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Lanosterin (YMDB00262)

Identification
YMDB IDYMDB00262
NameLanosterin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionLanosterin, also known as botalan base 138 or lanosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, lanosterin is considered to be a sterol lipid molecule. Lanosterin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (3 beta)-Lanosta-8,24-dien-3-ol
  • (3alpha)-4,4,14-trimethyl-Cholesta-8,24-dien-3-ol
  • (3beta,5alpha)-4,4,14-trimethyl-Cholesta-8,24-dien-3-ol
  • (3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol
  • (3beta)-Lanosta-8,24-dien-3-ol
  • 4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol
  • Lanosta-8,24-dien-3-ol
  • Lanosta-8,24-dien-3-ol, (3.beta.)-
  • Lanosta-8,24-dien-3-ol, (3beta)-
  • Lanosta-8,24-dien-3.beta.-ol
  • Lanosta-8,24-dien-3beta-ol
  • Lanosta-8,24-dienol
  • Lanosterin
  • Lanosterol
  • Lanster
  • (3b)-Lanosta-8,24-dien-3-ol
  • (3β)-Lanosta-8,24-dien-3-ol
  • (3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-ol
  • (3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-ol
  • 4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-ol
  • 4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-ol
  • Botalan base 138
  • 4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol
  • Kryptosterol
  • 3beta-Hydroxy-lansota-8,24-dien-21-oic acid
  • 3beta-Hydroxylanosta-8,24-diene
  • 3β-Hydroxy-lansota-8,24-dien-21-oic acid
  • 3β-Hydroxylanosta-8,24-diene
  • 4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-ol
  • 4,4,14α-Trimethylcholesta-8,24-dien-3β-ol
  • 5alpha-Lanosta-8,24-dien-3beta-ol
  • 5α-Lanosta-8,24-dien-3β-ol
  • Lanosta-8,24-dien-3β-ol
  • Lanostadien-3beta-ol
  • Lanostadien-3β-ol
CAS number79-63-0
WeightAverage: 426.7174
Monoisotopic: 426.386166222
InChI KeyCAHGCLMLTWQZNJ-BQNIITSRSA-N
InChIInChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Chemical FormulaC30H50O
SMILES[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C([H])([H])C([H])([H])[C@@]2([H])C1(C([H])([H])[H])C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@@]1(C([H])([H])[H])C([H])([H])C3([H])[H])C([H])([H])[H]
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
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point140.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP7.72ALOGPS
logP7.71ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.54 m³·mol⁻¹ChemAxon
Polarizability55.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • 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
(S)-2,3-epoxysqualene → Lanosterin
Lanosterin + NADPH ↔ 24,25-dihydrolanosterol + NADP
Lanosterin + oxygen + NADPH → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + water
KEGG Reactions
oleoyl-CoA + Lanosterin ↔ Coenzyme A + lanosteryl oleate
Lanosterin ↔ Coenzyme A + lanosteryl palmitoleate
oxygen + NADH + hydron + Lanosterin → water + Formic acid + NAD + 4,4-Dimethylcholesta-8,14,24-trienol
oxygen + hydron + NADPH + Lanosterin → NADP + water + Formic acid + 4,4-Dimethylcholesta-8,14,24-trienol
(S)-2,3-epoxysqualene → Lanosterin
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-2953300000-ae1832f19369485ff53cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aou-9820200000-573525b346ad3c9eef59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2910000000-c67a1f122f33698a14f6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0a6r-0110900000-5e42e1f2d9ad534c003cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0a4i-0230900000-10f58fa6e118cd7c5997JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-1791800000-178153ad92eececb33c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0a4i-2980300000-6ce95c7f8b15b35475afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-0a4j-2950100000-48f86ff7a22c596aa44dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0592-3940000000-c35d0cb6a2e4e291e8f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0592-3920000000-d717fdd3322a881bef99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-0592-4910000000-4c6d07e3a8e48ae88580JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0a4j-5900000000-4c8b72037dbeae9a46d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-067m-8900000000-522b8688d50362297c41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 62V, positivesplash10-0aou-9700000000-70d433827c1a6dab0c41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-05ox-9500000000-5b122dea636d3e3b5916JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, positivesplash10-05r3-9500000000-0c1c5cbd994f8406f30eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 111V, positivesplash10-05r3-9600000000-5cb8ae11d071fa19f206JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0ktf-0392000000-03cda521ce6e102d92e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-059j-2900000000-8086693fb040e5ed7501JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0a4i-4900000000-c58ff2dc28c6ba639997JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-01vk-0900000000-805937445cceda0cd70aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0aor-0900000000-22d304b445b737121aa7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-2cfcf7ce4b5b21140eaeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-2139500000-9a25961000db9796d6daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4259100000-9f7f26265abec4122e35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-77a57cecc2069bee1926JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-5b0f06bf8120e780e30cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-421e305d47b29da427d2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd687JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • Wilcox, L. J., Balderes, D. A., Wharton, B., Tinkelenberg, A. H., Rao, G., Sturley, S. L. (2002). "Transcriptional profiling identifies two members of the ATP-binding cassette transporter superfamily required for sterol uptake in yeast." J Biol Chem 277:32466-32472.12077145
  • 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
  • Zweytick, D., Leitner, E., Kohlwein, S. D., Yu, C., Rothblatt, J., Daum, G. (2000). "Contribution of Are1p and Are2p to steryl ester synthesis in the yeast Saccharomyces cerevisiae." Eur J Biochem 267:1075-1082.10672016
Synthesis Reference:Maienthal, Millard; Franklin, Philip J. Preparation of lanosterol from bromolanosterol. Journal of Organic Chemistry (1955), 20 1627-30.
External Links:
ResourceLink
CHEBI ID16521
HMDB IDHMDB01251
Pubchem Compound ID246983
Kegg IDC01724
ChemSpider ID23253432
FOODB IDFDB013802
WikipediaLanosterol
BioCyc IDLANOSTEROL

Enzymes

Protein Details
1. Lanosterol 14-alpha demethylase
General function:
Involved in iron ion binding
Specific function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Gene Name:
ERG11
Uniprot ID:
P10614
Molecular weight:
60719.80078
Reactions
Obtusifoliol + 3 O(2) + 3 NADPH → 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.
Protein Details
2. Sterol O-acyltransferase 1
General function:
Involved in O-acyltransferase activity
Specific function:
Acyl-CoA + cholesterol = CoA + cholesterol ester
Gene Name:
ARE1
Uniprot ID:
P25628
Molecular weight:
71612.5
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
Protein Details
3. 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.

Transporters

Protein Details
1. ATP-dependent permease AUS1
General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
AUS1
Uniprot ID:
Q08409
Molecular weight:
157750.0
Protein Details
2. ATP-dependent permease PDR11
General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
PDR11
Uniprot ID:
P40550
Molecular weight:
160536.0