Showing metabocard for (S)-2,3-Epoxysqualene (BMDB0001188)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:17 UTC
Update Date2020-04-22 15:07:03 UTC
BMDB IDBMDB0001188
Secondary Accession Numbers
  • BMDB01188
Metabolite Identification
Common Name(S)-2,3-Epoxysqualene
Description(3S)-2,3-epoxy-2,3-dihydrosqualene, also known as (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units (3S)-2,3-epoxy-2,3-dihydrosqualene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-Squalene-2,3-epoxideHMDB
Squalene 2,3-epoxideHMDB
Squalene 2,3-oxideHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(3S)-2,2-dimethyl-3-[(3Z,7E,11Z,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
Traditional Name(3S)-2,2-dimethyl-3-[(3Z,7E,11Z,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
CAS Registry Number9029-62-3
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C/CC\C=C(/C)CC\C=C(\C)CC[C@]1([H])OC1(C)C
InChI Identifier
InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15-,26-16+,27-20+,28-21-/t29-/m0/s1
InChI KeyQYIMSPSDBYKPPY-CBMIWKPVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.58ALOGPS
logP9.44ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity143.46 m³·mol⁻¹ChemAxon
Polarizability55.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rf-3696400000-dd04dae2363e5ff874a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0424900000-45b1f62177f69536d624View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-6549200000-1fc45aff6d7829383aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dr-7492000000-8f3b1e8848877c4f3099View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-180630471fad3d5ffc90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2000900000-727a64bd610baa87c554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9205300000-2ffaa263ecaf2ba728cfView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0059621
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022476
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01054
BioCyc IDEPOXYSQUALENE
BiGG ID36708
Wikipedia LinkNot Available
METLIN ID3530
PubChem Compound53477723
PDB IDNot Available
ChEBI ID15441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol synthase
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus. Through the production of lanosterol may regulate lens protein aggregation and increase transparency.
Gene Name:
LSS
Uniprot ID:
P84466
Molecular weight:
83184.0