5-acetamido-2-({2-[(5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

• ChemBase ID: 133631
• Molecular Formular: C25H42N2O19
• Molecular Mass: 674.60298
• Monoisotopic Mass: 674.23817713
• SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC1C(C(OC(C1O)OC(C(CO)O)C(C(C=O)NC(=O)C)O)CO)O)O
• Canonical SMILES: OCC(C(C(C(NC(=O)C)C=O)O)OC1OC(CO)C(C(C1O)OC1(CC(O)C(C(O1)C(C(CO)O)O)NC(=O)C)C(=O)O)O)O
• InChI: InChI=1S/C25H42N2O19/c1-8(32)26-10(4-28)16(37)20(13(36)6-30)44-23-19(40)22(18(39)14(7-31)43-23)46-25(24(41)42)3-11(34)15(27-9(2)33)21(45-25)17(38)12(35)5-29/h4,10-23,29-31,34-40H,3,5-7H2,1-2H3,(H,26,32)(H,27,33)(H,41,42)
• InChIKey: RGZDLTASXRMKKF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-acetamido-2-({2-[(5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• IUPAC Traditional name: 5-acetamido-2-({2-[(5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• Synonyms: α-NeuNAc-(2→3)-β-D-Gal-(1→4)-D-GlcNAc; 3′-SLN; 3′-Sialyl-N-acetyllactosamine; 3′-N-Acetylneuraminyl-N-acetyllactosamine sodium salt

Database IDs

• CAS Number: 81693-22-3
• MDL Number: MFCD00132996
• PubChem SID: 24891158; 162227908
• PubChem CID: 4150746

CALCULATED PROPERTIES

• Acid pKa: 2.8378649
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -10.637272
• LogD (pH = 7.4): -11.520468
• Log P: -8.029466
• Molar Refractivity: 141.1315 cm^3
• Polarizability: 58.224663 Å^3
• Polar Surface Area: 351.79 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A6936

Application
3′-N-Acetylneuraminyl-N-acetyllactosamine is a glycan component of O-gylcopeptides. 3′-Sialyl-N-acetyllactosamine can be used to make an avian receptor analogue glycoprobe to study the binding of influenza viruses such as the North American lineage subtype H7N2 virus A/New York/107/2003 (NY107). 3′-Sialyl-N-acetyllactosamine is used as a reference material in the analysis of milk oligosaccharides.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A6936.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.