Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0002374
Secondary Accession Numbers
  • HMDB02374
Metabolite Identification
Common NameIsofucosterol
DescriptionIsofucosterol, also known as delta5-avenasterol, is a phytosterol. Phytosterols, or plant sterols, are compounds that occur naturally and bear a close structural resemblance to cholesterol but have different side-chain configurations. Phytosterols are relevant in pharmaceuticals (production of therapeutic steroids), nutrition (anti-cholesterol additives in functional foods, anti-cancer properties), and cosmetics (creams, lipstick). Phytosterols can be obtained from vegetable oils or from industrial wastes, which gives an added value to the latter. Considerable efforts have been recently dedicated to the development of efficient processes for phytosterol isolation from natural sources. The present work aims to summarize information on the applications of phytosterols and to review recent approaches, mainly from the industry, for the large-scale recovery of phytosterols (PMID: 17123816 , 16481154 ). Isofucosterol is found to be associated with phytosterolemia, which is an inborn error of metabolism.
Structure
Data?1594316387
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 Weight412.702
Monoisotopic Molecular Weight412.370516166
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
CAS Registry Number481-14-1
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C
InChI Identifier
InChI=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-WGMIZEQOSA-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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP10(7.6) g/LALOGPS
logP10(7.44) g/LChemAxon
logS10(-6.7) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.22331661259
DarkChem[M-H]-198.19531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isofucosterol,1TMS,#1C/C=C(/CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3365.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isofucosterol,1TBDMS,#1C/C=C(/CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3591.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isofucosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1109000000-109d24725226b225bf0b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isofucosterol GC-MS (1 TMS) - 70eV, Positivesplash10-06di-2104900000-fd4678ce9164cc2071012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isofucosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-090r-6973000000-3f7408d99c0efb91ca342015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 10V, Positive-QTOFsplash10-01ot-1019500000-bcaac8318b52fbef27252016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 20V, Positive-QTOFsplash10-0002-6259100000-c5a8fd880d63c55bcacf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 40V, Positive-QTOFsplash10-0002-7094000000-d9a6cedb0a89fad970572016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 10V, Negative-QTOFsplash10-03di-0002900000-82a40a2a370fc124e6ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 20V, Negative-QTOFsplash10-03di-0005900000-96d823e5c0a704f96e3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 40V, Negative-QTOFsplash10-0002-2009000000-6ab638e744dcb194bcf22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 20V, Negative-QTOFsplash10-03di-0000900000-7b289abe7c3abd46f6502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 40V, Negative-QTOFsplash10-0a4i-1002900000-e69a5278bd381695c11f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 10V, Positive-QTOFsplash10-000i-0009000000-9e612794ea2c28ad6a2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 20V, Positive-QTOFsplash10-0i0c-5169000000-9c2cec3fb85ecb36abaf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isofucosterol 40V, Positive-QTOFsplash10-0a5d-9320000000-9cc3e8c4c8ef033f50cb2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.45 +/- 0.48 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified106.4 +/- 1.94 uMAdult (>18 years old)BothPhytosterolemia details
Associated Disorders and Diseases
Disease References
Sitosterolemia
  1. Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [PubMed:7595097 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012493
KNApSAcK IDC00003656
Chemspider ID4444703
KEGG Compound IDC08821
BioCyc IDCPD-4127
BiGG IDNot Available
Wikipedia LinkIsofucosterol
METLIN IDNot Available
PubChem Compound5281326
PDB IDNot Available
ChEBI ID28604
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fernandes P, Cabral JM: Phytosterols: applications and recovery methods. Bioresour Technol. 2007 Sep;98(12):2335-50. Epub 2006 Nov 22. [PubMed:17123816 ]
  2. 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. [PubMed:16481154 ]

Enzymes

General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Reactions
5-Dehydroavenasterol → Isofucosteroldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Isofucosterol + NADPH + Hydrogen Ion → beta-Sitosterol + NADPdetails