fecosteryl oleate (YMDB00544)

Identification

YMDB ID

YMDB00544

Name

fecosteryl oleate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

fecosteryl 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. fecosteryl oleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Fecosteryl oleic acid

CAS number

Not Available

Weight

Average: 663.1103
Monoisotopic: 662.60018174

InChI Key

HMMVQRABXKLEQV-ASZKISFMSA-N

InChI

InChI=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/h15-16,35,37-39,41-42H,4,8-14,17-34H2,1-3,5-7H3/b16-15-/t37-,38+,39+,41-,42+,45+,46-/m1/s1

IUPAC Name

(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-1(10)-en-5-yl (9Z)-octadec-9-enoate

Traditional IUPAC Name

fecosteryl oleate

Chemical Formula

C₄₆H₇₈O₂

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3=C(CC[C@@]2([H])C1)[C@]1([H])CC[C@]([H])([C@H](C)CCC(=C)C(C)C)[C@@]1(C)CC3

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
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

fecosterol ester (CHEBI:52379 )
Ergosterols and C24-methyl derivatives (LMST01031012 )

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	3.0e-05 g/L	ALOGPS
logP	10.55	ALOGPS
logP	14.46	ChemAxon
logS	-7.4	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	22	ChemAxon
Refractivity	208.59 m³·mol⁻¹	ChemAxon
Polarizability	87.69 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

24-methylidene-5alpha-cholest-8-en-3beta-ol + oleoyl-CoA ↔ fecosteryl 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	splash10-03yi-2154029000-00b45f78256343176e78	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ls-6398031000-13714a8bb6b9a02de133	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01c9-9378040000-a3560df402ceb4a22a18	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0024009000-ef41f9d323682620518b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ot-0059103000-342f362baf85bb41b0a7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001m-3029000000-233328b2f66c34f48bcc	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	52379
HMDB ID	Not Available
Pubchem Compound ID	25271607
Kegg ID	Not Available
ChemSpider ID	23107002
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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:0xaf7b91c0>

Enzymes

Reactions