2-[(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy]-4-hydroxy-3-(sulfooxy)-3,4-dihydro-2H-pyran-6-carboxylic acid sodium

• ChemBase ID: 133122
• Molecular Formular: C14H21NNaO14S
• Molecular Mass: 482.36961
• Monoisotopic Mass: 482.05804464
• SMILES: CC(=O)NC(C=O)C(C(C(CO)O)O)OC1C(C(C=C(O1)C(=O)O)O)OS(=O)(=O)O.[Na]
• Canonical SMILES: O=CC(C(C(C(CO)O)O)OC1OC(=CC(C1OS(=O)(=O)O)O)C(=O)O)NC(=O)C.[Na]
• InChI: InChI=1S/C14H21NO14S.Na/c1-5(18)15-6(3-16)11(10(21)8(20)4-17)28-14-12(29-30(24,25)26)7(19)2-9(27-14)13(22)23;/h2-3,6-8,10-12,14,17,19-21H,4H2,1H3,(H,15,18)(H,22,23)(H,24,25,26)
• InChIKey: FASCFNYWLAVRLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy]-4-hydroxy-3-(sulfooxy)-3,4-dihydro-2H-pyran-6-carboxylic acid sodium
• IUPAC Traditional name: 6-[(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy]-4-hydroxy-5-(sulfooxy)-5,6-dihydro-4H-pyran-2-carboxylic acid sodium
• Synonyms: α-ΔUA-2S-[1→3]-GalNAc; Chondroitin disaccharide Δdi-UA-2S sodium salt

Database IDs

• CAS Number: 149368-04-7
• MDL Number: MFCD00153942
• PubChem SID: 162227399; 24892809
• PubChem CID: 16219142

CALCULATED PROPERTIES

• Acid pKa: -1.9542692
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -9.419151
• LogD (pH = 7.4): -10.3722515
• Log P: -6.3332677
• Molar Refractivity: 91.0804 cm^3
• Polarizability: 37.367043 Å^3
• Polar Surface Area: 246.45 Å^2
• Rotatable Bonds: 11
• 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

DETAILS

Sigma Aldrich - C5820

Other Notes
ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GalNAc = N-acetyl-D-galactosamine; 2S = 2-sulfate
Application
Chondroitin, a glucosaminoglycan (GAG), is a polysaccharide chain of alternating units of N-acetylgalactosamine (GalNAc) and glucuronic acid (GlcA) that can be sulfated on the either or both GalNAc and GlcA units. Chondroitin and its sulfates are frequently attached to proteins to form proteoglycans.