Cer 18:0;3/22:0;0 (YMDB01105)

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Identification

YMDB ID

YMDB01105

Name

Cer 18:0;3/22:0;0

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Cer 18:0;3/22:0;0 is a ceramide. Ceramides are composed of a sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells. Caramides are known to promote transport of secretory vesicles from the ER to the Golgi apparatus. Sphingolipids like ceramide play import roles in lipid rafts which in yeast are responsible for delivering and sorting membrane bound proteins. Lipid rafts also play roles in membrane fusion during mating.[PMID: 16730802]

There are three major pathways of ceramide generation. The sphingomyelinase pathway uses an enzyme to breakdown IPC, MIPC and M(IP)2C in the cell membrane and release ceramide. The de novo pathway creates ceramide from less complex molecules. Ceramide generation can also occur through breakdown of complex sphingolipids that are ultimately broken down into sphingosine, which is then reused by reacylation to form ceramide. This latter pathway is termed the Salvage pathway.[Wikipedia, PMID: 16730802]Lipid identified in the yeast S. cerevisiae

Structure

MOL SDF PDB SMILES InChI

Synonyms

N-(Docosanoyl)-4-hydroxysphinganine
N-(Docosanoyl)-4R-hydroxysphinganine
N-(Docosanoyl)-phytoceramide
N-Behenoyl-4-hydroxysphinganine
N-Behenoylphytoceramide
N-Behenoylphytosphingosine
N-Docosanoylphytoceramide
N-Docosanoylphytosphingosine
PHC-b 18:0/22:0
Cer(t18:0/22:0)

CAS number

Not Available

Weight

Average: 640.0754
Monoisotopic: 639.616560085

InChI Key

CIMNZQFRNXDRER-HIERITDVSA-N

InChI

InChI=1S/C40H81NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-39(44)41-37(36-42)40(45)38(43)34-32-30-28-26-24-16-14-12-10-8-6-4-2/h37-38,40,42-43,45H,3-36H2,1-2H3,(H,41,44)/t37-,38+,40-/m0/s1

IUPAC Name

N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]docosanamide

Traditional IUPAC Name

N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]docosanamide

Chemical Formula

C₄₀H₈₁NO₄

SMILES

[H][C@@](O)([C@H](O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCCCCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Phytoceramides

Alternative Parents

Substituents

N-acyl-4-hydroxysphinganine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Polyol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phytoceramide (CHEBI:67024 )
N-acyl-4-hydroxysphinganines (phytoceramides) (LMSP02030008 )

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	5.7e-05 g/L	ALOGPS
logP	9.66	ALOGPS
logP	12.66	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	0.029	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	37	ChemAxon
Refractivity	193.78 m³·mol⁻¹	ChemAxon
Polarizability	87.47 Å³	ChemAxon
Number of Rings	0	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

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Biosynthesis of unsaturated fatty acids (docosanoyl)

PW002408

KEGG Pathways

Not Available

SMPDB Reactions

Phytosphingosine + Docosanoyl-CoA → hydron + Coenzyme A + Cer 18:0;3/22:0;0

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xu-0015009000-7617488fca251b3bb5a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08n9-6129002000-f60821140ea792f2544d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-6796020000-22a081ae1fd13a709442	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0033109000-60ea3dc381ef3b1062f8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ac9-1049002000-4eeece4594e5328d1911	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9133000000-ec650ad6549e0e853b18	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:

Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Dickson, R. C. (2008). "Thematic review series: sphingolipids. New insights into sphingolipid metabolism and function in budding yeast." J Lipid Res 49:909-921.18296751

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	67024
HMDB ID	Not Available
Pubchem Compound ID	5322153
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xaf650b30>