(S)-2,3-epoxysqualene (YMDB00727)

Identification
YMDB IDYMDB00727
Name(S)-2,3-epoxysqualene
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(3S)-2,3-epoxy-2,3-dihydrosqualene, also known as (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units (3S)-2,3-epoxy-2,3-dihydrosqualene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-2,3-Epoxysqualene
  • (S)-Squalene-2,3-epoxide
  • Squalene 2,3-epoxide
  • Squalene 2,3-oxide
CAS number9029-62-3
WeightAverage: 426.7174
Monoisotopic: 426.386166222
InChI KeyQYIMSPSDBYKPPY-RSKUXYSASA-N
InChIInChI=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
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 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
Chemical FormulaC30H50O
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
squalene + oxygen + NADPH → (S)-2,3-epoxysqualene + water + NADP
(S)-2,3-epoxysqualene → Lanosterin
KEGG Reactions
(S)-2,3-epoxysqualene → Lanosterin
NADH + squalene + hydron + oxygen → NAD + (S)-2,3-epoxysqualene + water
squalene + NADPH + hydron + oxygen → NADP + (S)-2,3-epoxysqualene + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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-0424900000-45b1f62177f69536d624JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-6549200000-1fc45aff6d7829383aceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dr-7492000000-8f3b1e8848877c4f3099JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-180630471fad3d5ffc90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2000900000-727a64bd610baa87c554JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9205300000-2ffaa263ecaf2ba728cfJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Lamb, D. C., Kelly, D. E., Manning, N. J., Kaderbhai, M. A., Kelly, S. L. (1999). "Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction." FEBS Lett 462:283-288.10622712
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15441
HMDB IDHMDB01188
Pubchem Compound ID439382
Kegg IDC01054
ChemSpider ID24823131
FOODB IDFDB022476
Wikipedia IDNot Available
BioCyc IDEPOXYSQUALENE

Enzymes

Protein 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:
ERG1
Uniprot ID:
P32476
Molecular weight:
55125.39844
Reactions
Squalene + AH(2) + O(2) → (S)-squalene-2,3-epoxide + A + H(2)O.
Protein 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:
ERG7
Uniprot ID:
P38604
Molecular weight:
83460.70313
Reactions
(S)-2,3-epoxysqualene → lanosterol.
Protein Details
3. NADPH--cytochrome P450 reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5
Gene Name:
NCP1
Uniprot ID:
P16603
Molecular weight:
76771.10156
Reactions
NADPH + n oxidized hemoprotein → NADP(+) + n reduced hemoprotein.