You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00550
Nameepisteryl palmitoleate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionepisteryl palmitoleate 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 palmitoleate 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-3-yl 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
  • Episterol palmitoleate
  • Episterol palmitoleic acid
  • Episteryl palmitoleic acid
CAS numberNot Available
WeightAverage: 635.0572
Monoisotopic: 634.568881612
InChI KeySYZHHZICOBPDNN-ADJCQIKLSA-N
InChIInChI=1S/C44H74O2/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-42(45)46-37-28-30-43(6)36(32-37)24-25-38-40-27-26-39(44(40,7)31-29-41(38)43)35(5)23-22-34(4)33(2)3/h13-14,25,33,35-37,39-41H,4,8-12,15-24,26-32H2,1-3,5-7H3/b14-13-/t35-,36+,37+,39-,40+,41+,43+,44-/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)-hexadec-9-enoate
Traditional IUPAC Nameepisteryl palmitoleate
Chemical FormulaC44H74O2
SMILESCCCCCC\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 Solubility2.6e-05 g/LALOGPS
logP10.7ALOGPS
logP13.61ChemAxon
logS-7.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity199.65 m³·mol⁻¹ChemAxon
Polarizability83.55 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
episterolepisteryl palmitoleate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2255049000-1d7da8d059202c82b82eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-8469050000-5d5de97b714fc3f82f08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015m-9827130000-d37e1206549228a9b022JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0024009000-a4f312a335e6d4ed537cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0049103000-6881922d2f37572de867JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001m-3029000000-913084052269c3ec9f48JSpectraViewer
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 ID52376
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider ID23106999
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.