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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000494
Secondary Accession Numbers
  • HMDB00494
Metabolite Identification
Common NameStigmastanol
DescriptionStigmastanol, also known as sitostanol or (3b)-stigmastan-3-ol, belongs to stigmastanes and derivatives class of compounds. Those 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. Stigmastanol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Stigmastanol can be found primarily in blood and feces, as well as in human skeletal muscle tissue. Stigmastanol can be found anywhere throughout the human cell, such as in in the peroxisome, in the cytoplasm, in the Golgi apparatus, and in the membrane (predicted from logP). It can also be found in the extracellular space. Moreover, stigmastanol is found to be associated with sitosterolemia, an inborn error of metabolism. Stigmastanol (sitostanol) is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmastanol inhibits the absorption of cholesterol from the diet. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver (Wikipedia). Stigmastanol is plant stanol. It can decrease the circulating LDL-cholesterol level by reducing intestinal cholesterol absorption (PMID 16910223 ).
Structure
Data?1582752135
Synonyms
ValueSource
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylateChEBI
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylateGenerator
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylic acidGenerator
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acidGenerator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylateGenerator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylic acidGenerator
(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, MeSH
dihydro-b-SitosterolHMDB
dihydro-beta-SitosterolHMDB
DihydrositosterinHMDB
DihydrositosterolHMDB, MeSH
FucostanolHMDB
SitostanolHMDB, MeSH
SpinastanolHMDB
Stigmastan-3-olHMDB
Stigmastane-3-beta-olHMDB
24 alpha-Ethyl-5 alpha-cholestan-3 beta-olMeSH, HMDB
Stigmastanol, (3beta,5beta,24S)-isomerMeSH, HMDB
24 alpha-Ethyl-5 beta-cholestan-3 alpha-olMeSH, HMDB
StigmastanolMeSH
Chemical FormulaC29H52O
Average Molecular Weight416.734
Monoisotopic Molecular Weight416.401816294
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
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
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 KeyLGJMUZUPVCAVPU-KZXGMYDKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
Substituents
  • Ajmalicine-skeleton
  • 18-oxayohimban
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.92 m³·mol⁻¹ChemAxon
Polarizability54.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.74231661259
DarkChem[M-H]-198.8331661259
AllCCS[M+H]+210.52932859911
AllCCS[M-H]-203.81132859911
DeepCCS[M-2H]-239.15330932474
DeepCCS[M+Na]+213.40230932474
AllCCS[M+H]+210.532859911
AllCCS[M+H-H2O]+208.732859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.732859911
AllCCS[M-H]-203.832859911
AllCCS[M+Na-2H]-206.132859911
AllCCS[M+HCOO]-208.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
StigmastanolCC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C2281.7Standard polar33892256
StigmastanolCC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C3319.8Standard non polar33892256
StigmastanolCC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C3443.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stigmastanol,1TMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3333.1Semi standard non polar33892256
Stigmastanol,1TBDMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3551.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Stigmastanol GC-MS (1 TMS)splash10-066u-4942100000-604c3357e69c5eff6d372014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized)splash10-066u-4942100000-604c3357e69c5eff6d372017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-2109200000-a86730d94764ca5efe852017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmastanol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3103900000-2af97f9cf8a2adff31962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmastanol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 10V, Positive-QTOFsplash10-00kb-0019600000-d66897ecdbe2fe8455082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 20V, Positive-QTOFsplash10-0002-4149200000-b304e7e4678a4df85f022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 40V, Positive-QTOFsplash10-0002-8089100000-404a21c90ecdfcc88b6b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 10V, Negative-QTOFsplash10-014i-0002900000-5b14a67727dfd30debe92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 20V, Negative-QTOFsplash10-014i-0004900000-af8991b83701d4b9f0812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 40V, Negative-QTOFsplash10-0012-1009000000-eebc7b9b36cf260dbceb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 10V, Negative-QTOFsplash10-014i-0000900000-b5f23f2410b0642246b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 20V, Negative-QTOFsplash10-014i-0000900000-bb6fb31d418e3fc0bd502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 40V, Negative-QTOFsplash10-02ta-0004900000-0b0cca9041a827eb22382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 10V, Positive-QTOFsplash10-014i-2125900000-88705afd06ff3d3ec2772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 20V, Positive-QTOFsplash10-014i-9022300000-71d6fc93ae624cc61e6c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmastanol 40V, Positive-QTOFsplash10-0a4i-9610000000-0304da0e562e0b20612f2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Nucleus
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.8 +/- 8.8 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified168.0 +/- 2.8 uMAdult (>18 years old)BothPhytosterolemia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer 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. [PubMed:7595097 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00025214
Chemspider IDNot Available
KEGG Compound IDC11682
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72340
PDB IDNot Available
ChEBI ID9479
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10517218 ]
  6. Trump DL: Serious hyponatremia in patients with cancer: management with demeclocycline. Cancer. 1981 Jun 15;47(12):2908-12. [PubMed: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. [PubMed:10539742 ]