4-amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 154451
• Molecular Formular: C9H12FN3O4
• Molecular Mass: 245.2076832
• Monoisotopic Mass: 245.0811841
• SMILES: c1c(c(nc(=O)n1[C@H]1C[C@@H]([C@H](O1)CO)O)N)F
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(F)c(nc1=O)N
• InChI: InChI=1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
• InChIKey: IDYKCXHJJGMAEV-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 5-fluoro-2'-deoxycytidine
• Synonyms: 2′-deoxy-5-fluoro-Cytidine; FCDR; FdCyd; 5-Fluoro-2′-deoxycytidine

Database IDs

• CAS Number: 10356-76-0
• MDL Number: MFCD00077348
• PubChem SID: 162248590
• PubChem CID: 515328

CALCULATED PROPERTIES

• Acid pKa: 13.894899
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.6974363
• LogD (pH = 7.4): -1.6974365
• Log P: -1.6974363
• Molar Refractivity: 53.237 cm^3
• Polarizability: 20.655432 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H12FN3O4

DETAILS

Sigma Aldrich - F5307

Biochem/physiol Actions
5-Fluoro-2′-deoxycytidine is a mechanism based DNMT (DNA cytosine-5 methyltransferase) inhibitor, that forms a covalent link with the cysteine residue in the active site of DNMT.