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Record Information
Version1.0
Creation date2011-09-21 00:14:37 UTC
Update date2020-09-17 15:38:50 UTC
Primary IDFDB022476
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number9029-62-3
Structure
Thumb
Synonyms
SynonymSource
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O
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
InChI IdentifierInChI=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
Isomeric SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rf-3696400000-dd04dae2363e5ff874a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0424900000-7fc557d70c5c9e3da792JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4859200000-154cc236135feb13b7feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7493000000-f50f29f61b0b15da33f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-51b63741b5f02135d106JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2000900000-5a6929cb0f28227226e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105300000-2fc6b31bfdb56acb80f9JSpectraViewer
ChemSpider ID30776536
ChEMBL IDNot Available
KEGG Compound IDC01054
Pubchem Compound ID53477723
Pubchem Substance IDNot Available
ChEBI ID15441
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01188
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36708
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Putative uncharacterized protein DKFZp686B0215DKFZp686B0215Q5HYI4
Lanosterol synthaseLSSP48449
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference