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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001188
Secondary Accession Numbers
  • HMDB0059621
  • HMDB01188
  • HMDB59621
Metabolite Identification
Common Name(S)-2,3-Epoxysqualene
Description(S)-2,3-Epoxysqualene, also known as 2,3-oxidosqualene or (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, (S)-2,3-epoxysqualene is considered to be an isoprenoid lipid molecule. (S)-2,3-Epoxysqualene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of terpenoid. It is a substrate for squalene monooxygenase and lanosterol synthase.
Structure
Data?1583421638
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
(3S)-2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaen-1-yl]oxiraneHMDB
(S)-2,3-EpoxysqualeneHMDB
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.82831661259
DarkChem[M-H]-200.43531661259
AllCCS[M+H]+222.26232859911
AllCCS[M-H]-208.06332859911
DeepCCS[M+H]+221.30730932474
DeepCCS[M-H]-218.94930932474
DeepCCS[M-2H]-251.83630932474
DeepCCS[M+Na]+227.40130932474
AllCCS[M+H]+222.332859911
AllCCS[M+H-H2O]+220.232859911
AllCCS[M+NH4]+224.132859911
AllCCS[M+Na]+224.732859911
AllCCS[M-H]-208.132859911
AllCCS[M+Na-2H]-210.732859911
AllCCS[M+HCOO]-213.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-2,3-EpoxysqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C3057.7Standard polar33892256
(S)-2,3-EpoxysqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C2838.1Standard non polar33892256
(S)-2,3-EpoxysqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C2987.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2,3-Epoxysqualene GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rf-3696400000-dd04dae2363e5ff874a82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2,3-Epoxysqualene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Positive-QTOFsplash10-004i-0424900000-7fc557d70c5c9e3da7922016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Positive-QTOFsplash10-014i-4859200000-154cc236135feb13b7fe2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Positive-QTOFsplash10-0gb9-7493000000-f50f29f61b0b15da33f72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Negative-QTOFsplash10-004i-0000900000-51b63741b5f02135d1062016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Negative-QTOFsplash10-004i-2000900000-5a6929cb0f28227226e92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Negative-QTOFsplash10-0a4i-9105300000-2fc6b31bfdb56acb80f92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Negative-QTOFsplash10-004i-1101900000-db9a88388cd111945a572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Negative-QTOFsplash10-052u-2339100000-6f4e24f11b72c0cb1c242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Positive-QTOFsplash10-05rr-4545900000-9f67cba78f15989d34a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Positive-QTOFsplash10-066r-5609300000-19d2e2da63dd111fdd582021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Positive-QTOFsplash10-053u-9603000000-d795105f1da47d79c7dd2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB022476
KNApSAcK IDC00007282
Chemspider ID4573579
KEGG Compound IDC01054
BioCyc IDEPOXYSQUALENE
BiGG IDNot Available
Wikipedia Link2,3-Oxidosqualene
METLIN IDNot Available
PubChem Compound5459811
PDB IDNot Available
ChEBI ID15441
Food Biomarker OntologyNot Available
VMH IDSSQ23EPX
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Kimura M, Kushiro T, Shibuya M, Ebizuka Y, Abe I: Protostadienol synthase from Aspergillus fumigatus: functional conversion into lanosterol synthase. Biochem Biophys Res Commun. 2010 Jan 1;391(1):899-902. doi: 10.1016/j.bbrc.2009.11.160. Epub 2009 Nov 29. [PubMed:19951700 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:
SQLE
Uniprot ID:
Q14534
Molecular weight:
63922.505
Reactions
Squalene + Reduced acceptor + Oxygen → (S)-2,3-Epoxysqualene + Acceptor + Waterdetails
Squalene + Oxygen + NADPH + Hydrogen Ion → (S)-2,3-Epoxysqualene + NADP + Waterdetails
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
Reactions
(S)-2,3-Epoxysqualene → Lanosteroldetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DKFZp686B0215
Uniprot ID:
Q5HYI4
Molecular weight:
63793.4