Sitosterol alpha1 (CHEM016871)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:46:03 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016871
Identification
Common NameSitosterol alpha1
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5alpha)-4-Methylstigmasta-7,24(28)-dien-3-olChEBI
alpha1-SitosterolChEBI
4-alpha-Methyl-5-alpha-stigmasta-7,Z-24-dien-3-beta-olKegg
(Z)-24-EthylidenelophenolKegg
(3b,5a)-4-Methylstigmasta-7,24(28)-dien-3-olGenerator
(3Β,5α)-4-methylstigmasta-7,24(28)-dien-3-olGenerator
a1-SitosterolGenerator
Α1-sitosterolGenerator
4-a-Methyl-5-a-stigmasta-7,Z-24-dien-3-b-olGenerator
4-Α-methyl-5-α-stigmasta-7,Z-24-dien-3-β-olGenerator
(3b,4b,5a)-4-Methylergosta-7,24(28)-dien-3-olGenerator
(3Β,4β,5α)-4-methylergosta-7,24(28)-dien-3-olGenerator
CitrostadienolHMDB
(3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-7,24(28)-dien-3-olHMDB
(3Β,4α,5α,24Z)-4-methylstigmasta-7,24(28)-dien-3-olHMDB
24-EthylidenelophenolHMDB
5alpha-SitosterolHMDB
5Α-sitosterolHMDB
CitrastadienolHMDB
Chemical FormulaC30H50O
Average Molecular Mass426.729 g/mol
Monoisotopic Mass426.386 g/mol
CAS Registry Number474-40-8
IUPAC Name(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,6S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
SMILES[H]\C(C)=C(/CC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])[C@]([H])(C)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)C
InChI IdentifierInChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24-,25+,26+,27+,28+,29-,30+/m1/s1
InChI KeyLPZCCMIISIBREI-JXMPMKKESA-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
  • 3-beta-hydroxysteroid
  • 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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.6e-05 g/LALOGPS
logP7.85ALOGPS
logP7.8ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.09 m³·mol⁻¹ChemAxon
Polarizability55.67 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0012900000-cde59be93f1463ff00e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tb-5239300000-95113b4ddb77ad408fafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pk-8079100000-346450ad4e87290a27caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-2059eb8c355176c1ed29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0001900000-9787c3c5e6e68ec281e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4009600000-8a3e35d1a4792d51fe3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-934040c4df2448e7afa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gdm-3129100000-84658a4c9056d3c8013aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9651000000-2cf44956f81243ef32f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-590c9e4adfdd12b64d93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-43e99e872292ca648e72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1001900000-5af749287f216278536aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033495
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00007321
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7827519
ChEBI ID33203
PubChem Compound ID9548595
Kegg Compound IDC11523
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM