ChemFOnt: Showing chemical card for N-Lignoceroylsphingosine (CFc000000665)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:07 UTC

Chemfont ID

CFc000000665

Molecule Identification

Common Name

N-Lignoceroylsphingosine

Definition

Ceramide (N-acyl sphingosine) is known as an important precursor common to the biosynthesis of glycosphingolipids and sphingomyelin. Naturally occurring ceramide is composed of various molecular species resulting from a combination of C16 and 26 fatty acids and sphingosine (sphingenine). The N-acyl chain is thought to be mainly introduced by the acylation of sphinganine, and the resultant dihydroceramide (N-acyl sphinganine) is desaturated to form ceramide. The hydrolysis of sphingolipids also yields ceramide and may further lead to the generation of sphingosine and sphingosine phosphate. Recent studies have established the existence of a sphingomyelin cycle or a sphingomyelin pathway that operates in response to various agonists and stresses. Ceramide, is thought to act as a second messenger in the intracellular signaling pathway to apoptosis, cell cycle arrest, cell differentiation, cell propagation, or induction of cytokine synthesis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C24-Ceramide	HMDB
D-erythro-1,3-Dihydroxy-2-tetracosanoylamido-trans-4-octadecene	HMDB
Lobophytamide L5	HMDB
N-Tetracosanoyl C18-sphingosine	HMDB

Chemical Formula

C₄₂H₈₃NO₃

Average Molecular Weight

650.1133

Monoisotopic Molecular Weight

649.637295527

IUPAC Name

N-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracosanimidic acid

Traditional Name

C24-ceramide

CAS Registry Number

34435-05-7

SMILES

[H]C(CCCCCCCCCCCCC)=C([H])C(O)C(CO)N=C(O)CCCCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)/b37-35+

InChI Key

ZJVVOYPTFQEGPH-MHAUTQJVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Ceramides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0000831)
Membrane (HMDB: HMDB0000831)

Source

Exogenous

Exogenous (HMDB: HMDB0000831)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000831)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.0e-05 g/L	ALOGPS
logP	10.43	ALOGPS
logP	15.24	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	6.16	ChemAxon
pKa (Strongest Basic)	3.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	203.11 m³·mol⁻¹	ChemAxon
Polarizability	89.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022272

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5789754

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Shoyama, Yukihiro; Okabe, Hikaru; Kishimoto, Yasuo; Costello, Catherine. Total synthesis of stereospecific sphingosine and ceramide. Journal of Lipid Research (1978), 19(2), 250-9.

Showing chemical card for N-Lignoceroylsphingosine (CFc000000665)

MOL for CFc000000665 (N-Lignoceroylsphingosine)

3D MOL for CFc000000665 (N-Lignoceroylsphingosine)

3D SDF for CFc000000665 (N-Lignoceroylsphingosine)

3D-SDF for CFc000000665 (N-Lignoceroylsphingosine)

PDB for CFc000000665 (N-Lignoceroylsphingosine)

3D PDB for CFc000000665 (N-Lignoceroylsphingosine)

SMILES for CFc000000665 (N-Lignoceroylsphingosine)

INCHI for CFc000000665 (N-Lignoceroylsphingosine)

Structure for CFc000000665 (N-Lignoceroylsphingosine)

3D Structure for CFc000000665 (N-Lignoceroylsphingosine)