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Showing metabocard for (N-acetylneuraminosyl(a2-6)lactosamine) (HMDB01081)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:51 -0700
HMDB ID HMDB01081
Secondary Accession Numbers
  • HMDB02049
  • HMDB06609
Metabolite Identification
Common Name (N-acetylneuraminosyl(a2-6)lactosamine)
Description

(N-acetylneuraminosyl(alpha2-6)lactosamine) is widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,6-linked to N-acetylgalactosamine (GalNAc). The biosynthesis of the linkage is mediated by a member of the sialyltransferase family, the beta-galactoside alpha,6-sialyltransferase (EC 2.4.99.1, ST6Gal.I). Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. (PMID 11425186 Link_out)

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6'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228 Link_out)

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Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (N-acetylneuraminosyl(alpha2-6)lactosamine)
  2. 6'-Sialyllactosamine
  3. a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamine
  4. alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
  5. alpha-N-Acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamine
  6. NeuAcalpha2,6Galbeta1,4GlcNAc
  7. O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-Glucopyranose
  8. O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-Glucopyranose
  9. O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-Glucopyranose
Chemical Formula C25H42N2O19
Average Molecular Weight 674.603
Monoisotopic Molecular Weight 674.238177172
IUPAC Name (2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional IUPAC Name 6-sialyllactosamine
CAS Registry Number 64364-50-7
SMILES [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1
InChI Key RPSBVJXBTXEJJG-LURNZOHQSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Trisaccharides
Sub Class Trihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • Acetal
  • Carboxamide Group
  • Carboxylic Acid
  • Glucosamine
  • Glyco Amino Acid
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • N Acetylneuraminic Acid
  • Neuraminic Acid
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Pyranoid Amino Acid
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sugar Acid
Direct Parent Trihexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
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 72.5 g/L ALOGPS
LogP -2.70 ALOGPS
LogP -7.4 ChemAxon
LogS -0.97 ALOGPS
pKa (strongest acidic) 2.89 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 13 ChemAxon
Polar Surface Area 343.95 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 139.71 ChemAxon
Polarizability 63.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Breast Milk
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Breast Milk Detected and Quantified
Article_icon
250.2962012 uM Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022413
KNApSAcK ID Not Available
Chemspider ID 111381 Link_out
KEGG Compound ID C04886 Link_out
BioCyc ID ALPHA-N-ACETYLNEURAMINYL-26-BETA Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01081 Link_out
Metagene Link HMDB01081 Link_out
METLIN ID 5990 Link_out
PubChem Compound 125128 Link_out
PDB ID Not Available
ChEBI ID 17725 Link_out
References
Synthesis Reference Dall'Olio F The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconjugate journal (2000), 17(10), 669-76.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. Pubmed: 11425186 Link_out
  2. Huynh QK, Shailubhai K, Boddupalli H, Yu HH, Broschat KO, Jacob GS: Isolation and characterization from porcine serum of a soluble sulfotransferase responsible for 6-O-sulfation of the galactose residue in 2'-fucosyllactose: implications in the synthesis of the ligand for L-selectin. Glycoconj J. 1999 Jul;16(7):357-63. Pubmed: 10619708 Link_out
  3. Manzella SM, Dharmesh SM, Cohick CB, Soares MJ, Baenziger JU: Developmental regulation of a pregnancy-specific oligosaccharide structure, NeuAcalpha2,6GalNAcbeta1,4GlcNAc, on select members of the rat placental prolactin family. J Biol Chem. 1997 Feb 21;272(8):4775-82. Pubmed: 9030532 Link_out
  4. Britten CJ, McDowell W, Kelly VA, De Vries T, Van den Eijnden DH, Bird MI: Fucosylation of sialyllactosamine chains by the human leukocyte alpha 3 fucosyltransferase; FucT-VII. Biochem Soc Trans. 1997 Aug;25(3):425S. Pubmed: 9388652 Link_out
  5. Muthing J, Meisen I, Bulau P, Langer M, Witthohn K, Lentzen H, Neumann U, Peter-Katalinic J: Mistletoe lectin I is a sialic acid-specific lectin with strict preference to gangliosides and glycoproteins with terminal Neu5Ac alpha 2-6Gal beta 1-4GlcNAc residues. Biochemistry. 2004 Mar 23;43(11):2996-3007. Pubmed: 15023051 Link_out
  6. Toma V, Zuber C, Winter HC, Goldstein IJ, Roth J: Application of a lectin from the mushroom Polysporus squamosus for the histochemical detection of the NeuAcalpha2,6Galbeta1,4Glc/GlcNAc sequence of N-linked oligosaccharides: a comparison with the Sambucus nigra lectin. Histochem Cell Biol. 2001 Aug;116(2):183-93. Pubmed: 11685546 Link_out