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

• ChemBase ID: 132536
• Molecular Formular: C14H21NNaO11
• Molecular Mass: 402.30641
• Monoisotopic Mass: 402.10122978
• SMILES: CC(=O)NC(C=O)C(C(C(CO)O)O)OC1C(C(C=C(O1)C(=O)O)O)O.[Na]
• Canonical SMILES: O=CC(C(C(C(CO)O)O)OC1OC(=CC(C1O)O)C(=O)O)NC(=O)C.[Na]
• InChI: InChI=1S/C14H21NO11.Na/c1-5(18)15-6(3-16)12(10(21)8(20)4-17)26-14-11(22)7(19)2-9(25-14)13(23)24;/h2-3,6-8,10-12,14,17,19-22H,4H2,1H3,(H,15,18)(H,23,24)
• InChIKey: ZIEOMBVLIDBWRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy]-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid sodium
• IUPAC Traditional name: 6-[(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy]-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid sodium
• Synonyms: α-ΔUA-(1→3)-GlcNAc; Hyaluronic acid disaccharide ΔDiHA sodium salt; α-ΔUA-[1→3]-GalNAc; Chondroitin disaccharide Δdi-0S sodium salt

Database IDs

• CAS Number: 136132-69-9; 149368-06-9
• MDL Number: MFCD00166873; MFCD00133173
• PubChem SID: 24892657; 162226813; 24895867
• PubChem CID: 16219116

CALCULATED PROPERTIES

• Acid pKa: 3.18169
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -6.862502
• LogD (pH = 7.4): -8.016677
• Log P: -4.568028
• Molar Refractivity: 81.0886 cm^3
• Polarizability: 32.36584 Å^3
• Polar Surface Area: 203.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥85%

DETAILS

Sigma Aldrich - C3920

Other Notes
ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GalNAc = N-acetyl-D-galactosamine
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.

Sigma Aldrich - H9649

Other Notes
ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GlcNAc = N-acetyl-D-glucosamine
Preparation Note
Product of digestion of hyaluronic acid by chondroitinase.