ChemFOnt: Showing chemical card for N-Acetyl-6-O-L-fucosyl-D-glucosamine (CFc000001500)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:08 UTC

Chemfont ID

CFc000001500

Molecule Identification

Common Name

N-Acetyl-6-O-L-fucosyl-D-glucosamine

Definition

N-Acetyl-6-O-L-fucosyl-D-glucosamine is an oligosaccharin obtained from human milk (Fiziologiya i Biokhimiya Kul'turnykh Rastenii (2002), 34(1), 52-57).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-L-galactopyranosyl)-D-glucose	HMDB
N-[(2R,3R,4S)-3,4,5-Trihydroxy-1-oxo-6-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidate	Generator, HMDB

Chemical Formula

C₁₄H₂₅NO₁₀

Average Molecular Weight

367.349

Monoisotopic Molecular Weight

367.147846025

IUPAC Name

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

Traditional Name

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

CAS Registry Number

109582-58-3

SMILES

C[C@@H]1OC(OCC(O)[C@@H](O)[C@H](O)[C@@H](NC(C)=O)C=O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C14H25NO10/c1-5-9(19)12(22)13(23)14(25-5)24-4-8(18)11(21)10(20)7(3-16)15-6(2)17/h3,5,7-14,18-23H,4H2,1-2H3,(H,15,17)/t5-,7-,8?,9+,10+,11+,12+,13-,14?/m0/s1

InChI Key

YBWAUUBLHOFOPK-SOHGFDPZSA-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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Amino saccharide
Beta-hydroxy aldehyde
Monosaccharide
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aldehyde
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
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: HMDB0002220)
Cell membrane (HMDB: HMDB0002220)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002220)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002220)

Source

Endogenous

Endogenous (HMDB: HMDB0002220)

Animal

Animal (HMDB: HMDB0002220)

Exogenous

Food

Food (HMDB: HMDB0002220)

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: HMDB0002220)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002220)

Lipid metabolism pathway (HMDB: HMDB0002220)

Biochemical process

Lipid transport (HMDB: HMDB0002220)

Role

Biological role

Energy source (HMDB: HMDB0002220)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	102 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.6	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	79.32 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002220

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022914

KNApSAcK ID

Not Available

Chemspider ID

17216173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833588

PDB ID

Not Available

ChEBI ID

172599

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetyl-6-O-L-fucosyl-D-glucosamine (CFc000001500)

MOL for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

3D MOL for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

3D SDF for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

3D-SDF for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

PDB for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

3D PDB for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

SMILES for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

INCHI for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

Structure for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)

3D Structure for CFc000001500 (N-Acetyl-6-O-L-fucosyl-D-glucosamine)