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Record Information
Version3.6
Creation Date2007-05-24 13:07:33 UTC
Update Date2016-02-11 01:07:36 UTC
HMDB IDHMDB06583
Secondary Accession NumbersNone
Metabolite Identification
Common NamePoly-N-acetyllactosamine
DescriptionPoly-N-acetyllactosamine is a unique carbohydrate composed of N-acetyllactosamine repeats. In particular, poly-N-acetyllactosamine chains are synthesized by repeated alternating additions of N-acetylglucosamine and galactose, catalyzed by -1,3-N-acetylglucosaminyltransferases (poly-N-acetyllactosamine synthase) and -1,4-galactosyltransferases. What is depicted and described in this MetaboCard is a single subunit structure. Poly-N-acetyllactosamine structures occur in mammalian glycoproteins in both N- and O-linked glycans. They represent a backbone for additional modifications by fucosyltransferases, sialyltransferases and sulfotransferases. These glycans have been suggested to be involved in biospecific interactions with selectins and other glycan-binding proteins. Moreover, the poly-Nacetyllactosamine chains in N-glycans have been found to promote tumor progression and metastasis (PMID: 12570780 ).
Structure
Thumb
Synonyms
ValueSource
2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucoseHMDB
2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucose homopolymerHMDB
N-Acetyl-4-O-beta-D-galactopyranosyl-D-glucosamineHMDB
N-Acetyl-lactosamineHMDB
O-beta-D-Galactopyranosyl-(14)-2-deoxy-2-acetamido-D-glucoseHMDB
Poly(N-acetyllactosamine)HMDB
Chemical FormulaC14H25NO11
Average Molecular Weight383.3484
Monoisotopic Molecular Weight383.142760647
IUPAC NameN-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide
CAS Registry Number82441-98-3
SMILES
CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO
InChI Identifier
InChI=1S/C14H25NO11/c1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)/t6-,7+,8+,9+,10-,11-,12+,13+,14-/m0/s1
InChI KeyInChIKey=HESSGHHCXGBPAJ-ZBELOFFLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acyl glycosides. These are compounds containing fatty acyl chain linked to a carbohydrate moiety through a glycosidic bond. Fatty acyl glycosides are composed of a glycosyl moiety (one or several units) 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides
Alternative Parents
Substituents
  • Fatty acyl glycoside
  • Amino sugar
  • Mannosamine
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Amino saccharide
  • Oxane
  • Monosaccharide
  • Beta-hydroxy aldehyde
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility152.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.6ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.24 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity80.86 m3·mol-1ChemAxon
Polarizability35.62 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023985
KNApSAcK IDNot Available
Chemspider ID106753
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06583
Metagene LinkHMDB06583
METLIN ID4231
PubChem Compound119547
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhou D: Why are glycoproteins modified by poly-N-acetyllactosamine glyco-conjugates? Curr Protein Pept Sci. 2003 Feb;4(1):1-9. [12570780 ]

Enzymes

General function:
Involved in N-acetyllactosaminide beta-1,3-N-acetylgluc
Specific function:
Can initiate the synthesis or the elongation of the linear poly-N-acetyllactosaminoglycans.
Gene Name:
B3GNT1
Uniprot ID:
O43505
Molecular weight:
47118.67
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 6 of non- reducing N-acetylglucosamine (GlcNAc) residues of keratan. Mediates sulfation of keratan in cornea. Keratan sulfate plays a central role in maintaining corneal transparency. Acts on the non- reducing terminal GlcNAc of short and long carbohydrate substrates that have poly-N-acetyllactosamine structures
Gene Name:
CHST6
Uniprot ID:
Q9GZX3
Molecular weight:
44098.4
General function:
Involved in acetylglucosaminyltransferase activity
Specific function:
Branching enzyme that converts linear into branched poly-N-acetyllactosaminoglycans. Introduces the blood group I antigen during embryonic development. It is closely associated with the development and maturation of erythroid cells. The expression of the blood group I antigen in erythrocytes is determined by isoform C.
Gene Name:
GCNT2
Uniprot ID:
Q06430
Molecular weight:
45854.405
General function:
Involved in galactosyltransferase activity
Specific function:
Catalyzes the initiation and elongation of poly-N- acetyllactosamine chains
Gene Name:
bGnT-2
Uniprot ID:
Q9NY97
Molecular weight:
46021.6
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 6 of non- reducing N-acetylglucosamine (GlcNAc) residues and O-linked sugars of mucin-type acceptors. Acts on the non-reducing terminal GlcNAc of short carbohydrate substrates. However, it does not transfer sulfate to longer carbohydrate substrates that have poly-N- acetyllactosamine structures. Has no activity toward keratan. Not involved in generating HEV-expressed ligands for L-selectin. Its substrate specificity may be influenced by its subcellular location
Gene Name:
CHST5
Uniprot ID:
Q9GZS9
Molecular weight:
46160.0
General function:
Involved in galactosyltransferase activity
Specific function:
Beta-1,3-galactosyltransferase that transfers galactose from UDP-galactose to substrates with a terminal beta-linked galactose residue. Has a preference for galactose-beta-1,4-xylose that is found in the linker region of glycosaminoglycans, such as heparan sulfate and chondroitin sulfate. Has no activity towards substrates with terminal glucosamine or galactosamine residues.
Gene Name:
B3GALT6
Uniprot ID:
Q96L58
Molecular weight:
37137.08
General function:
Involved in galactosylceramide sulfotransferase activity
Specific function:
Transfers a sulfate to position 3 of non-reducing beta- galactosyl residues in N-glycans and core2-branched O-glycans. Has high activity towards Gal-beta-1,4-GlcNAc, Gal-beta-1,4(Fuc-alpha- 1,3)GlcNAc and lower activity towards Gal-beta-1,3(Fuc-alpha- 1,4)GlcNAc
Gene Name:
GAL3ST3
Uniprot ID:
Q96A11
Molecular weight:
48955.1
General function:
Involved in galactosyltransferase activity
Specific function:
Beta-1,3-N-acetylglucosaminyltransferase that plays a role in the elongation of specific branch structures of multiantennary N-glycans. Has strong activity towards tetraantennary N-glycans and 2,6 triantennary glycans
Gene Name:
B3GNT8
Uniprot ID:
Q7Z7M8
Molecular weight:
43395.4