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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:35 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034224
Secondary Accession Numbers
  • HMDB34224
Metabolite Identification
Common NameDihydrobrassicasterol
DescriptionDihydrobrassicasterol, also known as (3beta)-ergost-5-en-3-ol or 24a-methylcholesterol, 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, dihydrobrassicasterol is considered to be a sterol. Based on a literature review a small amount of articles have been published on Dihydrobrassicasterol.
Structure
Data?1589387733
Synonyms
ValueSource
(3beta)-Ergost-5-en-3-olChEBI
22,23-DihydrobrassicasterolChEBI
(3b)-Ergost-5-en-3-olGenerator
(3Β)-ergost-5-en-3-olGenerator
(24R)-5-Ergosten-3-beta-olHMDB
(24R)-5-Ergosten-3b-olHMDB
(24R)-Ergost-5-en-3-beta-olHMDB
(24R)-Ergost-5-en-3b-olHMDB
(24R)-Methylcholest-5-en-3b-olHMDB
(24S)-beta-Methyl cholesterolHMDB
(3-beta)-Ergost-5-en-3-olHMDB
(3-beta-24R)-Ergost-5-en-3-olHMDB
(3b,24R)-Ergost-5-en-3-olHMDB
24-alpha-MethylcholesterolHMDB
24-Methyl-5-cholestene-3-olHMDB
24-Methylcholest-5-en-3beta-olHMDB
24a-Methyl-5-cholesten-3b-olHMDB
24a-MethylcholesterolHMDB
CampesterinHMDB
CampestrolHMDB
Ergost-5-en-3-beta-olHMDB
Ergost-5-en-3-olHMDB
Ergost-5-en-3 beta- ol, 24 epimerHMDB
24-MethylcholesterolHMDB
Campesterol, (3beta,24xi)-isomerHMDB
24 alpha-Methylcholest-5-en-3 beta-olHMDB
Campesterol, (3beta)-isomerHMDB
CampesterolHMDB
(24S)-Methylcholest-5-en-3beta-olHMDB
(24S)-Methylcholest-5-en-3β-olHMDB
24-EpicampesterolHMDB
24-Methyl-5-cholestene-3beta-olHMDB
24-Methyl-5-cholestene-3β-olHMDB
24S-MethylcholesterolHMDB
24beta-MethylcholesterolHMDB
24Β-methylcholesterolHMDB
Ergost-5-en-3beta-olHMDB
Ergost-5-en-3β-olHMDB
delta22-DihydrobrassicasterolHMDB
delta5-CampesterolHMDB
delta5-ErgostenolHMDB
Δ22-dihydrobrassicasterolHMDB
Δ5-campesterolHMDB
Δ5-ergostenolHMDB
DihydrobrassicasterolHMDB
Chemical FormulaC28H48O
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-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,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number4651-51-8
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@H](C)C(C)C
InChI Identifier
InChI=1S/C28H48O/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/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
InChI KeySGNBVLSWZMBQTH-ZRUUVFCLSA-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
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point157 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00015 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP6.81ALOGPS
logP7.4ChemAxon
logS-7.3ALOGPS
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
Refractivity125.17 m³·mol⁻¹ChemAxon
Polarizability52.41 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]-238.24730932474
DeepCCS[M+Na]+212.43930932474
AllCCS[M+H]+206.632859911
AllCCS[M+H-H2O]+204.632859911
AllCCS[M+NH4]+208.432859911
AllCCS[M+Na]+209.032859911
AllCCS[M-H]-204.732859911
AllCCS[M+Na-2H]-206.732859911
AllCCS[M+HCOO]-209.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydrobrassicasterol[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@H](C)C(C)C2439.1Standard polar33892256
Dihydrobrassicasterol[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@H](C)C(C)C3229.2Standard non polar33892256
Dihydrobrassicasterol[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@H](C)C(C)C3294.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrobrassicasterol,1TMS,isomer #1CC(C)[C@@H](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@@]21C3270.6Semi standard non polar33892256
Dihydrobrassicasterol,1TBDMS,isomer #1CC(C)[C@@H](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@@]21C3494.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrobrassicasterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 10V, Positive-QTOFsplash10-0ue9-1019500000-05a81f76ea60f47816b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 20V, Positive-QTOFsplash10-00lj-7149100000-434088453bcde1b455752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 40V, Positive-QTOFsplash10-000i-8093000000-5277512d6dbbe5d1ce172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 10V, Negative-QTOFsplash10-0002-0009000000-cd4af4f76d04e1cacf462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 20V, Negative-QTOFsplash10-0002-0009000000-4bea7e37de9105dc89052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 40V, Negative-QTOFsplash10-00lr-3019000000-9b243f6f924e30b0b7322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 10V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 20V, Negative-QTOFsplash10-0002-0009000000-f02c317cf088701c56eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 40V, Negative-QTOFsplash10-0002-0009000000-ad5cb5a0f29f4da7cb162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 10V, Positive-QTOFsplash10-0udi-1013900000-5ff92eefb7be32e490d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 20V, Positive-QTOFsplash10-0a4i-9262100000-1079a45f5eba7c1c6da92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrobrassicasterol 40V, Positive-QTOFsplash10-0a5c-9720000000-f4480815d1819a6ecee32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012531
KNApSAcK IDC00023756
Chemspider ID4446730
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283637
PDB IDNot Available
ChEBI ID19809
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1841301
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.