3-fluoro-6-(hydroxymethyl)oxane-2,4,5-triol

• ChemBase ID: 133232
• Molecular Formular: C6H11FO5
• Molecular Mass: 182.1469432
• Monoisotopic Mass: 182.05905167
• SMILES: C(C1C(C(C(C(O1)O)F)O)O)O
• Canonical SMILES: OCC1OC(O)C(C(C1O)O)F
• InChI: InChI=1S/C6H11FO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1H2
• InChIKey: ZCXUVYAZINUVJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-fluoro-6-(hydroxymethyl)oxane-2,4,5-triol
• IUPAC Traditional name: 2-deoxy-2-fluorohexopyranose
• Synonyms: 2-Deoxy-2-fluoro-D-glucose; FDG; 2-Fluoro-2-deoxy-D-glucose

Database IDs

• CAS Number: 29702-43-0
• MDL Number: MFCD00077527
• PubChem SID: 162227509; 24894876
• PubChem CID: 315411

CALCULATED PROPERTIES

• Acid pKa: 11.021989
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.0414488
• LogD (pH = 7.4): -2.041551
• Log P: -2.0414474
• Molar Refractivity: 34.2313 cm^3
• Polarizability: 14.345064 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - F5006

Biochem/physiol Actions
Glucose analog that inhibits cellular glycosylation. Natural isotope-form of 18F-FDG that can be taken up by cells but does not undergo metabolic glycolysis.