ChemFOnt: Showing chemical card for Lactosamine (CFc000002832)

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

CFc000002832

Molecule Identification

Common Name

Lactosamine

Definition

Lactosamine is a disaccharide composed of galactose b1,4-linked to N-acetylglucosamine, and is a common constituent of complex N-linked glycans in metazoans. Unmodified terminal lactosamine, however, is less typical in tissues, since it is often further modified by additional substitutions, such as fucose, sialic acid, or sulfate to form a number of significant receptor and signaling molecules. Lactosamine-containing glycans are also required for proper targeting and maintenance of olfactory axons, and may also function in other sensory regions.(PMID: 17111357 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₄H₄₆N₂O₂₀

Average Molecular Weight

682.6234

Monoisotopic Molecular Weight

682.264391922

IUPAC Name

2-amino-3,5,6-trihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; 2-{[5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-amino-3,5,6-trihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; 2-{[5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

13000-25-4

SMILES

NC(C=O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO.NC1C(O)OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/2C12H23NO10/c13-5-7(17)10(4(2-15)21-11(5)20)23-12-9(19)8(18)6(16)3(1-14)22-12;13-4(1-14)7(18)11(5(17)2-15)23-12-10(21)9(20)8(19)6(3-16)22-12/h3-12,14-20H,1-2,13H2;1,4-12,15-21H,2-3,13H2

InChI Key

PLXWPPSZXBDZCI-UHFFFAOYSA-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
Disaccharide
Glycosyl compound
O-glycosyl compound
Amino saccharide
Beta-hydroxy aldehyde
Oxane
Secondary alcohol
1,2-aminoalcohol
Hemiacetal
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary amine
Hydrocarbon derivative
Primary aliphatic amine
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Amine
Organic nitrogen compound
Aldehyde
Alcohol
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006591)

Organelle

Endoplasmic reticulum (HMDB: HMDB0006591)
Golgi apparatus (HMDB: HMDB0006591)
Lysosome (HMDB: HMDB0006591)

Source

Endogenous

Endogenous (HMDB: HMDB0006591)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	342 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-4.8	ChemAxon
logS	0	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	195.32 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	69.99 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019859

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

Park W K; Aravind S; Romanowska A; Renaud J; Roy R Syntheses of clustered lactosides by telomerization. Methods in enzymology (1994), 242 294-304.

Showing chemical card for Lactosamine (CFc000002832)

MOL for CFc000002832 (Lactosamine)

3D MOL for CFc000002832 (Lactosamine)

3D SDF for CFc000002832 (Lactosamine)

3D-SDF for CFc000002832 (Lactosamine)

PDB for CFc000002832 (Lactosamine)

3D PDB for CFc000002832 (Lactosamine)

SMILES for CFc000002832 (Lactosamine)

INCHI for CFc000002832 (Lactosamine)

Structure for CFc000002832 (Lactosamine)

3D Structure for CFc000002832 (Lactosamine)