6-Sialyllactosamine (CHEM035065)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:27:32 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035065
Identification
Common Name6-Sialyllactosamine
ClassSmall Molecule
DescriptionAn amino trisaccharide consisting of an N-acetyl-alpha-neuraminyl residue attached to the galactose residue of N-acetyllactosamine via an alpha-(2->6)-linkage.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass674.603 g/mol
Monoisotopic Mass674.238 g/mol
CAS Registry Number64364-50-7
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility72.5 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-5235119000-5a6aa8ff9e0838274a4bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avi-0051009000-92d7600cf12a3e43b8daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-2294002000-8d29637be46c1d8fd36fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022c-4391001000-847f9d4addc27d2b4d8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-4942473000-7edd91cc87dbeead8022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-9881203000-a60297bc793daed18eb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9641000000-bc983c803272c7ccce3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0020039000-18d48851f2beb9db3adfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3090022000-8c7f3399bee970f68a60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9520001000-9d39a2f319fe4cae1e7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-6626f23b078e7b6b89e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0267029000-d0aa4fdac515d5c38553Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8c-4987000000-3cdf54155f61766e6711Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001081
FooDB IDFDB022413
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDALPHA-N-ACETYLNEURAMINYL-26-BETA
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID111381
ChEBI ID17725
PubChem Compound IDNot Available
Kegg Compound IDC04886
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10619708
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10683228
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10940350
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11425186
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11685546
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12954214
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19443021
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25568069
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31537530
10. International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579