(3beta,5alpha,6alpha,22E,24R)-Ergosta-7,9(11),22-triene-3,5,6-triol (CHEM026891)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:18:26 UTC
Update Date2016-11-09 01:18:21 UTC
Accession NumberCHEM026891
Identification
Common Name(3beta,5alpha,6alpha,22E,24R)-Ergosta-7,9(11),22-triene-3,5,6-triol
ClassSmall Molecule
Description(3beta,5alpha,6beta,22E,24R)-Ergosta-7,9(11),22-triene-3,5,6-triol is found in mushrooms. (3beta,5alpha,6beta,22E,24R)-Ergosta-7,9(11),22-triene-3,5,6-triol is a constituent of Grifola frondosa (maitake)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,5a,6a,22E,24R)-Ergosta-7,9(11),22-triene-3,5,6-triolGenerator
(3Β,5α,6α,22E,24R)-ergosta-7,9(11),22-triene-3,5,6-triolGenerator
Chemical FormulaC28H44O3
Average Molecular Mass428.647 g/mol
Monoisotopic Mass428.329 g/mol
CAS Registry Number71097-07-9
IUPAC Name14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-diene-5,7,8-triol
Traditional Name14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-diene-5,7,8-triol
SMILESCC(C)C(C)\C=C\C(C)C1CCC2C3=CC(O)C4(O)CC(O)CCC4(C)C3=CCC12C
InChI IdentifierInChI=1S/C28H44O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,12,15,17-20,22-23,25,29-31H,9-11,13-14,16H2,1-6H3/b8-7+
InChI KeyFMEOHNKBCMQEEH-BQYQJAHWSA-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
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.0095 g/LALOGPS
logP5.08ALOGPS
logP4.48ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity129.82 m³·mol⁻¹ChemAxon
Polarizability52.06 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-07w9-0109200000-33a5f643423b4865bfcaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0059-2000039000-2699bf0de6013861046eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1004900000-a639f1f34e0a5996c39cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-8029400000-d98662795207bd989c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-9044000000-0efe095a8ed942cf3e63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-55d5a9af617dd3cb43c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0001900000-8d7c80c4a60bd5f579c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03yj-3019400000-5ce9c074a4978a6cf6f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0017900000-fb5b2c6288caf47c7143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kdi-9158500000-637a5ad945a31f6cea94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9421000000-ea27498b0f24d247da61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-a509d4af6bebc9e05806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-aa84c8d2891f8e6bb80fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009700000-fa5a95f0bf5ee82f3bfaSpectrum
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 IDHMDB0032108
FooDB IDFDB008830
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 ID190003
PubChem Compound ID131751260
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