(3beta,5alpha,6alpha,7beta,14alpha,22E,24R)-5,6-Epoxyergosta-8,22-diene-3,7,14-triol (CHEM027029)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:27:05 UTC
Update Date2016-11-09 01:18:22 UTC
Accession NumberCHEM027029
Identification
Common Name(3beta,5alpha,6alpha,7beta,14alpha,22E,24R)-5,6-Epoxyergosta-8,22-diene-3,7,14-triol
ClassSmall Molecule
DescriptionConstituent of Lentinus edodes (shiitake). (3beta,5alpha,6alpha,7beta,14alpha,22E,24R)-5,6-Epoxyergosta-8,22-diene-3,7,14-triol is found in mushrooms.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,5a,6a,7b,14a,22E,24R)-5,6-Epoxyergosta-8,22-diene-3,7,14-triolGenerator
(3Β,5α,6α,7β,14α,22E,24R)-5,6-epoxyergosta-8,22-diene-3,7,14-triolGenerator
Chemical FormulaC28H44O4
Average Molecular Mass444.647 g/mol
Monoisotopic Mass444.324 g/mol
CAS Registry Number211486-18-9
IUPAC Name15-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10,12-triol
Traditional Name15-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10,12-triol
SMILESCC(C)C(C)\C=C\C(C)C1CCC2(O)C3=C(CCC12C)C1(C)CCC(O)CC11OC1C3O
InChI IdentifierInChI=1S/C28H44O4/c1-16(2)17(3)7-8-18(4)20-11-14-27(31)22-21(10-13-25(20,27)5)26(6)12-9-19(29)15-28(26)24(32-28)23(22)30/h7-8,16-20,23-24,29-31H,9-15H2,1-6H3/b8-7+
InChI KeyPEFVSALFOVYKAA-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 ParentsNot Available
SubstituentsNot Available
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 Solubility0.017 g/LALOGPS
logP3.92ALOGPS
logP3.93ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)13.25ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.93 m³·mol⁻¹ChemAxon
Polarizability52.64 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p0-2375900000-6c41e7c7bd476b9f8cdeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-3100029000-e1958a43118749067d98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-1001900000-03398ee4696850e8e81eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057r-9208700000-896bd28068c73e209788Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m3-9013100000-a50fc409b67db2a83886Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-00fb75657e19de4aa943Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0000900000-6a58b50d5669172242dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00w9-2129400000-06e60cb9be956e879977Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9106800000-fdfe26bdfa5219a6a46aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9101000000-d02a5e4ee36cd0e132eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9200000000-9938245d2e76dd62017eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-4a1a4016cf02e8b45f39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-4a1a4016cf02e8b45f39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0201900000-8a8d83e33c8d8ea0797cSpectrum
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 IDHMDB0032691
FooDB IDFDB010648
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751285
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