Showing metabocard for Stigmasterol (BMDB0062199)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-29 22:18:12 UTC
Update Date2020-05-05 18:40:40 UTC
BMDB IDBMDB0062199
Secondary Accession Numbers
  • BMDB62199
Metabolite Identification
Common 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.
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 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(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[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
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Liver
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000937
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available