Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2019-11-26 02:56:18 UTC
Primary IDFDB001315
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsofucosterol
DescriptionIsofucosterol 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. Isofucosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number481-14-1
Structure
Thumb
Synonyms
SynonymSource
(24Z)-Ethylidenecholesterolbiospider
(24Z)-Stigmasta-5,24(28)-dien-3-olHMDB
(3.beta.,24Z)-stigmasta-5,24(28)-dien-3-olHMDB
(3b,24Z)-Stigmasta-5,24(28)-dien-3-olbiospider
(Z)-24-Ethylidenecholesterolbiospider
(Z)-Stigmasta-5,24(28)-dien-3β-olbiospider
(Z)-Stigmasta-5,24(28)-dien-3b-olbiospider
29-IsofucosterolHMDB
29-Isofucosterol (7CI)manual
cis-24-Ethylidenecholesterolmanual
cis-D5-Avenosterolmanual
Isofucosteroldb_source
Stigmasta-5,24(28)-dien-3β-ol, (Z)-biospider
δ5-avenasterolGenerator
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
Polarizability53.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H48O
IUPAC name(2R,5S,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
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
Isomeric SMILESC\C=C(/C(C)C)CC[C@@H](C)[C@H]1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.40%; H 11.72%; O 3.88%DFC
Melting PointMp 137° (130-131°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -37.6 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-bcaac8318b52fbef2725Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6259100000-c5a8fd880d63c55bcacfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7094000000-d9a6cedb0a89fad97057Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-82a40a2a370fc124e6efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-96d823e5c0a704f96e3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf2Spectrum
NMRNot Available
ChemSpider ID4444703
ChEMBL IDCHEMBL1836654
KEGG Compound IDC08821
Pubchem Compound ID5281326
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02374
CRC / DFC (Dictionary of Food Compounds) IDHHL06-C:BZK94-E
EAFUS IDNot Available
Dr. Duke ID29-ISOFUCOSTEROL|28-ISOFUCOSTEROL|ISOFUCOSTEROL|24Z-ETHYLIDENECHOLESTEROL
BIGG IDNot Available
KNApSAcK IDC00003656
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
7-dehydrocholesterol reductaseDHCR7Q9UBM7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.