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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:04:44 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
Thumb
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
DescriptionThis compound 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
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular 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
Polarizability55.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot Available
Displaying entries 1 - 5 of 23 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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

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