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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:45 UTC
HMDB IDHMDB00494
Secondary Accession NumbersNone
Metabolite Identification
Common NameStigmastanol
DescriptionStigmastanol is plant stanol. It can decrease the circulating LDL-cholesterol level by reducing intestinal cholesterol absorption. (PMID 16910223 ).
Structure
Thumb
Synonyms
ValueSource
(3b)-Stigmastan-3-olHMDB
(3beta)-Stigmastan-3-olHMDB
(3beta,5alpha)-Stigmastan-3-olHMDB
24-alpha-EthylcholestanolHMDB
24a-EthylcholestanolHMDB
4a-Methyl-5a,14a-lumistan-3b-olHMDB
4a-MethylcampestanolHMDB
5,6-dihydro-b-SitosterolHMDB
5,6-dihydro-beta-SitosterolHMDB
5a-Stigmastan-3b-olHMDB
5alpha-Stigmastan-3beta-olHMDB
b-SitostanolHMDB
beta-dihydro-SitosterolHMDB
beta-SitostanolHMDB
dihydro-b-SitosterolHMDB
dihydro-beta-SitosterolHMDB
DihydrositosterinHMDB
DihydrositosterolHMDB
FucostanolHMDB
SitostanolHMDB
SpinastanolHMDB
Stigmastan-3-olHMDB
Stigmastane-3-beta-olHMDB
Chemical FormulaC29H52O
Average Molecular Weight416.7226
Monoisotopic Molecular Weight416.401816286
IUPAC Name(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Namestigmastane-3-β-ol
CAS Registry Number83-45-4
SMILES
[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyInChIKey=LGJMUZUPVCAVPU-KZXGMYDKSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Stigmastane-skeleton
  • C24-propyl-sterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Nucleus
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.14e-05 mg/mLALOGPS
logP7.23ALOGPS
logP8.25ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.92 m3·mol-1ChemAxon
Polarizability54.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-066u-4942100000-604c3357e69c5eff6d37View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Nucleus
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Skeletal Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.8 +/- 8.8 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified168.0 +/- 2.8 uMAdult (>18 years old)BothPhytosterolemia details
Associated Disorders and Diseases
Disease References
Sitosterolemia
  1. Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [7595097 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001305
KNApSAcK IDC00032163
Chemspider ID13078158
KEGG Compound IDNot Available
BioCyc IDCPD-8481
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00494
Metagene LinkHMDB00494
METLIN ID425
PubChem Compound15559396
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBengtsson, B. E. A comparison between sitostanol and stigmastanol. Z. physiol. Chem. (1935), 237 46-51.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Miller TR, Anderson RJ, Linas SL, Henrich WL, Berns AS, Gabow PA, Schrier RW: Urinary diagnostic indices in acute renal failure: a prospective study. Ann Intern Med. 1978 Jul;89(1):47-50. [666184 ]
  2. Connor WE, Lin DS, Pappu AS, Frohlich J, Gerhard G: Dietary sitostanol and campestanol: accumulation in the blood of humans with sitosterolemia and xanthomatosis and in rat tissues. Lipids. 2005 Sep;40(9):919-23. [16331855 ]
  3. Skrede B, Bjorkhem I, Bergesen O, Kayden HJ, Skrede S: The presence of 5 alpha-sitostanol in the serum of a patient with phytosterolemia, and its biosynthesis from plant steroids in rats with bile fistula. Biochim Biophys Acta. 1985 Oct 2;836(3):368-75. [4041477 ]
  4. Devaraj S, Jialal I: The role of dietary supplementation with plant sterols and stanols in the prevention of cardiovascular disease. Nutr Rev. 2006 Jul;64(7 Pt 1):348-54. [16910223 ]
  5. Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [10517218 ]
  6. Trump DL: Serious hyponatremia in patients with cancer: management with demeclocycline. Cancer. 1981 Jun 15;47(12):2908-12. [6790160 ]
  7. Ostlund RE Jr, Spilburg CA, Stenson WF: Sitostanol administered in lecithin micelles potently reduces cholesterol absorption in humans. Am J Clin Nutr. 1999 Nov;70(5):826-31. [10539742 ]