lanosteryl oleate (YMDB00546)

Identification

YMDB ID

YMDB00546

Name

lanosteryl oleate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

lanosteryl oleate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. lanosteryl oleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Lanosta-8,24-dien-3β-yl (9Z)-octadec-9-enoate
Lanosta-8,24-dien-3β-yl (9Z)-octadec-9-enoic acid
Lanosteryl oleic acid

CAS number

Not Available

Weight

Average: 691.1635
Monoisotopic: 690.631481868

InChI Key

DKYFEOWQCCNWLB-GYZZQDEESA-N

InChI

InChI=1S/C48H82O2/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-28-44(49)50-43-33-34-46(7)40-32-36-47(8)39(38(4)27-25-26-37(2)3)31-35-48(47,9)41(40)29-30-42(46)45(43,5)6/h17-18,26,38-39,42-43H,10-16,19-25,27-36H2,1-9H3/b18-17-/t38-,39-,42+,43+,46-,47-,48+/m1/s1

IUPAC Name

(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-yl (9Z)-octadec-9-enoate

Traditional IUPAC Name

lanosteryl oleate

Chemical Formula

C₄₈H₈₂O₂

SMILES

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid ester
14-alpha-methylsteroid
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

lanosteryl ester (CHEBI:52382 )
Steryl esters (LMST01020032 )

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	1.9e-05 g/L	ALOGPS
logP	11.04	ALOGPS
logP	15.15	ChemAxon
logS	-7.6	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	218.45 m³·mol⁻¹	ChemAxon
Polarizability	92.29 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

oleoyl-CoA + Lanosterin ↔ Coenzyme A + lanosteryl oleate

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	splash10-00kf-0140409000-1088da55ff41d3a84b64	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06fr-3393714000-51c71e430575dd62bec7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-4259124000-64be68215e431f63c577	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0020509000-900c74ea58c66d174614	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0040903000-c2972d753b7e9e133ddc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-3022900000-73df0c3ceab378e5d1e3	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	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
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	52382
HMDB ID	Not Available
Pubchem Compound ID	25271609
Kegg ID	Not Available
ChemSpider ID	23107005
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:0xb1987a7c>

Enzymes

Reactions