(2S,4R,5S,6S)-5-acetamido-4-hydroxy-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 1541
• Molecular Formular: C21H25NO11
• Molecular Mass: 467.4233
• Monoisotopic Mass: 467.14276063
• SMILES: CC(=O)N[C@H]1[C@H](O)C[C@](O[C@@H]1[C@@H](O)[C@H](O)CO)(Oc1ccc2c(C)cc(=O)oc2c1)C(=O)O
• Canonical SMILES: OC[C@H]([C@@H]([C@H]1O[C@@](C[C@H]([C@@H]1NC(=O)C)O)(Oc1ccc2c(c1)oc(=O)cc2C)C(=O)O)O)O
• InChI: InChI=1S/C21H25NO11/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30)/t13-,14-,17+,18+,19+,21-/m1/s1
• InChIKey: KKDWIUJBUSOPGC-CJRKPKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R,5S,6S)-5-acetamido-4-hydroxy-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: @methylumbelliferyl sialic acid
• Synonyms: Methylumbelliferyl Sialic Acid

Database IDs

• PubChem SID: 160964998; 46504808
• PubChem CID: 46936209

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.814878
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.7484286
• LogD (pH = 7.4): -4.6131625
• Log P: -1.1202775
• Molar Refractivity: 107.8139 cm^3
• Polarizability: 42.96131 Å^3
• Polar Surface Area: 192.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.91
• LOG S: -2.08
• Solubility (Water): 3.88e+00 g/l

DETAILS

DrugBank - DB01768

Drug information: experimental