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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:09 UTC
Update Date2022-03-07 02:53:12 UTC
HMDB IDHMDB0032004
Secondary Accession Numbers
  • HMDB32004
Metabolite Identification
Common NameErgostane-3,6-dione
DescriptionErgostane-3,6-dione belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Ergostane-3,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862205
Synonyms
ValueSource
3-(4-Aminobutylamino)propylsulfanylphosphonic acidHMDB
Campestane-3,6-dioneHMDB
Chemical FormulaC28H46O2
Average Molecular Weight414.6636
Monoisotopic Molecular Weight414.349780716
IUPAC Name14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione
Traditional Name14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione
CAS Registry Number88662-00-4
SMILES
CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h17-19,21-25H,7-16H2,1-6H3
InChI KeyVETZNBAGZJYCQT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ecdysteroid
  • 6-oxosteroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility5.5e-05 g/LALOGPS
logP5.71ALOGPS
logP7.09ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)17.77ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.95 m³·mol⁻¹ChemAxon
Polarizability50.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.81431661259
DarkChem[M-H]-193.0131661259
DeepCCS[M-2H]-234.20430932474
DeepCCS[M+Na]+209.45230932474
AllCCS[M+H]+206.832859911
AllCCS[M+H-H2O]+204.832859911
AllCCS[M+NH4]+208.732859911
AllCCS[M+Na]+209.232859911
AllCCS[M-H]-207.032859911
AllCCS[M+Na-2H]-209.032859911
AllCCS[M+HCOO]-211.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ergostane-3,6-dioneCC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C3135.3Standard polar33892256
Ergostane-3,6-dioneCC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C3296.2Standard non polar33892256
Ergostane-3,6-dioneCC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C3419.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ergostane-3,6-dione,1TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(=O)CCC4(C)C3CCC12C3400.8Semi standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(=O)CCC4(C)C3CCC12C3305.5Standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(=O)CCC4(C)C3CCC12C3454.2Semi standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(=O)CCC4(C)C3CCC12C3266.0Standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3474.6Semi standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3338.6Standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3465.4Semi standard non polar33892256
Ergostane-3,6-dione,1TMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3353.7Standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3307.3Semi standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3395.5Standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3453.7Semi standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C)=C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3377.7Standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3390.1Semi standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C3311.7Standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3348.2Semi standard non polar33892256
Ergostane-3,6-dione,2TMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C)C4C=C(O[Si](C)(C)C)CCC4(C)C3CCC12C3299.2Standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC(=O)CCC4(C)C3CCC12C3614.9Semi standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC(=O)CCC4(C)C3CCC12C3565.3Standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC(=O)CCC4(C)C3CCC12C3656.9Semi standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC(=O)CCC4(C)C3CCC12C3444.8Standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3694.4Semi standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3546.0Standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3686.9Semi standard non polar33892256
Ergostane-3,6-dione,1TBDMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3CC(=O)C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3570.0Standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3784.2Semi standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3794.1Standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3896.7Semi standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3779.1Standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3812.4Semi standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #3CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C3640.6Standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3806.9Semi standard non polar33892256
Ergostane-3,6-dione,2TBDMS,isomer #4CC(C)C(C)CCC(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4C=C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3651.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ergostane-3,6-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-3239000000-14917e3db77ded01fe012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergostane-3,6-dione 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 - Ergostane-3,6-dione 10V, Positive-QTOFsplash10-014i-1118900000-8ffe4f7b69d9e9f1dfee2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 20V, Positive-QTOFsplash10-002r-6119100000-1508784fa53940eceded2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 40V, Positive-QTOFsplash10-000i-9117000000-9fb32a2a4ebb0f6560b02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 10V, Negative-QTOFsplash10-03di-0001900000-c1eccd7652115434218e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 20V, Negative-QTOFsplash10-03di-0001900000-967822825051ca30d35d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 40V, Negative-QTOFsplash10-052b-7009000000-e28545ef5f21330ec6752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 10V, Positive-QTOFsplash10-014i-0028900000-358665479b57da721ae42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 20V, Positive-QTOFsplash10-0cdi-9345300000-e0a2549da0f2e4da3c5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 40V, Positive-QTOFsplash10-06rx-9530000000-79bb287fa121413fe3812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 10V, Negative-QTOFsplash10-03di-0000900000-324536fb6b1e1aa9b48c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 20V, Negative-QTOFsplash10-03di-0000900000-b5291f1cacd5c000c5052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergostane-3,6-dione 40V, Negative-QTOFsplash10-03di-0009700000-0f1643d44c2e0ce845b32021-09-24Wishart 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 IDFDB008699
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76380930
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.