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Identification
YMDB IDYMDB00541
Nameepisteryl oleate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionepisteryl oleate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. episteryl oleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 1-oleoyl-cholesterol
  • 18:1(9Z) Cholesterol ester
  • 3beta-Hydroxy-5-cholestene 3-oleate
  • 5-Cholesten-3b-ol 3-oleate
  • Cholest-5-en-3-beta-yl oleate
  • Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoate
  • Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acid
  • Cholest-5-en-3-ol (3beta)-, 9-octadecenoate, (Z)-
  • Cholest-5-en-3-yl (9Z)-9-octadecenoate
  • cholest-5-en-3b-yl
  • cholesterol 1-(9Z-octadecenoate
  • cholesterol 1-(9Z-octadecenoate)
  • cholesterol 1-(9Z-octadecenoic acid
  • cholesterol 1-(9Z-octadecenoic acid)
  • Cholesterol 3beta-oleate
  • Cholesterol Ester(18:1)
  • Cholesterol Ester(18:1/0:0)
  • Cholesterol Ester(18:1n9/0:0)
  • Cholesterol Ester(18:1w9/0:0)
  • Cholesterol, oleate
  • Cholesteroyl-oleate
  • Cholesteryl [9,10-3H]oleate
  • cholesteryl 1-oleoate
  • cholesteryl 1-oleoic acid
  • Cholesteryl cis-9-octadecenoate
  • Cholesteryl cis-9-octadecenoic acid
  • Cholesteryl oleate
  • Cholesteryl oleate-9,10-3H
  • Cholesteryl oleate-9,10-t2
  • Cholesteryl oleic ester
  • Cholesteryl-beta-D-glucoside
  • Cholesteryl-beta-delta-glucoside
  • Oleic acid cholesteryl ester
  • Oleoylcholesterol
  • Episteryl oleic acid
CAS numberNot Available
WeightAverage: 663.1103
Monoisotopic: 662.60018174
InChI KeyWXTXUXMQBSJEQW-PIJZSGCZSA-N
InChIInChI=1S/C46H78O2/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-44(47)48-39-30-32-45(6)38(34-39)26-27-40-42-29-28-41(46(42,7)33-31-43(40)45)37(5)25-24-36(4)35(2)3/h15-16,27,35,37-39,41-43H,4,8-14,17-26,28-34H2,1-3,5-7H3/b16-15-/t37-,38+,39+,41-,42+,43+,45+,46-/m1/s1
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl (9Z)-octadec-9-enoate
Traditional IUPAC Nameepisteryl oleate
Chemical FormulaC46H78O2
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)[C@@]([H])(CC=C3[C@]4([H])CC[C@]([H])([C@H](C)CCC(=C)C(C)C)[C@@]4(C)CC[C@]23[H])C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Delta-7-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.7e-05 g/LALOGPS
logP10.83ALOGPS
logP14.5ChemAxon
logS-7.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity208.85 m³·mol⁻¹ChemAxon
Polarizability88.48 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
episterol + oleoyl-CoAepisteryl oleate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03yi-2154029000-00b45f78256343176e78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ls-6398031000-2c12a26035d69797bffeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c9-9378040000-a3560df402ceb4a22a18JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0024009000-ef41f9d323682620518bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-0059103000-342f362baf85bb41b0a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001m-3029000000-c5433abdc31a669bc1e5JSpectraViewer
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
  • 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 ID52375
HMDB IDNot Available
Pubchem Compound ID25271605
Kegg IDNot Available
ChemSpider ID23106998
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.