Human Metabolome Database Version 3.5

Showing metabocard for Lactosamine (HMDB06591)

Record Information
Version 3.5
Creation Date 2007-05-24 10:11:40 -0600
Update Date 2013-05-29 13:44:29 -0600
HMDB ID HMDB06591
Secondary Accession Numbers None
Metabolite Identification
Common Name Lactosamine
Description Lactosamine 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C12H23NO10
Average Molecular Weight 341.3117
Monoisotopic Molecular Weight 341.132195961
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 Name lactosamine
CAS Registry Number 13000-25-4
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 Key LAVNEPYDFKGEOD-JVCRWLNRSA-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 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 Parent Tetrahexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
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 342 g/L ALOGPS
LogP -2.93 ALOGPS
LogP -5.4 ChemAxon
LogS 0.00 ALOGPS
pKa (strongest acidic) 12.12 ChemAxon
pKa (strongest basic) 7.16 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 203.16 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 71.42 ChemAxon
Polarizability 31.56 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations Not Available
Tissue Location Not Available
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 FDB019859
KNApSAcK ID Not Available
Chemspider ID 106391 Link_out
KEGG Compound ID C00203 Link_out
BioCyc ID BETA-D-GALACTOSYL-ETCETERA-GALACTOSAMINY Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06591 Link_out
Metagene Link HMDB06591 Link_out
METLIN ID 3675 Link_out
PubChem Compound 119065 Link_out
PDB ID Not Available
ChEBI ID 25001 Link_out
References
Synthesis Reference Park 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 Link_out

Enzymes
Name: Beta-1,4 N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: B4GALNT1
Uniprot ID: Q00973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 4
Reactions: Not Available
Gene Name: GALNT4
Uniprot ID: Q8N4A0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 3
Reactions: Not Available
Gene Name: GALNT3
Uniprot ID: Q14435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable polypeptide N-acetylgalactosaminyltransferase 8
Reactions: Not Available
Gene Name: GALNT8
Uniprot ID: Q9NY28 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase-like protein 2
Reactions: Not Available
Gene Name: GALNTL2
Uniprot ID: Q8N3T1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 1
Reactions: Not Available
Gene Name: GALNTL1
Uniprot ID: Q8N428 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 10
Reactions: Not Available
Gene Name: GALNT10
Uniprot ID: Q86SR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 4
Reactions: Not Available
Gene Name: GALNTL4
Uniprot ID: Q6P9A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylgalactosaminyltransferase 7
Reactions: Not Available
Gene Name: GALNT7
Uniprot ID: Q86SF2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 6
Reactions: Not Available
Gene Name: GALNT6
Uniprot ID: Q8NCL4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 14
Reactions: Not Available
Gene Name: GALNT14
Uniprot ID: Q96FL9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 2
Reactions: Not Available
Gene Name: GALNT2
Uniprot ID: Q10471 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 12
Reactions: Not Available
Gene Name: GALNT12
Uniprot ID: Q8IXK2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: GALNT1
Uniprot ID: Q10472 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 5
Reactions: Not Available
Gene Name: GALNT5
Uniprot ID: Q7Z7M9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-GalNAc:beta-1,3-N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: B3GALNT1
Uniprot ID: O75752 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histo-blood group ABO system transferase
Reactions: Not Available
Gene Name: ABO
Uniprot ID: P16442 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Chondroitin sulfate synthase 3
Reactions: Not Available
Gene Name: CHSY3
Uniprot ID: Q70JA7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Chondroitin sulfate synthase 2
Reactions: Not Available
Gene Name: CHPF
Uniprot ID: Q8IZ52 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Chondroitin sulfate synthase 1
Reactions: Not Available
Gene Name: CHSY1
Uniprot ID: Q86X52 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunit
Reactions: Not Available
Gene Name: OGT
Uniprot ID: O15294 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 13
Reactions: Not Available
Gene Name: GALNT13
Uniprot ID: Q68VI8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 9
Reactions: Not Available
Gene Name: GALNT9
Uniprot ID: Q9HCQ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase-like 6
Reactions: Not Available
Gene Name: GALNTL6
Uniprot ID: Q49A17 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 5
Reactions: Not Available
Gene Name: GALNTL5
Uniprot ID: Q7Z4T8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pp-GalNAc-transferase 20
Reactions: Not Available
Gene Name: GALNT20
Uniprot ID: Q2L4S5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA