ergosteryl oleate (YMDB00542)

Identification

YMDB ID

YMDB00542

Name

ergosteryl oleate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

ergosteryl 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

MOL SDF PDB SMILES InChI

Synonyms

Ergosteryl oleic acid

CAS number

Not Available

Weight

Average: 661.0944
Monoisotopic: 660.584531676

InChI Key

VVZNLLXLOKRQPH-NZIRWOIASA-N

InChI

InChI=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 Name

ergosteryl oleate

Chemical Formula

C₄₆H₇₆O₂

SMILES

CCCCCCCC\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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

ergosteryl ester (CHEBI:52377 )
Ergosterols and C24-methyl derivatives (LMST01031010 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.1e-06 g/L	ALOGPS
logP	10.93	ALOGPS
logP	14.08	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	211.04 m³·mol⁻¹	ChemAxon
Polarizability	86.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

ergosterol + oleoyl-CoA ↔ ergosteryl oleate + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0400-3154039000-1154c00a631f32d997af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00nk-6398041000-fdbcc0aec3b1c2873db4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-008i-9386040000-56265571bbb57adea3e2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0024009000-17165970be65d97f8f84	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0059103000-0ab1c6b0a7209eb31a8d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002g-3029000000-af51e226dda43a4c551c	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	52377
HMDB ID	Not Available
Pubchem Compound ID	25271616
Kegg ID	Not Available
ChemSpider ID	23107000
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not 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.

Structure for #<Compound:0xa9aa99f8>

Enzymes

Reactions

Reactions