(2R,4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 155998
• Molecular Formular: C9H16O9
• Molecular Mass: 268.21794
• Monoisotopic Mass: 268.07943209
• SMILES: C1[C@@H]([C@H]([C@@H](O[C@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](O)(C[C@@H]([C@H]1O)O)C(=O)O)O)O
• InChI: InChI=1S/C9H16O9/c10-2-4(12)6(14)7-5(13)3(11)1-9(17,18-7)8(15)16/h3-7,10-14,17H,1-2H2,(H,15,16)/t3-,4+,5+,6+,7+,9+/m0/s1
• InChIKey: CLRLHXKNIYJWAW-LSRLBZCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 3-Deoxy-D-glycero-D-galactononulopyranosonic acid; Ketodeoxynonulosonic acid

Database IDs

• CAS Number: 153666-19-4
• MDL Number: MFCD01863086
• Beilstein Number: 5439887
• PubChem SID: 162250136; 24881944
• PubChem CID: 197508

CALCULATED PROPERTIES

• Acid pKa: 2.892075
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -5.8357577
• LogD (pH = 7.4): -6.7620726
• Log P: -3.2759023
• Molar Refractivity: 52.6801 cm^3
• Polarizability: 22.021454 Å^3
• Polar Surface Area: 167.91 Å^2
• Rotatable Bonds: 4
• 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: ≥99.0% (TLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C9H16O9

DETAILS

Sigma Aldrich - 60714

Application
Ketodeoxynonulosonic acid (KDN) is a monosaccharide of some O-linked glycan structures used as a substrate to identify, differentiate and characterize 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid hydrolase(s) (KDNase) and KDN-sialidase(s):