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squalene (YMDB00769)

Identification
YMDB IDYMDB00769
Namesqualene
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSqualene, also known as spinacene or supraene, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, squalene is considered to be an isoprenoid lipid molecule. Squalene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-Tetracosahexaene
  • (E,E,E,E)-Squalene
  • 2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
  • all-trans-Squalene
  • Nikko Squalane EX
  • Spinacene
  • Squalene
  • trans-Squalene
  • Supraene
CAS number111-02-4
WeightAverage: 410.718
Monoisotopic: 410.3912516
InChI KeyYYGNTYWPHWGJRM-AAJYLUCBSA-N
InChIInChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+
IUPAC Name(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
Traditional IUPAC Namesqualene
Chemical FormulaC30H50
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(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
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-75 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP8.64ALOGPS
logP10.42ChemAxon
logS-5.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity144.62 m³·mol⁻¹ChemAxon
Polarizability56.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
FloralNot Available
SMPDB Pathways
Steroid biosynthesisPW002482 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
Farnesyl pyrophosphate + NADPH → squalene + NADP + Pyrophosphate
squalene + oxygen + NADPH → (S)-2,3-epoxysqualene + water + NADP
KEGG Reactions
NADH + squalene + hydron + oxygen → NAD + (S)-2,3-epoxysqualene + water
squalene + NADPH + hydron + oxygen → NADP + (S)-2,3-epoxysqualene + water
2-trans,6-trans-farnesyl diphosphate + NADPH + hydron → NADP + squalene + Pyrophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9600000000-280b7ccaed0215f0937cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015i-9500000000-63fc959bf17e2f6e0381JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dv-4879000000-3cfdaa630f73c021be06JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad261JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2920300000-04f33a28f9d38283345eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0323900000-9162860711ec9f8266feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02fx-2984100000-742302f14e45ce03bfddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-6495000000-83c6df474790679c40e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-4905353fab78414bcab2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-e7195906634d18bf31ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1869100000-2d7d4eb74fe0c5856cbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2844900000-f00046ef895fbe9888a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-4928000000-3dfbc6d8fc1271828c3bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-4932000000-6f14fcc4a6e8029a1652JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-45d1d2cb6b79e3bc92aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0102900000-49aa25403f6062cc3520JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-1239000000-809fbf3fc0f0117fe5d1JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0159-9610000000-aaf0145da95343082ae1JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
  • Loubbardi, A., Marcireau, C., Karst, F., Guilloton, M. (1995). "Sterol uptake induced by an impairment of pyridoxal phosphate synthesis in Saccharomyces cerevisiae: cloning and sequencing of the PDX3 gene encoding pyridoxine (pyridoxamine) phosphate oxidase." J Bacteriol 177:1817-1823.7896706
  • 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:Peng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
External Links:
ResourceLink
CHEBI ID15440
HMDB IDHMDB00256
Pubchem Compound ID1105
Kegg IDC00751
ChemSpider ID25995494
FOODB IDNot Available
WikipediaSqualene
BioCyc IDSQUALENE

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. Squalene synthase
General function:
Involved in transferase activity
Specific function:
May regulate the flux of isoprene intermediates through the sterol pathway. Squalene synthase is crucial for balancing the incorporation of farnesyl diphosphate (FPP) into sterol and nonsterol isoprene synthesis. ERG9 is also essential for cell growth in yeast
Gene Name:
ERG9
Uniprot ID:
P29704
Molecular weight:
51719.39844
Reactions
2 farnesyl diphosphate → diphosphate + presqualene diphosphate.
Presqualene diphosphate + NAD(P)H → squalene + diphosphate + NAD(P)(+).
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.