Record Information
Version3.6
Creation Date2007-05-24 16:11:40 UTC
Update Date2013-05-29 19:44:29 UTC
HMDB IDHMDB06591
Secondary Accession NumbersNone
Metabolite Identification
Common NameLactosamine
DescriptionLactosamine 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
Thumb
Synonyms
  1. 2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose
  2. 2-Amino-2-deoxy-4-O-beta-delta-galactopyranosyl-delta-glucose
  3. beta-D-Galactopyranosyl-(1->4)-2-amino-2-deoxy-D-glucose
  4. beta-D-Galactopyranosyl-(1->4)-D-glucosamine
  5. beta-delta-Galactopyranosyl-(1->4)-2-amino-2-deoxy-delta-glucose
  6. beta-delta-Galactopyranosyl-(1->4)-delta-glucosamine
  7. LACN
  8. Polylactosamine
Chemical FormulaC12H23NO10
Average Molecular Weight341.3117
Monoisotopic Molecular Weight341.132195961
IUPAC Name(2R,3R,4S,5R)-2-amino-3,5,6-trihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal
Traditional IUPAC Namelactosamine
CAS Registry Number13000-25-4
SMILES
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/C12H23NO10/c13-4(1-14)7(18)11(5(17)2-15)23-12-10(21)9(20)8(19)6(3-16)22-12/h1,4-12,15-21H,2-3,13H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1
InChI KeyLAVNEPYDFKGEOD-JVCRWLNRSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassTetrasaccharides
Sub ClassTetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Polyamine
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentTetrahexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
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 solubility342 g/LALOGPS
logP-2.9ALOGPS
logP-5.4ChemAxon
logS0ALOGPS
pKa (strongest acidic)12.12ChemAxon
pKa (strongest basic)7.16ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count8ChemAxon
polar surface area203.16ChemAxon
rotatable bond count8ChemAxon
refractivity71.42ChemAxon
polarizability31.56ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
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 IDFDB019859
KNApSAcK IDNot Available
Chemspider ID106391
KEGG Compound IDC00203
BioCyc IDBETA-D-GALACTOSYL-ETCETERA-GALACTOSAMINY
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06591
Metagene LinkHMDB06591
METLIN ID3675
PubChem Compound119065
PDB IDNot Available
ChEBI ID25001
References
Synthesis ReferencePark W K; Aravind S; Romanowska A; Renaud J; Roy R Syntheses of clustered lactosides by telomerization. Methods in enzymology (1994), 242 294-304.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Henion TR, Schwarting GA: Patterning the developing and regenerating olfactory system. J Cell Physiol. 2007 Feb;210(2):290-7. Pubmed: 17111357

Enzymes

Gene Name:
GALNT7
Uniprot ID:
Q86SF2
Gene Name:
CHSY3
Uniprot ID:
Q70JA7
Gene Name:
CHPF
Uniprot ID:
Q8IZ52
Gene Name:
CHSY1
Uniprot ID:
Q86X52
Gene Name:
GALNT20
Uniprot ID:
Q2L4S5