episterol (YMDB00540)

Identification
YMDB IDYMDB00540
Nameepisterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionepisterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, episterol is considered to be a sterol lipid molecule. episterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (3beta,5alpha)-ergosta-7,24(28)-dien-3-ol
  • ergosta-7,24(28)-dien-3-ol
  • (3b,5a)-Ergosta-7,24(28)-dien-3-ol
  • (3Β,5α)-ergosta-7,24(28)-dien-3-ol
  • Episterol, (3beta)-isomer
  • 24-Methyl-5alpha-cholesta-7,24(28)-dien-3beta-ol
  • 24-Methyl-5α-cholesta-7,24(28)-dien-3β-ol
  • 24-Methylene-5alpha-cholest-7-en-3beta-ol
  • 24-Methylene-5α-cholest-7-en-3β-ol
  • 24-Methylenecholesta-7,24(28)-dien-3beta-ol
  • 24-Methylenecholesta-7,24(28)-dien-3β-ol
  • 5alpha-Ergosta-7,24(28)-dien-3beta-ol
  • 5α-Ergosta-7,24(28)-dien-3β-ol
  • Episterin
  • Episterol
  • delta7,24(28)-Ergostadienol
  • Δ7,24(28)-Ergostadienol
CAS number474-68-0
WeightAverage: 398.6642
Monoisotopic: 398.354866094
InChI KeyBTCAEOLDEYPGGE-JVAZTMFWSA-N
InChIInChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h10,18,20-22,24-26,29H,3,7-9,11-17H2,1-2,4-6H3/t20-,21+,22+,24-,25+,26+,27+,28-/m1/s1
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Chemical FormulaC28H46O
SMILES[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-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 pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP7.16ALOGPS
logP7.05ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.94 m³·mol⁻¹ChemAxon
Polarizability51.53 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
24-methylidene-5alpha-cholest-8-en-3beta-ol → episterol
episterol + hydron + oxygen + Pentane → 5,7,24(28)-Ergostatrienol + water + ferricytochrome c
KEGG Reactions
episterol + oleoyl-CoA ↔ episteryl oleate + Coenzyme A
episterol ↔ episteryl palmitoleate + Coenzyme A
episterol + NADPH + hydron + oxygen → water + NADP + ergosta-5,7,24(28)-trien-3beta-ol
24-methylidene-5alpha-cholest-8-en-3beta-ol → episterol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-f4a8a4bd75686a2c4264JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-3bad18e0101e63aec08dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2019000000-89152080214a606e3f42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-1e3548d588af0130a112JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-61513522be83c13652a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0019000000-4a337e3ab572869d5978JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-6049000000-bccf170e8638d30f9658JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-6194000000-1b24202010ace7360df4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0029000000-4b2163dd09b4a7542a36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9156000000-85e4ecbe743df768234dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9500000000-11d7124be40b6765e3abJSpectraViewer
References
References:
  • 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
  • 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
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID23929
HMDB IDHMDB06847
Pubchem Compound ID47205103
Kegg IDC15777
ChemSpider ID23254214
FOODB IDFDB024116
WikipediaEpisterol
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
2. C-5 sterol desaturase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the introduction of a C-5 double bond in the B ring of ergosterol. May contribute to the regulation of ergosterol biosynthesis
Gene Name:
ERG3
Uniprot ID:
P32353
Molecular weight:
42729.89844
Reactions
Protein Details
3. C-8 sterol isomerase
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Catalyzes the reaction which results in unsaturation at C-7 in the B ring of sterols
Gene Name:
ERG2
Uniprot ID:
P32352
Molecular weight:
24895.40039
Reactions

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