(2R,4R,5S,6S)-5-acetamido-4-hydroxy-2-(prop-2-en-1-yl)-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 1490
• Molecular Formular: C14H23NO8
• Molecular Mass: 333.33432
• Monoisotopic Mass: 333.1423667
• SMILES: CC(=O)N[C@H]1[C@H](O)C[C@@](CC=C)(O[C@@H]1[C@@H](O)[C@H](O)CO)C(=O)O
• Canonical SMILES: C=CC[C@@]1(C[C@@H](O)[C@@H]([C@H](O1)[C@H]([C@@H](CO)O)O)NC(=O)C)C(=O)O
• InChI: InChI=1S/C14H23NO8/c1-3-4-14(13(21)22)5-8(18)10(15-7(2)17)12(23-14)11(20)9(19)6-16/h3,8-12,16,18-20H,1,4-6H2,2H3,(H,15,17)(H,21,22)/t8-,9-,10+,11+,12+,14-/m1/s1
• InChIKey: IUGVDRFIVSPVGO-VEWLJJDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5S,6S)-5-acetamido-4-hydroxy-2-(prop-2-en-1-yl)-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4R,5S,6S)-5-acetamido-4-hydroxy-2-(prop-2-en-1-yl)-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 2-Propenyl-N-Acetyl-Neuramic Acid

Database IDs

• PubChem SID: 46505271; 160964949
• PubChem CID: 46936198

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6834655
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.4557285
• LogD (pH = 7.4): -5.952991
• Log P: -2.640917
• Molar Refractivity: 76.535 cm^3
• Polarizability: 30.707531 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.77
• LOG S: -0.64
• Solubility (Water): 7.68e+01 g/l

DETAILS

DrugBank - DB01716

Drug information: experimental