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

• ChemBase ID: 155809
• Molecular Formular: C25H42N2O19
• Molecular Mass: 674.60298
• Monoisotopic Mass: 674.23817713
• SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O[C@H]1[C@H]([C@H](O[C@H]([C@@H]1O)O[C@@H]1[C@H](OC([C@@H]([C@H]1O)O)NC(=O)C)CO)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)OC([C@@H]([C@H]2O)O)NC(=O)C)[C@@H]([C@H]([C@H]1O)O[C@]1(C[C@H](O)[C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)C(=O)O)O
• InChI: InChI=1S/C25H42N2O19/c1-7(31)26-13-9(33)3-25(24(40)41,45-20(13)14(35)10(34)4-28)46-21-15(36)11(5-29)43-23(18(21)39)44-19-12(6-30)42-22(27-8(2)32)17(38)16(19)37/h9-23,28-30,33-39H,3-6H2,1-2H3,(H,26,31)(H,27,32)(H,40,41)/t9-,10+,11+,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22?,23-,25+/m0/s1
• InChIKey: HUNVSYPDCXFGLB-KROWHOKKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 3′-Sialyl-N-acetyllactosamine

Database IDs

• CAS Number: 102490-37-9
• MDL Number: MFCD03095477
• PubChem SID: 24872593; 162249947
• PubChem CID: 16213476

CALCULATED PROPERTIES

• Acid pKa: 2.8378649
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -10.001451
• LogD (pH = 7.4): -10.884663
• Log P: -7.393644
• Molar Refractivity: 139.7093 cm^3
• Polarizability: 58.127914 Å^3
• Polar Surface Area: 343.95 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Empirical Formula (Hill Notation): C25H42N2O19

DETAILS

Sigma Aldrich - 49071

Application
3′-Sialyl-N-acetyllactosamine is a low molecular weight acceptor molecule precursor of the nonreducing terminal tetrasaccharide Sda blood group structure. 3′-Sialyl-N-acetyllactosamine, is used as an avian receptor analogue for North American lineage subtype H7N2 virus A/New York/107/2003 (NY107).