ChemFOnt: Showing chemical card for Galactosylsphingosine (CFc000000506)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:54 UTC

Chemfont ID

CFc000000506

Molecule Identification

Common Name

Galactosylsphingosine

Definition

Galactosylsphingosine (also known as psychosine), is an intermediate in the biosynthesis of cerebrosides. It is formed from the reaction of sphingosine with UDP-galactose and then reacts with fatty acid-coenzyme A to form the cerebroside. It is a galactoside metabolite of sphingosine and can function as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactosylsphingosine are associated with globoid cell leukodystrophy (Krabbe disease), which is characterized by the dysfunction of galactosylceramidase. Galactosylsphingosine is a highly cytotoxic lipid capable of inducing cell death in a wide variety of cell types including oligodendrocytes. It is known to accumulate in the nervous system in the absence of galactosylceramidase. Galactosylsphingosine localizes to lipid rafts and perturbs membrane integrity. It also inhibits protein kinase C translocation to the plasma membrane (PMID: 24006512 ). Symptoms of Krabbe disease begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. In the first stages of the disease, the symptoms are often mistaken with those of cerebral palsy. Other symptoms include muscle weakness, spasticity, deafness, optic atrophy, optic nerve enlargement, blindness, paralysis, and difficulty when swallowing.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₄H₄₇NO₇

Average Molecular Weight

461.6325

Monoisotopic Molecular Weight

461.335252863

IUPAC Name

(3R,4S,5R,6R)-2-[(2-amino-3-hydroxyoctadec-4-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(3R,4S,5R,6R)-2-[(2-amino-3-hydroxyoctadec-4-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

2238-90-6

SMILES

[H]C(N)(COC1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C([H])(O)C=CCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/t18?,19?,20-,21+,22+,23-,24?/m1/s1

InChI Key

HHJTWTPUPVQKNA-UGJNAMAKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary alcohol
Primary amine
Alcohol
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Brain (HMDB: HMDB0000648)

Cell

Fibroblasts (HMDB: HMDB0000648)
Neuron (HMDB: HMDB0000648)

Cellular substructure

Tissue

Nervous tissue

Nervous tissue (HMDB: HMDB0000648)

Source

Exogenous

Exogenous (HMDB: HMDB0000648)

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: HMDB0000648)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.09 g/L	ALOGPS
logP	3.16	ALOGPS
logP	2.8	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	145.63 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	124.31 m³·mol⁻¹	ChemAxon
Polarizability	55.2 Å³	ChemAxon
Number of Rings	1	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

FDB022161

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

53877411

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Shapiro, David; Rachaman, Eliezer S.; Sheradsky, Tuvia. Synthetic studies on sphingolipids. X. Synthesis of psychosine. Journal of the American Chemical Society (1964), 86(20), 4472-6.

Showing chemical card for Galactosylsphingosine (CFc000000506)

MOL for CFc000000506 (Galactosylsphingosine)

3D MOL for CFc000000506 (Galactosylsphingosine)

3D SDF for CFc000000506 (Galactosylsphingosine)

3D-SDF for CFc000000506 (Galactosylsphingosine)

PDB for CFc000000506 (Galactosylsphingosine)

3D PDB for CFc000000506 (Galactosylsphingosine)

SMILES for CFc000000506 (Galactosylsphingosine)

INCHI for CFc000000506 (Galactosylsphingosine)

Structure for CFc000000506 (Galactosylsphingosine)

3D Structure for CFc000000506 (Galactosylsphingosine)