Showing metabocard for (N-acetylneuraminosyl(a2-6)lactosamine) (BMDB0001081)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:50 UTC
Update Date2020-06-04 20:03:52 UTC
BMDB IDBMDB0001081
Secondary Accession Numbers
  • BMDB01081
Metabolite Identification
Common Name(N-acetylneuraminosyl(a2-6)lactosamine)
Description(N-Acetylneuraminosyl(a2-6)lactosamine), also known as a-neunac-(2->6)-b-D-gal-(1->4)-b-D-glcnac or 6-sialyllactosamine, belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety (N-Acetylneuraminosyl(a2-6)lactosamine) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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 acidChEBI
(N-Acetylneuraminosyl(alpha2-6)lactosamine)ChEBI
6'-SialyllactosamineChEBI
6-SialyllactosamineChEBI
alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamineChEBI
alpha-N-Acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamineChEBI
alpha-NeuNAc-(2->6)-beta-D-gal-(1->4)-beta-D-glcnacChEBI
alpha-NeupNAc-(2->6)-beta-D-galp-(1->4)-beta-D-glcpnacChEBI
N-Acetylneuraminosyl(alpha2-6)lactosamineChEBI
Neu5aca2-6galb1-4glcnacbChEBI
Neuac-lactChEBI
NeuAcalpha2,6galbeta1,4glcnacChEBI
Neuacalpha2,6galnacbeta1,4glcnacChEBI
Neuacalpha2-6galbeta1-4glcnacbetaChEBI
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-glucopyranoseChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(26)-O-beta-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoseChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranoseChEBI
WURCS=2.0/3,3,2/[a2122h-1b_1-5_2*ncc/3=o][a2112h-1b_1-5][aad21122h-2a_2-6_5*ncc/3=o]/1-2-3/a4-b1_b6-C2ChEBI
(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-carboxylateGenerator
(N-Acetylneuraminosyl(α2-6)lactosamine)Generator
a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamineGenerator
Α-N-acetylneuraminyl-2,6-β-D-galactosyl-1,4-N-acetyl-β-D-glucosamineGenerator
a-N-Acetylneuraminyl-2,6-b-delta-galactosyl-1,4-N-acetyl-b-delta-glucosamineGenerator
Α-N-acetylneuraminyl-2,6-β-δ-galactosyl-1,4-N-acetyl-β-δ-glucosamineGenerator
a-NeuNAc-(2->6)-b-D-gal-(1->4)-b-D-glcnacGenerator
Α-neunac-(2->6)-β-D-gal-(1->4)-β-D-glcnacGenerator
a-NeupNAc-(2->6)-b-D-galp-(1->4)-b-D-glcpnacGenerator
Α-neupnac-(2->6)-β-D-galp-(1->4)-β-D-glcpnacGenerator
N-Acetylneuraminosyl(a2-6)lactosamineGenerator
N-Acetylneuraminosyl(α2-6)lactosamineGenerator
O-(N-Acetyl-a-neuraminosyl)-(26)-O-b-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-D-glucopyranoseGenerator
O-(N-Acetyl-α-neuraminosyl)-(26)-O-β-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-D-glucopyranoseGenerator
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-delta-glucopyranoseGenerator
O-(N-Acetyl-α-neuraminosyl)-(2->6)-O-β-δ-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-δ-glucopyranoseGenerator
Neu5acbeta2-6galbeta1-4glcnacbetaChEBI, HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranoseHMDB
a-N-Acetylneuraminyl-(2->6)-b-D-galactosyl-(1->4)-N-acetyl-b-D-glucosamineGenerator, HMDB
Α-N-acetylneuraminyl-(2->6)-β-D-galactosyl-(1->4)-N-acetyl-β-D-glucosamineGenerator, HMDB
Chemical FormulaC25H42N2O19
Average Molecular Weight674.603
Monoisotopic Molecular Weight674.238177172
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 Name6-sialyllactosamine
CAS Registry Number64364-50-7
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 KeyRPSBVJXBTXEJJG-LURNZOHQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentNeuraminic acids
Alternative Parents
Substituents
  • Neuraminic acid
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Pyran
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and 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-2.7ALOGPS
logP-7.4ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area343.95 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity139.71 m³·mol⁻¹ChemAxon
Polarizability63.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified13.341 - 17.788 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001081
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022413
KNApSAcK IDNot Available
Chemspider ID111381
KEGG Compound IDC04886
BioCyc IDALPHA-N-ACETYLNEURAMINYL-26-BETA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17725
References
Synthesis ReferenceDall'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. Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.