ChemFOnt: Showing chemical card for Lewis a trisaccharide (CFc000002825)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:48 UTC

Chemfont ID

CFc000002825

Molecule Identification

Common Name

Lewis a trisaccharide

Definition

Lewis a trisaccharide is a fucosyloligosaccharide present in human milk and colostrum. Human colostrum is known to be important for the protection of infants against infection by pathogenic microorganisms. This protection is thought to be due, partially, to various neutral and acidic oligosaccharides that are present in colostrum and milk. Moderate-to-severe diarrhea of all causes occurs less often in infants whose milk contains high levels of total 2-linked fucosyloligosaccharides as a percent of milk oligosaccharide. The trisaccharide Lewis a trisaccharide is identical with the structure for the specific determinant in Lea substance, and strongly inhibits the agglutination of Lea erythrocytes by a human anti-Lea serum. (PMID: 15343178 , 17375110 , 12568665 , 2503806 ; 3809884; 6809837; 6880139; 7701811; 8662894; 8914840; 8943285).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-b-D-Galactopyranosyl-4-O-a-L-fucopyranosyl-N-acetyl-D-glucosamine	HMDB
3-O-beta-D-Galactopyranosyl-4-O-alpha-L-fucopyranosyl-N-acetyl-D-glucosamine	HMDB
Lea	HMDB
Lea tri	HMDB
Lea trisaccharide	HMDB
Lewis a	HMDB
N-Acetyl-4-O-a-L-fucosyl-3-O-b-D-galactosyl-glucosamine	HMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-D-galactosyl-glucosamine	HMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-delta-galactosyl-glucosamine	HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-glucose	HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-glucose	HMDB
O-a-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-delta-glucose	HMDB
N-[(2R,3R,4R,5R)-5,6-Dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidate	Generator, HMDB

Chemical Formula

C₂₀H₃₅NO₁₅

Average Molecular Weight

529.4896

Monoisotopic Molecular Weight

529.200669455

IUPAC Name

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

Traditional Name

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

CAS Registry Number

56570-03-7

SMILES

[H][C@@](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@@H](NC(C)=O)C=O

InChI Identifier

InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1

InChI Key

HHQLEBOUBWWITP-MBKDEEHCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006582)
Cell membrane (HMDB: HMDB0006582)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006582)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006582)

Source

Endogenous

Endogenous (HMDB: HMDB0006582)

Animal

Animal (HMDB: HMDB0006582)

Exogenous

Food

Food (HMDB: HMDB0006582)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006582)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006582)

Lipid metabolism pathway (HMDB: HMDB0006582)

Biochemical process

Lipid transport (HMDB: HMDB0006582)

Role

Biological role

Energy source (HMDB: HMDB0006582)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	121 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.4	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.16 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	111.73 m³·mol⁻¹	ChemAxon
Polarizability	49.38 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

HMDB0006582

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023984

KNApSAcK ID

Not Available

Chemspider ID

30776578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477858

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Makimura, Yutaka; Ishida, Hideharu; Kiso, Makoto; Hasegawa, Akira. Synthetic studies of sialoglycoconjugates. 93. Synthetic studies on tumor-associated antigens: efficient syntheses of Lea and sialyl-Lea oligosaccharides, and their deaminated analogs. ChemInform 28(35) · August 2010

Showing chemical card for Lewis a trisaccharide (CFc000002825)

MOL for CFc000002825 (Lewis a trisaccharide)

3D MOL for CFc000002825 (Lewis a trisaccharide)

3D SDF for CFc000002825 (Lewis a trisaccharide)

3D-SDF for CFc000002825 (Lewis a trisaccharide)

PDB for CFc000002825 (Lewis a trisaccharide)

3D PDB for CFc000002825 (Lewis a trisaccharide)

SMILES for CFc000002825 (Lewis a trisaccharide)

INCHI for CFc000002825 (Lewis a trisaccharide)

Structure for CFc000002825 (Lewis a trisaccharide)

3D Structure for CFc000002825 (Lewis a trisaccharide)