Record Information
Version1.0
Creation date2010-04-08 22:05:10 UTC
Update date2019-11-27 17:05:42 UTC
Primary IDFDB001936
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameStigmasterol
DescriptionStigmasterol, also known as phytosterol or poriferasterol, 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. Thus, stigmasterol is considered to be a sterol lipid molecule. Stigmasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number83-48-7
Structure
Thumb
Synonyms
SynonymSource
(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
(24AFH)-stigmasta-5,22t-dien-3b-olHMDB
(24S)-5,22-Stigmastadien-3b-olHMDB
(24X)-Ethylcholesta-5,22-dien-3b-olHMDB
(24XH)-Stigmasta-5,22t-dien-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
24AFH-stigmasta-5,22t-dien-3b-olHMDB
24X-24-Ethylcholest-5,22-dien-3b-olHMDB
rac-(24XH)-Stigmasta-5,22t-dien-3b-olHMDB
Stigmasta-5,22-dien-3-b-olHMDB
Stigmasta-5,22-dien-3-beta-olHMDB
Stigmasta-5,22t-dien-3b-olHMDB
StigmasterinHMDB
(22E)-Stigmasta-5,22-dien-3-olbiospider
(22E)-Stigmasta-5,22-dien-3beta-olbiospider
(24S)-24-Ethylcholesta-5,22-dien-3beta-olbiospider
(24S)-5,22-Stigmastadien-3β-olbiospider
(24S)-5,22-stigmastadien-3b-olbiospider
(24S)-5,22-Stigmastadien-3beta-olbiospider
(24S)-Stigmast-5,22-dien-3beta-olbiospider
β-Stigmasterolbiospider
D5-Stigmasterolbiospider
Delta5-Stigmasterolbiospider
Delta5,22-Stigmastadien-3beta-olbiospider
Serposteroldb_source
Stigmasta-5,22-dien-3-ol, (3β,22E)-biospider
Stigmasta-5,22-dien-3-ol, (3β)-biospider
Stigmasta-5,22-dien-3-ol, (3beta,22E)- (9CI)biospider
Stigmasta-5,22-dien-3-ol, (3beta)-biospider
Stigmasta-5,22-dien-3β-olbiospider
Stigmasta-5,22-dien-3beta-ol (8CI)biospider
Stigmasteroldb_source
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H48O
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
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
Isomeric 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
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
Classification
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 84.40%; H 11.72%; O 3.88%DFC
Melting PointMp 170°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -57 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae49View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c313295View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda7530View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e450View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3941000000-4b20188a87c1dadeae49View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9720000000-02211a4df6ec5c313295View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-7941000000-7983b2cb8a74cfda7530View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9731000000-168578ccead65322e450View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1109000000-be897608aaeab74e5d13View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0avl-2102900000-564b610342ad160ee822View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0000900000-f7738a3fcdee344f82c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-07cs-9400200000-959314bea26c5acd8301View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a59-7900000000-ce066e558ecbe29afea8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0a4i-3941000000-f854893a9352ff766734View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a59-9720000000-5a3d902c3cd2af078da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-053r-7941000000-6c5c63e8c487f86b353bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a59-9731000000-32a70fa14fd448314caaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2019500000-3495ed3a1955cc77528aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9128100000-3c3b91bb2d698a88f9dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8197000000-a80e8fcc32cd4a2dfefeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-322cae85ce921a9ef9e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-d25be97b0cfa1b9bed79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-2019000000-3b119d03e184f575cdc4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a59-8920000000-c7d02c3957677fae28beView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05442
Pubchem Compound ID5280794
Pubchem Substance IDNot Available
ChEBI ID28824
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00937
CRC / DFC (Dictionary of Food Compounds) IDHKT95-L:CBG86-I
EAFUS IDNot Available
Dr. Duke IDSTIGMASTEROL
BIGG IDNot Available
KNApSAcK IDC00023774
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDStigmasterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
anti ophidicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
artemicideDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
estrogenicDUKE
hypocholesterolemicDUKE
ovulantDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.