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

• ChemBase ID: 4247
• Molecular Formular: C9H15FO8
• Molecular Mass: 270.2090032
• Monoisotopic Mass: 270.07509566
• SMILES: OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@H]([C@H](F)[C@H](O)[C@H]1O)C(=O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@H](C(=O)O)[C@@H]([C@@H]([C@H]1O)O)F)O)O
• InChI: InChI=1S/C9H15FO8/c10-3-5(14)6(15)8(4(13)2(12)1-11)18-7(3)9(16)17/h2-8,11-15H,1H2,(H,16,17)/t2-,3-,4-,5+,6-,7+,8+/m1/s1
• InChIKey: LYONSLFAVFDWPW-KVCYNOHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 2-keto-3-deoxy-d-glycero-d-galacto-3-fluoronononic acid; 2,6-anhydro-3-deoxy-3-fluoro-l-arabino-d-galacto-nononic acid; 2,6-anhydro-3-deoxy-3-fluoronononic acid

Database IDs

• PubChem SID: 46505654; 160967679
• PubChem CID: 5459366

CALCULATED PROPERTIES

JChem

• H Donor: 6
• LogD (pH = 5.5): -5.174808
• LogD (pH = 7.4): -6.6021194
• Log P: -3.247954
• Molar Refractivity: 50.9563 cm^3
• Polarizability: 21.214157 Å^3
• Polar Surface Area: 147.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false
• Acid pKa: 3.567335
• H Acceptors: 8

ALOGPS 2.1

• Log P: -1.98
• LOG S: -0.26
• Solubility (Water): 1.48e+02 g/l

DETAILS

DrugBank - DB04694

Drug information: experimental