Human Metabolome Database Version 3.5

Showing metabocard for N-Acetyllactosamine (HMDB01542)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:44 -0700
HMDB ID HMDB01542
Secondary Accession Numbers None
Metabolite Identification
Common Name N-Acetyllactosamine
Description N-Acetyllactosamine is an intermediate in the biosynthesis of Keratan sulfate and the biosynthesis of N-Glycan. It is a substrate for Beta-1,4-galactosyltransferase 4, Beta-1,4-galactosyltransferase 2, Beta-1,4-galactosyltransferase 1, Beta-1,4-galactosyltransferase 3 and CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,6-sialyltransferase.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamine
  2. beta-D-Galactosyl-1,4-N-acetyl-D-glucosamine
  3. beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamine
  4. beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamine
  5. D-Galactopyranosyl
  6. delta-Galactopyranosyl
  7. N-Acetyl-Lactosamine
  8. N-Acetyllactosamine
Chemical Formula C14H25NO11
Average Molecular Weight 383.3484
Monoisotopic Molecular Weight 383.142760647
IUPAC Name N-[(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 IUPAC Name N-acetyllactosamine
CAS Registry Number 32181-59-2
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 Key KFEUJDWYNGMDBV-LODBTCKLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Tetrasaccharides
Sub Class Tetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Tetrahexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Keratan sulfate biosynthesis
  • Component of N-Glycan biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 259 g/L ALOGPS
LogP -2.80 ALOGPS
LogP -5 ChemAxon
LogS -0.17 ALOGPS
pKa (strongest acidic) 11.5 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 198.4 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 79.44 ChemAxon
Polarizability 35.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Intestine
  • Epidermis
  • Spleen
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB019860
KNApSAcK ID Not Available
Chemspider ID 388404 Link_out
KEGG Compound ID C00611 Link_out
BioCyc ID BETA-D-GALACTOSYL-ETCETERA-GLUCO Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01542 Link_out
Metagene Link HMDB01542 Link_out
METLIN ID 4231 Link_out
PubChem Compound 439271 Link_out
PDB ID Not Available
ChEBI ID 16153 Link_out
References
Synthesis Reference Dekany, 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) Download (PDF)
General References
  1. Jung SK, Fujimoto D: A novel beta-galactoside-binding lectin in adult rat kidney. J Biochem (Tokyo). 1994 Sep;116(3):547-53. Pubmed: 7852273 Link_out
  2. Yu LC, Twu YC, Chang CY, Lin M: Molecular basis of the adult i phenotype and the gene responsible for the expression of the human blood group I antigen. Blood. 2001 Dec 15;98(13):3840-5. Pubmed: 11739194 Link_out
  3. Dabelsteen E, Buschard K, Hakomori S, Young WW: Pattern of distribution of blood group antigens on human epidermal cells during maturation. J Invest Dermatol. 1984 Jan;82(1):13-7. Pubmed: 6361167 Link_out
  4. Ahmed H, Pohl J, Fink NE, Strobel F, Vasta GR: The primary structure and carbohydrate specificity of a beta-galactosyl-binding lectin from toad (Bufo arenarum Hensel) ovary reveal closer similarities to the mammalian galectin-1 than to the galectin from the clawed frog Xenopus laevis. J Biol Chem. 1996 Dec 20;271(51):33083-94. Pubmed: 8955156 Link_out
  5. Hosomi O, Takeya A: The relationship between the (beta 1-3) N-acetylglucosaminyltransferase and the presence of oligosaccharides containing lacto-N-triose II structure in bovine and human milk. Nippon Juigaku Zasshi. 1989 Feb;51(1):1-6. Pubmed: 2522567 Link_out
  6. Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. Pubmed: 1366057 Link_out
  7. Jinno K, Moriwaki S, Govindarajan S, Okada Y, Tsuji T: Blood group antigens in the intrahepatic biliary tree. II. Type 1 chain N-acetyllactosamine-related carbohydrate antigens in the proliferated bile ductules. J Hepatol. 1989 May;8(3):330-7. Pubmed: 2732447 Link_out
  8. Takeya A, Hosomi O, Kogure T: The presence of N-acetyllactosamine and lactose: beta (1-3)N-acetylglucosaminyltransferase activity in human urine. Jpn J Med Sci Biol. 1985 Feb;38(1):1-8. Pubmed: 3160874 Link_out
  9. Draberova L, Cerna H, Brodska H, Boubelik M, Watt SM, Stanners CP, Draber P: Soluble isoforms of CEACAM1 containing the A2 domain: increased serum levels in patients with obstructive jaundice and differences in 3-fucosyl-N-acetyl-lactosamine moiety. Immunology. 2000 Oct;101(2):279-87. Pubmed: 11012782 Link_out
  10. Kojima S, Eguchi H, Ookawara T, Fujiwara N, Yasuda J, Nakagawa K, Yamamura T, Suzuki K: Clostridium botulinum type A progenitor toxin binds to Intestine-407 cells via N-acetyllactosamine moiety. Biochem Biophys Res Commun. 2005 Jun 3;331(2):571-6. Pubmed: 15850798 Link_out
  11. Hosomi O, Takeya A, Kogure T: Human serum contains N-acetyllactosamine: beta 1-3 N-acetylglucosaminyltransferase activity. J Biochem (Tokyo). 1984 Jun;95(6):1655-9. Pubmed: 6236210 Link_out
  12. Dabelsteen E, Holbrook K, Clausen H, Hakomori S: Cell surface carbohydrate changes during embryonic and fetal skin development. J Invest Dermatol. 1986 Jul;87(1):81-5. Pubmed: 3522754 Link_out
  13. Argueso P, Spurr-Michaud S, Tisdale A, Gipson IK: Variation in the amount of T antigen and N-acetyllactosamine oligosaccharides in human cervical mucus secretions with the menstrual cycle. J Clin Endocrinol Metab. 2002 Dec;87(12):5641-8. Pubmed: 12466366 Link_out

Enzymes
Name: Carbohydrate sulfotransferase 3
Reactions: Not Available
Gene Name: CHST3
Uniprot ID: Q7LGC8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 1
Reactions: Not Available
Gene Name: CHST1
Uniprot ID: O43916 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 2
Reactions:
Uridine diphosphategalactose + N-Acetyl-D-glucosamine unknown Uridine 5'-diphosphate + N-Acetyllactosamine details
Gene Name: B4GALT2
Uniprot ID: O60909 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 1
Reactions:
Uridine diphosphategalactose + N-Acetyl-D-glucosamine unknown Uridine 5'-diphosphate + N-Acetyllactosamine details
Gene Name: B4GALT1
Uniprot ID: P15291 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 7
Reactions: Not Available
Gene Name: CHST7
Uniprot ID: Q9NS84 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 3
Reactions:
Uridine diphosphategalactose + N-Acetyl-D-glucosamine unknown Uridine 5'-diphosphate + N-Acetyllactosamine details
Gene Name: B4GALT3
Uniprot ID: O60512 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 4
Reactions:
Uridine diphosphategalactose + N-Acetyl-D-glucosamine unknown Uridine 5'-diphosphate + N-Acetyllactosamine details
Gene Name: B4GALT4
Uniprot ID: O60513 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Killer cell lectin-like receptor subfamily B member 1
Reactions: Not Available
Gene Name: KLRB1
Uniprot ID: Q12918 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA