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

• ChemBase ID: 155797
• Molecular Formular: C48H79N3O37
• Molecular Mass: 1290.13876
• Monoisotopic Mass: 1289.43924048
• 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)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)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)O)CO)CO)O)NC(=O)C)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O[C@@]1(C[C@@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](CO[C@@]3(C[C@H](O)[C@H]([C@@H](O3)[C@@H]([C@@H](CO)O)O)NC(=O)C)C(=O)O)O[C@H]([C@@H]2NC(=O)C)O[C@H]2[C@@H](O)[C@@H](CO)O[C@H]([C@@H]2O)O[C@H]2[C@@H](CO)OC([C@@H]([C@H]2O)O)O)[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/C48H79N3O37/c1-12(57)49-23-15(60)4-47(45(74)75,86-37(23)26(64)17(62)6-52)78-11-22-30(68)36(25(51-14(3)59)42(82-22)85-39-28(66)19(8-54)80-43(33(39)71)83-35-21(10-56)79-41(73)32(70)31(35)69)84-44-34(72)40(29(67)20(9-55)81-44)88-48(46(76)77)5-16(61)24(50-13(2)58)38(87-48)27(65)18(63)7-53/h15-44,52-56,60-73H,4-11H2,1-3H3,(H,49,57)(H,50,58)(H,51,59)(H,74,75)(H,76,77)/t15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25+,26+,27+,28-,29-,30+,31+,32+,33+,34+,35-,36+,37+,38+,39-,40-,41?,42-,43-,44-,47+,48-/m0/s1
• InChIKey: FCIROHDMPFOSFG-SRQCWDAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-3-hydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-3-hydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: α-Neu5Ac-(2→3)-β-Gal-(1→3)-[α-Neu5Ac-(2→6)]-β-GlcNAc-(1→3)-β-Gal-(1→4)-Glc; Disialyllacto-N-tetraose

Database IDs

• CAS Number: 61278-38-4
• PubChem SID: 162249935
• PubChem CID: 71312225

CALCULATED PROPERTIES

• Acid pKa: 2.5642266
• H Acceptors: 37
• H Donor: 24
• LogD (pH = 5.5): -18.504808
• LogD (pH = 7.4): -20.314743
• Log P: -13.337549
• Molar Refractivity: 264.8072 cm^3
• Polarizability: 110.67225 Å^3
• Polar Surface Area: 647.8 Å^2
• Rotatable Bonds: 25
• 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

Product Information

• Purity: ≥95.0% (TLC)
• Empirical Formula (Hill Notation): C48H79N3O37

DETAILS

Sigma Aldrich - 68656

Application
Disialyllacto-N-tetraose, is a milk oligosaccharide, used to prevents necrotising enterocolitis in neonates. Disialyllacto-N-tetraose is used as a reference molecule in procedures that measure slialylated oligosaccharides from milk.