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Identification
YMDB IDYMDB00542
Nameergosteryl oleate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionergosteryl 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. ergosteryl oleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • Ergosteryl oleic acid
CAS numberNot Available
WeightAverage: 661.0944
Monoisotopic: 660.584531676
InChI KeyVVZNLLXLOKRQPH-NZIRWOIASA-N
InChIInChI=1S/C46H76O2/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/h15-16,24-27,35-37,39,41-43H,8-14,17-23,28-34H2,1-7H3/b16-15-,25-24+/t36-,37+,39-,41+,42-,43-,45-,46+/m0/s1
IUPAC Name(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-yl (9Z)-octadec-9-enoate
Traditional IUPAC Nameergosteryl oleate
Chemical FormulaC46H76O2
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC=C3[C@]4([H])CC[C@]([H])([C@H](C)\C=C\[C@H](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
  • Delta-5-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 Solubility8.1e-06 g/LALOGPS
logP10.93ALOGPS
logP14.08ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity211.04 m³·mol⁻¹ChemAxon
Polarizability86.25 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
ergosterol + oleoyl-CoAergosteryl oleate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0400-3154039000-1154c00a631f32d997afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00nk-6398041000-fdbcc0aec3b1c2873db4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008i-9386040000-56265571bbb57adea3e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0024009000-17165970be65d97f8f84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0059103000-0ab1c6b0a7209eb31a8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-3029000000-af51e226dda43a4c551cJSpectraViewer
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 ID52377
HMDB IDNot Available
Pubchem Compound ID25271616
Kegg IDNot Available
ChemSpider ID23107000
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in O-acyltransferase activity
Specific function:
Ensures probably most of the acyltransferase activity. Suppression of ARE2 reduces sterol ester levels to 25% of the normal value
Gene Name:
ARE2
Uniprot ID:
P53629
Molecular weight:
74022.20313
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
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.