,isomer #2CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O[Si](C)(C)C3829.3Semi standard non polar33892256
Epoxyganoderiol A,1TMS,isomer #3CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C)C(C)(C)C1CC3O3748.2Semi standard non polar33892256
Epoxyganoderiol A,2TMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O[Si](C)(C)C3819.2Semi standard non polar33892256
Epoxyganoderiol A,2TMS,isomer #2CC(CCC1OC1(C)CO[Si](C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C)C(C)(C)C1CC3O3789.7Semi standard non polar33892256
Epoxyganoderiol A,2TMS,isomer #3CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C3705.5Semi standard non polar33892256
Epoxyganoderiol A,3TMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C3713.2Semi standard non polar33892256
Epoxyganoderiol A,3TMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C3458.6Standard non polar33892256
Epoxyganoderiol A,1TBDMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O4047.9Semi standard non polar33892256
Epoxyganoderiol A,1TBDMS,isomer #2CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O[Si](C)(C)C(C)(C)C4039.3Semi standard non polar33892256
Epoxyganoderiol A,1TBDMS,isomer #3CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC3O3979.2Semi standard non polar33892256
Epoxyganoderiol A,2TBDMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(=O)C(C)(C)C1CC3O[Si](C)(C)C(C)(C)C4253.5Semi standard non polar33892256
Epoxyganoderiol A,2TBDMS,isomer #2CC(CCC1OC1(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC3O4241.0Semi standard non polar33892256
Epoxyganoderiol A,2TBDMS,isomer #3CC(CCC1OC1(C)CO)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C(C)(C)C4127.7Semi standard non polar33892256
Epoxyganoderiol A,3TBDMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C(C)(C)C4359.3Semi standard non polar33892256
Epoxyganoderiol A,3TBDMS,isomer #1CC(CCC1OC1(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(C)C3=C(CCC12C)C1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC3O[Si](C)(C)C(C)(C)C3964.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyganoderiol A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-1225900000-305c68bb0b200b5dbf362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyganoderiol A GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-3401349000-8ba641406ae6301746742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyganoderiol A 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 - Epoxyganoderiol A 10V, Positive-QTOFsplash10-0ab9-0002900000-4e8d7df91ab86403faa02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 20V, Positive-QTOFsplash10-052s-1128900000-34bdaea117805411faed2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 40V, Positive-QTOFsplash10-0api-2049300000-83d1e16c1e0ddecd7f0b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 10V, Negative-QTOFsplash10-00di-0000900000-1a146d5f3bf6c700cad92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 20V, Negative-QTOFsplash10-0fk9-1000900000-2a6e59fc3875ceb543342016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 40V, Negative-QTOFsplash10-0a4i-9000500000-2395f2a1dc7b44a268e12016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 10V, Negative-QTOFsplash10-0fk9-0000900000-52c2ab4785bc4b7e2d342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 20V, Negative-QTOFsplash10-00di-1001900000-71d261212d42488590722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 40V, Negative-QTOFsplash10-0002-0009800000-a11bbe6b05369b28795f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 10V, Positive-QTOFsplash10-05fs-0105900000-80f2a159672173bd3f3a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 20V, Positive-QTOFsplash10-002b-0409800000-5db21fcb7ecdd72d53cb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyganoderiol A 40V, Positive-QTOFsplash10-0zp0-4589100000-760011d4874d741e30da2021-09-25Wishart 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 IDFDB014810
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14015434
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.