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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-10-30 13:54:46 UTC
Update Date2020-04-22 22:55:00 UTC
HMDB IDHMDB0011181
Secondary Accession Numbers
  • HMDB11181
Metabolite Identification
Common NameBrassicasterol
DescriptionBrassicasterol 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. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343 ).
Structure
Data?1587596100
Synonyms
ValueSource
24 beta-Methylcholesta-5,22-dien-3 beta-olMeSH
Ergosta-5,22-dien-3 beta-olMeSH
trans-22-DehydrocampestrolMeSH
EpibrassicasterolMeSH
(22E,24R)-24-Methylcholesta-5,22-dien-3beta-olChEBI
(3beta,22E)-Ergosta-5,22-dien-3-olChEBI
24(R)-Methylcholesta-5,22E-dien-3beta-olChEBI
24-Methyl cholest-5,22-dien-3beta-olChEBI
BrassicasterinChEBI
Ergosta-5,22(E)-dien-3beta-olChEBI
Ergosta-5,22E-dien-3beta-olChEBI
(22E,24R)-24-Methylcholesta-5,22-dien-3b-olGenerator
(22E,24R)-24-Methylcholesta-5,22-dien-3β-olGenerator
(3b,22E)-Ergosta-5,22-dien-3-olGenerator
(3β,22E)-Ergosta-5,22-dien-3-olGenerator
24(R)-Methylcholesta-5,22E-dien-3b-olGenerator
24(R)-Methylcholesta-5,22E-dien-3β-olGenerator
24-Methyl cholest-5,22-dien-3b-olGenerator
24-Methyl cholest-5,22-dien-3β-olGenerator
Ergosta-5,22(e)-dien-3b-olGenerator
Ergosta-5,22(E)-dien-3β-olGenerator
Ergosta-5,22E-dien-3b-olGenerator
Ergosta-5,22E-dien-3β-olGenerator
(22E,24R)-Ergosta-5,22-dien-3beta-olHMDB
(22E,24R)-Ergosta-5,22-dien-3β-olHMDB
24-Methylcholesta-5,22-dien-3beta-olHMDB
24-Methylcholesta-5,22-dien-3β-olHMDB
BrassicasterolHMDB
Ergosta-5,22-dien-3beta-olHMDB
Ergosta-5,22-dien-3β-olHMDB
delta5,22-Ergostadien-3beta-olHMDB
delta5,22-ErgostadienolHMDB
Δ5,22-Ergostadien-3β-olHMDB
Δ5,22-ErgostadienolHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.675
Monoisotopic Molecular Weight398.354866101
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[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,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number474-67-9
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)\C=C\[C@H](C)C(C)C
InChI Identifier
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
InChI KeyOILXMJHPFNGGTO-ZAUYPBDWSA-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-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.5e-05 g/LALOGPS
logP6.48ALOGPS
logP7.04ChemAxon
logS-7.1ALOGPS
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 Count4ChemAxon
Refractivity126.28 m³·mol⁻¹ChemAxon
Polarizability51.72 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-1009000000-2cdde804050dbfee5390Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9027000000-a9b112b13d88d82504f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9075000000-31bcbfe73d3e813dea2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e596d0ca2d13e8489dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-c55e819a24a5d992d0adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2019000000-18730215400fcc19dfaaSpectrum
MSMass Spectrum (Electron Ionization)splash10-0aor-9841000000-108cc074531f4bde545aSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.57 (0.25-1.8) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012496
KNApSAcK IDC00003646
Chemspider ID4444704
KEGG Compound IDC08813
BioCyc IDCPD-4161
BiGG IDNot Available
Wikipedia LinkBrassicasterol
METLIN IDNot Available
PubChem Compound5281327
PDB IDNot Available
ChEBI ID3168
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. Vanmierlo T, Popp J, Kolsch H, Friedrichs S, Jessen F, Stoffel-Wagner B, Bertsch T, Hartmann T, Maier W, von Bergmann K, Steinbusch H, Mulder M, Lutjohann D: The plant sterol brassicasterol as additional CSF biomarker in Alzheimer's disease. Acta Psychiatr Scand. 2011 Sep;124(3):184-92. doi: 10.1111/j.1600-0447.2011.01713.x. Epub 2011 May 17. [PubMed:21585343 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.