disodium (3R,4S)-2-{[(3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-[(sulfonatooxy)methyl]oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 132484
• Molecular Formular: C14H19NNa2O14S
• Molecular Mass: 503.3435
• Monoisotopic Mass: 503.03216386
• SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](OC1O)COS(=O)(=O)[O-])O)OC1[C@@H]([C@H](C=C(O1)C(=O)[O-])O)O.[Na+].[Na+]
• Canonical SMILES: CC(=O)N[C@H]1C(O)O[C@@H]([C@@H]([C@@H]1OC1OC(=C[C@@H]([C@H]1O)O)C(=O)[O-])O)COS(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C14H21NO14S.2Na/c1-4(16)15-8-11(10(19)7(27-13(8)22)3-26-30(23,24)25)29-14-9(18)5(17)2-6(28-14)12(20)21;;/h2,5,7-11,13-14,17-19,22H,3H2,1H3,(H,15,16)(H,20,21)(H,23,24,25);;/q;2*+1/p-2/t5-,7+,8+,9+,10-,11+,13?,14?;;/m0../s1
• InChIKey: JLCMHASLMZGEFC-KHMUHUMZSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (3R,4S)-2-{[(3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-[(sulfonatooxy)methyl]oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: disodium (4S,5R)-6-{[(3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-[(sulfonatooxy)methyl]oxan-4-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: α-ΔUA-[1→3]-GalNAc-6S; Chondroitin disaccharide Δdi-6S sodium salt

Database IDs

• CAS Number: 136132-72-4
• MDL Number: MFCD00133171
• PubChem SID: 24892672; 162226761
• PubChem CID: 71308565

CALCULATED PROPERTIES

• Acid pKa: -2.0367377
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -8.559274
• LogD (pH = 7.4): -9.704272
• Log P: -5.8039627
• Molar Refractivity: 99.3736 cm^3
• Polarizability: 37.034477 Å^3
• Polar Surface Area: 244.27 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

DETAILS

Sigma Aldrich - C4170

Other Notes
ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GalNAc = N-acetyl-D-galactosamine; 6S = 6-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.