ergosteryl palmitoleate (YMDB00551)

Identification
YMDB IDYMDB00551
Nameergosteryl palmitoleate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionergosteryl 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. ergosteryl palmitoleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Ergosteryl palmitoleic acid
CAS numberNot Available
WeightAverage: 633.0413
Monoisotopic: 632.553231548
InChI KeyYNMORHVGYFUEDW-CPYZXPJNSA-N
InChIInChI=1S/C44H72O2/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/h13-14,22-25,33-35,37,39-41H,8-12,15-21,26-32H2,1-7H3/b14-13-,23-22+/t34-,35+,37-,39+,40-,41-,43-,44+/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)-hexadec-9-enoate
Traditional IUPAC Nameergosteryl palmitoleate
Chemical FormulaC44H72O2
SMILESCCCCCC\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 Solubility1.0e-05 g/LALOGPS
logP10.77ALOGPS
logP13.19ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity201.84 m³·mol⁻¹ChemAxon
Polarizability82.46 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 ↔ ergosteryl palmitoleate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-4265069000-e8b7f50cfe29c6e4f254JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001a-8469050000-049dfe93c16483856245JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9737130000-da69318f0a0986411ad1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0024009000-b91264b425139c3c1989JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0049103000-dd629e60ac61b0606c89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-3029000000-63514fd88cd5546f2b5aJSpectraViewer
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 ID52378
HMDB IDNot Available
Pubchem Compound ID25271606
Kegg IDNot Available
ChemSpider ID23107001
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Sterol O-acyltransferase 2
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.
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.