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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:46 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033873
Secondary Accession Numbers
  • HMDB33873
Metabolite Identification
Common Namealpha-Spinasterol
Descriptionalpha-Spinasterol, also known as α-spinasterol, 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. Based on a literature review a small amount of articles have been published on alpha-Spinasterol.
Structure
Data?1563862474
Synonyms
ValueSource
a-SpinasterolGenerator
Α-spinasterolGenerator
SpinasterolMeSH
Spinasterol, (3beta,5alpha,22E,24R)-isomerMeSH
(-)-SpinasterolHMDB
(3-beta,5-alpha,22E)-Stigmasta-7,22-dien-3-olHMDB
(e)-5-alpha-Stigmasta-7,22-dien-3-beta-olHMDB
.alpha-spinasterinHMDB
alpha-SpinasterinHMDB
BessisterolHMDB
HitodesterolHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name14-[(3E)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Namechondrillasterol
CAS Registry Number481-18-5
SMILES
CCC(\C=C\C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)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/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3/b9-8+
InChI KeyJZVFJDZBLUFKCA-CMDGGOBGSA-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
  • Triterpenoid
  • Stigmastane-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point171 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.4e-05 g/LALOGPS
logP7.46ALOGPS
logP7.48ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.88 m³·mol⁻¹ChemAxon
Polarizability51.99 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
DarkChem[M+H]+198.64931661259
DarkChem[M-H]-198.64131661259
DeepCCS[M-2H]-237.96330932474
DeepCCS[M+Na]+213.19130932474
AllCCS[M+H]+208.832859911
AllCCS[M+H-H2O]+206.732859911
AllCCS[M+NH4]+210.732859911
AllCCS[M+Na]+211.232859911
AllCCS[M-H]-205.332859911
AllCCS[M+Na-2H]-207.532859911
AllCCS[M+HCOO]-209.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-SpinasterolCCC(\C=C\C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)C(C)C3045.4Standard polar33892256
alpha-SpinasterolCCC(\C=C\C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)C(C)C3117.6Standard non polar33892256
alpha-SpinasterolCCC(\C=C\C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)C(C)C3250.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Spinasterol,1TMS,isomer #1CCC(/C=C/C(C)C1CCC2C3=CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C)C(C)C3363.4Semi standard non polar33892256
alpha-Spinasterol,1TBDMS,isomer #1CCC(/C=C/C(C)C1CCC2C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C)C(C)C3598.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Spinasterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1019000000-9f40d5e104e28b74f47f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Spinasterol GC-MS (1 TMS) - 70eV, Positivesplash10-0avl-2102900000-fd9cf3134624a7124e512017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Spinasterol 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 - alpha-Spinasterol 10V, Positive-QTOFsplash10-01ot-2119500000-458321b197191df3cfa82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 20V, Positive-QTOFsplash10-0002-9137100000-02a7ee61917940e6e8d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 40V, Positive-QTOFsplash10-0002-9173000000-98164d4886a8c1b280f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 10V, Negative-QTOFsplash10-03di-0002900000-5dece0872b39d99790332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 20V, Negative-QTOFsplash10-03di-0005900000-7d6c2707e11b1c9764892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 40V, Negative-QTOFsplash10-0002-3009000000-776a6612a50c39db2a6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 20V, Negative-QTOFsplash10-03di-0000900000-a99341cfcea792fa61a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 40V, Negative-QTOFsplash10-0btc-0019700000-db3dfeb990b5d4a17b8b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 10V, Positive-QTOFsplash10-03di-2127900000-98cf3cc692c171d2054e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 20V, Positive-QTOFsplash10-06si-9225100000-5de92c1e2c9df6c944a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Spinasterol 40V, Positive-QTOFsplash10-0bta-9720000000-19761d81ab9ba750e7f92021-09-22Wishart 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 IDFDB012065
KNApSAcK IDC00003673
Chemspider ID4474578
KEGG Compound IDC08840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315190
PDB IDNot Available
ChEBI ID173035
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. 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.