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Record Information
Version4.0
Creation Date2007-05-24 13:07:33 UTC
Update Date2017-09-27 08:24:45 UTC
HMDB IDHMDB0006583
Secondary Accession Numbers
  • HMDB06583
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
PNALAMeSH
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 KeyHESSGHHCXGBPAJ-ZBELOFFLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as fatty acyl glycosides of mono- and disaccharides. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentFatty 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
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity80.86 m³·mol⁻¹ChemAxon
Polarizability35.62 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g59-1169000000-63db2012e8740c82b427View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-8941000000-2ca60fa57b84220edb6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-9631000000-58c2e7db43bf8480de15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0230-2459000000-2641dc1f4ac5d1460232View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nvi-6933000000-a34db716f8f4a9226b7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9720000000-40688a14c35dffff6e68View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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. [PubMed: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