zymosteryl palmitoleate (YMDB00554)

Identification

YMDB ID

YMDB00554

Name

zymosteryl palmitoleate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

zymosteryl palmitoleate belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. zymosteryl palmitoleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Zymosteryl palmitoleic acid

CAS number

Not Available

Weight

Average: 621.0306
Monoisotopic: 620.553231548

InChI Key

RKBOCYGCMVZAEZ-MMBTXPDKSA-N

InChI

InChI=1S/C43H72O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,21,34-36,38-39H,7-11,14-20,22-32H2,1-6H3/b13-12-/t34-,35+,36+,38-,39+,42+,43-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

zymosteryl palmitoleate

Chemical Formula

C₄₃H₇₂O₂

SMILES

CCCCCC\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@@]1(C)CC3

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholestane steroids

Alternative Parents

Substituents

Cholestane-skeleton
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

zymosterol ester (CHEBI:52385 )
Steryl esters (LMST01020035 )

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	10.54	ALOGPS
logP	13.22	ChemAxon
logS	-7.5	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	19	ChemAxon
Refractivity	195.91 m³·mol⁻¹	ChemAxon
Polarizability	82.56 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

zymosterol ↔ zymosteryl palmitoleate + 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	splash10-00dr-1256049000-2d9c65af4a1a00ce7e3b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-4659040000-7271a4e05ccffa452d86	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07do-4819240000-d24fd5679fff49f331d3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0024009000-10728694041bebcf1a86	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-0049103000-7867c03f0d278193203f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-2029000000-c58a083015235ec11379	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	52385
HMDB ID	Not Available
Pubchem Compound ID	25271594
Kegg ID	Not Available
ChemSpider ID	23107008
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:0xa66ae1a8>

Enzymes

Reactions