(3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one (CHEM027006)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:26:12 UTC
Update Date2016-11-09 01:18:22 UTC
Accession NumberCHEM027006
Identification
Common Name(3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one
ClassSmall Molecule
Description(3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one is found in mushrooms. (3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one is a constituent of Hypsizygus marmoreus (bunashimeji) and Pleurotus ostreatus (oyster mushroom)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,5a,9a,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-oneGenerator
(3Β,5α,9α,22E,24R)-5,9-epidioxy-3-hydroxyergosta-7,22-dien-6-oneGenerator
4-[(2,5-dioxo-4-Imidazolidinylidene)methyl)-benzaldehydeHMDB
Chemical FormulaC28H42O4
Average Molecular Mass442.631 g/mol
Monoisotopic Mass442.308 g/mol
CAS Registry Number211486-16-7
IUPAC Name8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one
Traditional Name8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one
SMILESCC(C)C(C)\C=C\C(C)C1CCC2C3=CC(=O)C45CC(O)CCC4(C)C3(CCC12C)OO5
InChI IdentifierInChI=1S/C28H42O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h7-8,15,17-22,29H,9-14,16H2,1-6H3/b8-7+
InChI KeyVXKGRYVCJKAYFC-BQYQJAHWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgostane steroids
Alternative Parents
Substituents
  • Ergostane-skeleton
  • Cyclohexenone
  • Ortho-dioxolane
  • Cyclic alcohol
  • Dialkyl peroxide
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0004 g/LALOGPS
logP5.19ALOGPS
logP6ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.23 m³·mol⁻¹ChemAxon
Polarizability51.83 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6014900000-2cfba4e5beb3427b4708Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0075-3211910000-11cce029b15fab19702cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1002900000-48de39352f88089ca2e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055r-9127700000-dd69c79ab779eb48e037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9412000000-9ace1d3e542e4c95398eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-5fc946ff00e50212ecd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-113c16f382c4408257bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-2009300000-ad446e49d256ff5d9c3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0003900000-b8738a42642e32aac8cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aov-9128400000-312ff3568773c28214a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9103100000-68c3573bdd899c9836c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-8ec5474a860abd1cc213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-8ec5474a860abd1cc213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-1006900000-a9ff42a9bf1df8a7c959Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032666
FooDB IDFDB010619
Phenol Explorer IDNot Available
KNApSAcK IDC00012464
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID74886384
ChEBI ID169450
PubChem Compound ID131751275
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM