Showing Compound Card for (S)-2,3-Epoxysqualene (CDB004889)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:47:19 UTC
Updated at2020-12-07 19:11:12 UTC
CannabisDB IDCDB004889
Secondary Accession NumbersNot Available
Cannabis Compound 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 expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight426.72
Monoisotopic Molecular Weight426.3862
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:

Source:

Biological location:

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
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-2,3-Epoxysqualene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01rf-3696400000-dd04dae2363e5ff874a8Spectrum
Predicted GC-MS(S)-2,3-Epoxysqualene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0424900000-7fc557d70c5c9e3da7922016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4859200000-154cc236135feb13b7fe2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7493000000-f50f29f61b0b15da33f72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-51b63741b5f02135d1062016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2000900000-5a6929cb0f28227226e92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105300000-2fc6b31bfdb56acb80f92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1101900000-db9a88388cd111945a572021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-2339100000-6f4e24f11b72c0cb1c242021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05rr-4545900000-9f67cba78f15989d34a82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-5609300000-19d2e2da63dd111fdd582021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9603000000-d795105f1da47d79c7dd2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Squalene monooxygenaseSQLE8q24.1Q14534 details
Lanosterol synthaseLSS21q22.3P48449 details
Putative uncharacterized protein DKFZp686B0215DKFZp686B0215Q5HYI4 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001188
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Squalene monooxygenase
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
Enzyme Details
2. Lanosterol synthase
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
Enzyme Details
3. Putative uncharacterized protein DKFZp686B0215
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DKFZp686B0215
Uniprot ID:
Q5HYI4
Molecular weight:
63793.4