Stigmasterol (CHEM021882)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:43 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021882
Identification
Common NameStigmasterol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,22E)-Stigmasta-5,22-dien-3-olChEBI
5,22-Cholestadien-24-ethyl-3beta-olChEBI
beta-StigmasterolChEBI
PhytosterolChEBI
PoriferasterolChEBI
Stigmasta-5,22-dien-3beta-olChEBI
(3b,22E)-Stigmasta-5,22-dien-3-olGenerator
(3β,22E)-Stigmasta-5,22-dien-3-olGenerator
5,22-Cholestadien-24-ethyl-3b-olGenerator
5,22-Cholestadien-24-ethyl-3β-olGenerator
b-StigmasterolGenerator
β-StigmasterolGenerator
Stigmasta-5,22-dien-3b-olGenerator
Stigmasta-5,22-dien-3β-olGenerator
(24S)-5,22-Stigmastadien-3b-olHMDB
17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
Stigmasta-5,22-dien-3-b-olHMDB
Stigmasta-5,22-dien-3-beta-olHMDB
StigmasterinHMDB
(24S)-24-Ethylcholesta-5,22-dien-3beta-olHMDB
(24S)-24-Ethylcholesta-5,22-dien-3β-olHMDB
(24S)-5,22-Stigmastadien-3beta-olHMDB
(24S)-5,22-Stigmastadien-3β-olHMDB
(24S)-Stigmast-5,22-dien-3beta-olHMDB
(24S)-Stigmast-5,22-dien-3β-olHMDB
24-Ethyl-5,22-cholestadien-3beta-olHMDB
24-Ethyl-5,22-cholestadien-3β-olHMDB
24beta-Ethyl-5,22-cholestadien-3beta-olHMDB
24β-Ethyl-5,22-cholestadien-3β-olHMDB
Stigmasta-5,22(E)-dien-3beta-olHMDB
Stigmasta-5,22(E)-dien-3β-olHMDB
StigmasterolHMDB
delta5,22-Stigmastadien-3beta-olHMDB
delta5-StigmasterolHMDB
Δ5,22-Stigmastadien-3β-olHMDB
Δ5-StigmasterolHMDB
Chemical FormulaC29H48O
Average Molecular Mass412.702 g/mol
Monoisotopic Mass412.371 g/mol
CAS Registry Number83-48-7
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-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,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
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)\C=C\[C@@H](CC)C(C)C
InChI IdentifierInChI=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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyHCXVJBMSMIARIN-PHZDYDNGSA-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
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility2.7e-05 g/LALOGPS
logP6.95ALOGPS
logP7.48ChemAxon
logS-7.2ALOGPS
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
Refractivity130.88 m³·mol⁻¹ChemAxon
Polarizability53.55 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae49Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c313295Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda7530Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e450Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae49Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c313295Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda7530Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e450Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1109000000-be897608aaeab74e5d13Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0avl-2102900000-564b610342ad160ee822Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0000900000-f7738a3fcdee344f82c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-07cs-9400200000-959314bea26c5acd8301Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a59-7900000000-ce066e558ecbe29afea8Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0a4i-3941000000-f854893a9352ff766734Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a59-9720000000-5a3d902c3cd2af078da3Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-053r-7941000000-6c5c63e8c487f86b353bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a59-9731000000-32a70fa14fd448314caaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2019500000-3495ed3a1955cc77528aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9128100000-3c3b91bb2d698a88f9dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8197000000-a80e8fcc32cd4a2dfefeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-322cae85ce921a9ef9e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-d25be97b0cfa1b9bed79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-2019000000-3b119d03e184f575cdc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-2219400000-9acb072e76ff1b8f2e48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-7259000000-a7f52c0e28b61ef2a3acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9320000000-8a54eac3182f86b7095bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-fe3ab0b12c2d51198ed0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1001900000-43dce6fa5af31f5d7958Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a59-8920000000-c7d02c3957677fae28beSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000937
FooDB IDFDB001936
Phenol Explorer IDNot Available
KNApSAcK IDC00023774
BiGG IDNot Available
BioCyc IDCPD-4162
METLIN ID168
PDB IDNot Available
Wikipedia LinkStigmasterol
Chemspider ID4444352
ChEBI ID28824
PubChem Compound ID5280794
Kegg Compound IDC05442
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Geng, Jianguo; Gu, Wenying; Wang, Xiaobao; Gu, Wenying. Method for extraction stigmasterol from mixed sterol of plant. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 6 pp.
2. Noblet JA, Young DL, Zeng EY, Ensari S: Use of fecal steroids to infer the sources of fecal indicator bacteria in the Lower Santa Ana River Watershed, California: sewage is unlikely a significant source. Environ Sci Technol. 2004 Nov 15;38(22):6002-8.
3. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
4. Triana J, Lopez M, Perez FJ, Gonzalez-Platas J, Quintana J, Estevez F, Leon F, Bermejo J: Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities. J Nat Prod. 2005 Apr;68(4):523-31.
5. Valsta LM, Lemstrom A, Ovaskainen ML, Lampi AM, Toivo J, Korhonen T, Piironen V: Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake. Br J Nutr. 2004 Oct;92(4):671-8.
6. Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2.
7. 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.
8. Miettinen TA: Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis. Eur J Clin Invest. 1980 Feb;10(1):27-35.
9. Urech K, Scher JM, Hostanska K, Becker H: Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L. J Pharm Pharmacol. 2005 Jan;57(1):101-9.
10. Morin RJ, Elms NJ: Rapid microanalysis of cholesterol in bile and serum by gas chromatography. Ann Clin Lab Sci. 1975 Jan-Feb;5(1):52-6.
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=13318319
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=13547565