Isofucosterol (CHEM023640)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:12:04 UTC
Update Date2016-11-09 01:17:45 UTC
Accession NumberCHEM023640
Identification
Common NameIsofucosterol
ClassSmall Molecule
DescriptionA 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). The double bond at postion 24(28) adopts a Z-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(24Z)-24-Ethylcholesta-5,24(28)-dien-3beta-olChEBI
(24Z)-EthylidenecholesterolChEBI
(3beta)-Stigmasta-5,24(28)-dien-3-olChEBI
(3beta,24Z)-Stigmasta-5,24(28)-dien-3-olChEBI
(Z)-24-Ethylcholesta-5,24(28)-dien-3beta-olChEBI
(Z)-24-EthylidenecholesterolChEBI
(Z)-Stigmasta-5,24(28)-dien-3beta-olChEBI
24Z-Ethylidene-cholest-5-en-3beta-olChEBI
28-IsofucosterolChEBI
Delta(5)-AvenasterolChEBI
delta5-AvenasterolChEBI
(24Z)-24-Ethylcholesta-5,24(28)-dien-3b-olGenerator
(24Z)-24-Ethylcholesta-5,24(28)-dien-3β-olGenerator
(3b)-Stigmasta-5,24(28)-dien-3-olGenerator
(3Β)-stigmasta-5,24(28)-dien-3-olGenerator
(3b,24Z)-Stigmasta-5,24(28)-dien-3-olGenerator
(3Β,24Z)-stigmasta-5,24(28)-dien-3-olGenerator
(Z)-24-Ethylcholesta-5,24(28)-dien-3b-olGenerator
(Z)-24-Ethylcholesta-5,24(28)-dien-3β-olGenerator
(Z)-Stigmasta-5,24(28)-dien-3b-olGenerator
(Z)-Stigmasta-5,24(28)-dien-3β-olGenerator
24Z-Ethylidene-cholest-5-en-3b-olGenerator
24Z-Ethylidene-cholest-5-en-3β-olGenerator
Δ(5)-avenasterolGenerator
Δ5-avenasterolGenerator
(24Z)-Stigmasta-5,24(28)-dien-3-olHMDB
(3.beta.,24Z)-stigmasta-5,24(28)-dien-3-olHMDB
29-IsofucosterolHMDB
FucosterolHMDB, MeSH
IsofucosterolHMDB
24Z-Ethylidenecholest-5-en-3b-olMeSH, HMDB
Fucosterol, 28-(14)C-labeled CPD, (e)-isomerMeSH, HMDB
Stigmasta-5,24-dien-3 beta-olMeSH, HMDB
24-Isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterolMeSH, HMDB
Fucosterol, (3beta)-isomerMeSH, HMDB
(24E)-24-N-PropylidenecholesterolMeSH, HMDB
24(Z)-Ethylidenecholest-5-en-3beta-olHMDB
24(Z)-Ethylidenecholest-5-en-3β-olHMDB
24-Ethylcholesta-5,24(28)Z-dien-3beta-olHMDB
24-Ethylcholesta-5,24(28)Z-dien-3β-olHMDB
Stigmasta-5-cis,24(28)-dien-3beta-olHMDB
Stigmasta-5-cis,24(28)-dien-3β-olHMDB
Chemical FormulaC29H48O
Average Molecular Mass412.691 g/mol
Monoisotopic Mass412.371 g/mol
CAS Registry Number481-14-1
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
SMILESC\C=C(/C(C)C)CC[C@@H](C)[C@H]1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI IdentifierInChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24?,25-,26?,27?,28+,29-/m1/s1
InChI KeyOSELKOCHBMDKEJ-OEDNIQHTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility7.5e-05 g/LALOGPS
logP7.6ALOGPS
logP7.44ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.62 m³·mol⁻¹ChemAxon
Polarizability53.63 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1109000000-109d24725226b225bf0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06di-2104900000-fd4678ce9164cc207101Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-bcaac8318b52fbef2725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6259100000-c5a8fd880d63c55bcacfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7094000000-d9a6cedb0a89fad97057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-82a40a2a370fc124e6efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-96d823e5c0a704f96e3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-7b289abe7c3abd46f650Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1002900000-e69a5278bd381695c11fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e612794ea2c28ad6a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i0c-5169000000-9c2cec3fb85ecb36abafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5d-9320000000-9cc3e8c4c8ef033f50cbSpectrum
MSMass Spectrum (Electron Ionization)splash10-090r-6973000000-3f7408d99c0efb91ca34Spectrum
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 IDHMDB0002374
FooDB IDFDB012493
Phenol Explorer IDNot Available
KNApSAcK IDC00003656
BiGG IDNot Available
BioCyc IDCPD-4127
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsofucosterol
Chemspider ID4444703
ChEBI ID28604
PubChem Compound ID5281326
Kegg Compound IDC08821
YMDB IDNot Available
ECMDB IDM2MDB005964
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1186438
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16481154
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17123816
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24684169
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2775538
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=5343809
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7595097
8. Fernandes P, Cabral JM: Phytosterols: applications and recovery methods. Bioresour Technol. 2007 Sep;98(12):2335-50. Epub 2006 Nov 22.
9. Perona JS, Cabello-Moruno R, Ruiz-Gutierrez V: The role of virgin olive oil components in the modulation of endothelial function. J Nutr Biochem. 2006 Jul;17(7):429-45. Epub 2005 Dec 12.