ChemFOnt: Showing chemical card for Galabiosylceramide (d18:1/25:0) (CFc000002214)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:02 UTC

Chemfont ID

CFc000002214

Molecule Identification

Common Name

Galabiosylceramide (d18:1/25:0)

Definition

Galabiosylceramide is a non-acidic diglycosphingolipids, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit. It is a vital component of cellular membranes of most eukaryotic organisms and some bacteria. Its abundance relative to other lipids is usually low other than in epithelial and neuronal cells. Galabiosylceramide has also been found in small amounts in kidney and pancreas, for example. Galabiosylceramide is one of the lipids that accumulates in excessive amounts in Fabry's disease. It is the precursor of the gala series of oligoglycosylceramides. An animal tissues, biosynthesis involves addition of a second monosaccharides unit from the appropriate sugar nucleotide to a monoglycosylceramide, catalysed by a glycosyl transferase, in the lumen of the Golgi apparatus. Glycolipids are important components of the body's immune defense system, either in haptenic reactivity or in antibody-producing potency, i.e. as cellular immunogens or antigens. Certain glycolipids are involved in the antigenicity of blood group determinants, while others bind to specific toxins or bacteria. Some also function as receptors for cellular recognition, and they can be specific for particular tissues or tumours.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₅H₁₀₅NO₁₃

Average Molecular Weight

988.4211

Monoisotopic Molecular Weight

987.758592451

IUPAC Name

N-(1-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl)pentacosanimidic acid

Traditional Name

N-(1-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl)pentacosanimidic acid

CAS Registry Number

77538-38-6

SMILES

[H]C(O)(C=CCCCCCCCCCCCCC)C([H])(CO[C@]1([H])O[C@]([H])(CO)[C@]([H])(O[C@@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C55H105NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-47(60)56-43(44(59)38-36-34-32-30-28-26-16-14-12-10-8-6-4-2)42-66-54-52(65)50(63)53(46(41-58)68-54)69-55-51(64)49(62)48(61)45(40-57)67-55/h36,38,43-46,48-55,57-59,61-65H,3-35,37,39-42H2,1-2H3,(H,56,60)/t43?,44?,45-,46-,48+,49+,50-,51-,52-,53+,54-,55-/m1/s1

InChI Key

WPIHMWBQRSAMDE-QDKMBXLDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosyl-N-acylsphingosines

Alternative Parents

Substituents

Glycosyl-n-acylsphingosine
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acyl
Oxane
N-acyl-amine
Fatty amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0004841)
Golgi apparatus (HMDB: HMDB0004841)

Source

Exogenous

Exogenous (HMDB: HMDB0004841)

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: HMDB0004841)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0027 g/L	ALOGPS
logP	7.62	ALOGPS
logP	12.14	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.81	ChemAxon
pKa (Strongest Basic)	2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	231.35 Å²	ChemAxon
Rotatable Bond Count	45	ChemAxon
Refractivity	272.53 m³·mol⁻¹	ChemAxon
Polarizability	122.88 Å³	ChemAxon
Number of Rings	2	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

FDB023442

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Galabiosylceramide (d18:1/25:0) (CFc000002214)

MOL for CFc000002214 (Galabiosylceramide (d18:1/25:0))

3D MOL for CFc000002214 (Galabiosylceramide (d18:1/25:0))

3D SDF for CFc000002214 (Galabiosylceramide (d18:1/25:0))

3D-SDF for CFc000002214 (Galabiosylceramide (d18:1/25:0))

PDB for CFc000002214 (Galabiosylceramide (d18:1/25:0))

3D PDB for CFc000002214 (Galabiosylceramide (d18:1/25:0))

SMILES for CFc000002214 (Galabiosylceramide (d18:1/25:0))

INCHI for CFc000002214 (Galabiosylceramide (d18:1/25:0))

Structure for CFc000002214 (Galabiosylceramide (d18:1/25:0))

3D Structure for CFc000002214 (Galabiosylceramide (d18:1/25:0))