Hmdb loader
Survey
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 Date2008-10-30 13:54:46 UTC
Update Date2022-03-07 02:51:03 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
(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
24 beta-Methylcholesta-5,22-dien-3 beta-olHMDB
Ergosta-5,22-dien-3 beta-olHMDB
trans-22-DehydrocampestrolHMDB
EpibrassicasterolHMDB
(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
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
BrassicasterolHMDB
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 - 151 °CNot Available
Boiling Point488.00 to 489.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00023 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.679 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-239.18230932474
DeepCCS[M+Na]+213.38130932474
AllCCS[M+H]+205.732859911
AllCCS[M+H-H2O]+203.532859911
AllCCS[M+NH4]+207.732859911
AllCCS[M+Na]+208.232859911
AllCCS[M-H]-205.132859911
AllCCS[M+Na-2H]-207.032859911
AllCCS[M+HCOO]-209.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Brassicasterol[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)C2562.6Standard polar33892256
Brassicasterol[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)C3192.5Standard non polar33892256
Brassicasterol[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)C3202.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Brassicasterol,1TMS,isomer #1CC(C)[C@@H](C)/C=C/[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@@]21C3234.2Semi standard non polar33892256
Brassicasterol,1TBDMS,isomer #1CC(C)[C@@H](C)/C=C/[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@@]21C3459.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brassicasterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0aor-9841000000-108cc074531f4bde545a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 10V, Positive-QTOFsplash10-001j-1009000000-2cdde804050dbfee53902019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 20V, Positive-QTOFsplash10-001i-9027000000-a9b112b13d88d82504f22019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 40V, Positive-QTOFsplash10-001r-9075000000-31bcbfe73d3e813dea2d2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 10V, Negative-QTOFsplash10-0002-0009000000-e596d0ca2d13e8489dac2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 20V, Negative-QTOFsplash10-0002-0009000000-c55e819a24a5d992d0ad2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 40V, Negative-QTOFsplash10-001i-2019000000-18730215400fcc19dfaa2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 20V, Negative-QTOFsplash10-0002-0009000000-98dfe229433f1d54d64c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 40V, Negative-QTOFsplash10-0002-0009000000-bb8f075b2dcda97b2fce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 10V, Positive-QTOFsplash10-0002-1029000000-599c0145128a3ccee8ee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 20V, Positive-QTOFsplash10-0aw9-9175000000-ae65db6d5bbb186481c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassicasterol 40V, Positive-QTOFsplash10-000x-9510000000-e6c1163389b6c080d7c02021-09-22Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1589891
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.