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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:47 UTC
HMDB IDHMDB0001188
Secondary Accession Numbers
  • HMDB01188
Metabolite Identification
Common Name(S)-2,3-Epoxysqualene
Description(S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Squalene monooxygenase and Lanosterol synthase.
Structure
Data?1563860687
Synonyms
ValueSource
(3S)-2,3-Dihydro-2,3-epoxysqualeneChEBI
(3S)-2,3-Epoxy-2,3-dihydrosqualeneChEBI
(S)-2,3-Dihydro-2,3-epoxysqualeneChEBI
(S)-2,3-Epoxy-2,3-dihydrosqualeneChEBI
(S)-2,3-OxidosqualeneChEBI
(S)-Squalene-2,3-epoxideChEBI
2,3-EDSQChEBI
2,3-EpoxisqualeneChEBI
2,3-OxidosqualeneChEBI
OxidosqualeneChEBI
Squalene 2,3-epoxideChEBI
Squalene 2,3-oxideChEBI
2,3-Epoxy-2,3-dihydrosqualeneHMDB
2,3-Oxidosqualene, (R)-isomerHMDB
2,3-Oxidosqualene, (R-(all-e))-isomerHMDB
2,3-Oxidosqualene, (all-e)-(+-)-isomerHMDB
Squalene monohydroperoxideHMDB
Squalene-2,3-epoxideHMDB
(3S)-OxidosqualeneHMDB
2,3-Oxidosqualene, (S-(all-e))-isomerHMDB
Squalene-2,3-oxideHMDB
2,3-Oxidosqualene, (S)-isomerHMDB
Squslene oxideHMDB
Squalene peroxideHMDB
(3S)-2,3-EpoxysqualeneHMDB
(3S)-2,3-OxidosqualeneHMDB
(3S)-Squalene-2,3-epoxideHMDB
(S)-Squalene 2,3-epoxideHMDB
2,3(S)-OxidosqualeneHMDB
3(S)-OxidosqualeneHMDB
Squalene 2,3(S)-oxideHMDB
(3R,S)-OxidosqualeneHMDB
(R,S)-Squalene 2,3-epoxideHMDB
(RS)-2,3-Epoxy-2,3-dihydrosqualeneHMDB
(±)-2,3-epoxysqualeneHMDB
(±)-squalene oxideHMDB
2,3-EpoxysqualeneHMDB
Squalene epoxideHMDB
Squalene oxideHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
Traditional Namesqualene 2,3-oxide
CAS Registry Number54910-48-4
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(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-RSKUXYSASA-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 Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00042 g/LALOGPS
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
Polarizability57.02 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rf-3696400000-dd04dae2363e5ff874a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0424900000-7fc557d70c5c9e3da792JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4859200000-154cc236135feb13b7feJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7493000000-f50f29f61b0b15da33f7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-51b63741b5f02135d106JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2000900000-5a6929cb0f28227226e9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105300000-2fc6b31bfdb56acb80f9JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007282
Chemspider IDNot Available
KEGG Compound IDC01054
BioCyc IDEPOXYSQUALENE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459811
PDB IDNot Available
ChEBI ID15441
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
Gene Name:
LSS
Uniprot ID:
P48449
Molecular weight:
83308.065
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DKFZp686B0215
Uniprot ID:
Q5HYI4
Molecular weight:
63793.4