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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0000937
Secondary Accession Numbers
  • HMDB00937
Metabolite Identification
Common NameStigmasterol
DescriptionStigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism.
Structure
Data?1601231659
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 Weight412.702
Monoisotopic Molecular Weight412.370516166
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
CAS Registry Number83-48-7
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 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/h8-10,19-21,23-27,30H,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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.7e-05 g/LALOGPS
logP10(6.95) g/LALOGPS
logP10(7.48) g/LChemAxon
logS10(-7.2) g/LALOGPS
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
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]+199.57431661259
DarkChem[M-H]-199.95531661259
AllCCS[M+H]+208.77132859911
AllCCS[M-H]-205.34132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Stigmasterol[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)C2595.3Standard polar33892256
Stigmasterol[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)C3304.4Standard non polar33892256
Stigmasterol[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)C3316.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stigmasterol,1TMS,isomer #1CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3323.8Semi standard non polar33892256
Stigmasterol,1TBDMS,isomer #1CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3554.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae492017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c3132952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda75302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e4502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae492018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c3132952018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda75302018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Stigmasterol EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e4502018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmasterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1109000000-be897608aaeab74e5d132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmasterol GC-MS (1 TMS) - 70eV, Positivesplash10-0avl-2102900000-564b610342ad160ee8222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmasterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmasterol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a59-8920000000-c7d02c3957677fae28be2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-03di-0000900000-f7738a3fcdee344f82c92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-07cs-9400200000-959314bea26c5acd83012012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0a59-7900000000-ce066e558ecbe29afea82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol EI-B (SHIMADZU LKB-9000B) , Positive-QTOFsplash10-0a4i-3941000000-f854893a9352ff7667342012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol EI-B (Unknown) , Positive-QTOFsplash10-0a59-9720000000-5a3d902c3cd2af078da32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol EI-B (HITACHI RMU-6E) , Positive-QTOFsplash10-053r-7941000000-6c5c63e8c487f86b353b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stigmasterol EI-B (HITACHI M-60) , Positive-QTOFsplash10-0a59-9731000000-32a70fa14fd448314caa2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 10V, Positive-QTOFsplash10-01ot-2019500000-3495ed3a1955cc77528a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 20V, Positive-QTOFsplash10-0002-9128100000-3c3b91bb2d698a88f9db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 40V, Positive-QTOFsplash10-0002-8197000000-a80e8fcc32cd4a2dfefe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 10V, Negative-QTOFsplash10-03di-0002900000-322cae85ce921a9ef9e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 20V, Negative-QTOFsplash10-03di-0004900000-d25be97b0cfa1b9bed792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 40V, Negative-QTOFsplash10-000t-2019000000-3b119d03e184f575cdc42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 10V, Positive-QTOFsplash10-03xr-2219400000-9acb072e76ff1b8f2e482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 20V, Positive-QTOFsplash10-0159-7259000000-a7f52c0e28b61ef2a3ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 40V, Positive-QTOFsplash10-0536-9320000000-8a54eac3182f86b7095b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 20V, Negative-QTOFsplash10-03di-0001900000-fe3ab0b12c2d51198ed02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmasterol 40V, Negative-QTOFsplash10-0a4i-1001900000-43dce6fa5af31f5d79582021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.15 (0.24-55.00) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
BloodDetected and Quantified5.573 +/- 0.727 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00003 +/- 0.00003 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified46.8 +/- 1.2 uMAdult (>18 years old)BothPhytosterolemia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001936
KNApSAcK IDC00023774
Chemspider ID4444352
KEGG Compound IDC05442
BioCyc IDCPD-4162
BiGG IDNot Available
Wikipedia LinkStigmasterol
METLIN ID168
PubChem Compound5280794
PDB IDNot Available
ChEBI ID28824
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGeng, Jianguo; Gu, Wenying; Wang, Xiaobao; Gu, Wenying. Method for extraction stigmasterol from mixed sterol of plant. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:12829005 ]
  2. 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 ]
  3. 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. [PubMed:15893885 ]
  4. 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. [PubMed:15573599 ]
  5. 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. [PubMed:15844941 ]
  6. 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. [PubMed:15522137 ]
  7. 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. [PubMed:6768564 ]
  8. 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. [PubMed:15638998 ]
  9. 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. [PubMed:1111441 ]

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805