Showing metabocard for N-Acetyllactosamine (BMDB0001542)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:26 UTC
Update Date2020-05-11 20:53:28 UTC
BMDB IDBMDB0001542
Secondary Accession Numbers
  • BMDB01542
Metabolite Identification
Common NameN-Acetyllactosamine
DescriptionN-Acetyllactosamine, also known as galb1-4glcnacb or lacnac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyllactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyllactosamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Galactosyl-1,4-N-acetyl-D-glucosamineChEBI
Galb1-4glcnacbChEBI
Galbeta1-4glcnacbetaChEBI
LacNAcChEBI
N-Acetyl-beta-lactosamineChEBI
beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamineKegg
b-D-Galactosyl-1,4-N-acetyl-D-glucosamineGenerator
Β-D-galactosyl-1,4-N-acetyl-D-glucosamineGenerator
N-Acetyl-b-lactosamineGenerator
N-Acetyl-β-lactosamineGenerator
b-D-Galactosyl-1,4-N-acetyl-b-D-glucosamineGenerator
Β-D-galactosyl-1,4-N-acetyl-β-D-glucosamineGenerator
beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamineHMDB
beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamineHMDB
D-GalactopyranosylHMDB
delta-GalactopyranosylHMDB
N-Acetyl-lactosamineHMDB
ACETYL lactosamineHMDB
Chemical FormulaC14H25NO11
Average Molecular Weight383.3484
Monoisotopic Molecular Weight383.142760647
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-acetyllactosamine
CAS Registry Number32181-59-2
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
InChI Identifier
InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1
InChI KeyKFEUJDWYNGMDBV-LODBTCKLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-galactopyranosyl-(1->4)-N-acetyl-D-glucosamine (CHEBI:16153 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-5ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area198.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.44 m³·mol⁻¹ChemAxon
Polarizability35.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Intestine
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001542
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019860
KNApSAcK IDNot Available
Chemspider ID388404
KEGG Compound IDC00611
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetyllactosamine
METLIN ID4231
PubChem Compound439271
PDB IDNot Available
ChEBI ID16153
References
Synthesis ReferenceDekany, Gyula; Agoston, Karoly; Bajza, Istvan; Boejstrup, Marie; Kroeger, Lars. Process for the large-scale preparation of N-acetyllactosamine, lactosamine, lactosamine salts and lactosamine-containing oligosaccharides. PCT Int. Appl. (2007), 44pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Beta-1,4-galactosyltransferase 1
General function:
Involved in alpha-tubulin binding
Specific function:
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT1
Uniprot ID:
P08037
Molecular weight:
44843.0
Enzyme Details
2. Beta-1,4-galactosyltransferase 3
General function:
Involved in beta-N-acetylglucosaminylglycopeptide beta-
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT3
Uniprot ID:
Q5EA87
Molecular weight:
44371.0
Enzyme Details
3. Beta-galactoside alpha-2,6-sialyltransferase 2
General function:
Involved in beta-galactoside alpha-2,6-sialyltransferas
Specific function:
Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates. Has alpha-2,6-sialyltransferase activity toward oligosaccharides that have the Gal-beta-1,4-GlcNAc sequence at the non-reducing end of their carbohydrate groups, but it has weak or no activities toward glycoproteins and glycolipids.
Gene Name:
ST6GAL2
Uniprot ID:
A5D7T4
Molecular weight:
55418.0