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HIT103094277
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HIT103094277
  • HIT ID:HIT103094277
  • Cas No:696-07-1
  • Common Name:5-Iodouracil
  • IUPAC:5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
    IUPAC:5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • InChIKey:KSNXJLQDQOIRIP-UHFFFAOYSA-N
  • Molecular Formula:C4H3IN2O2
  • Molecular Weight:237.984
  • Hydrogen Bond Donor (HBD):2
  • Hydrogen Bond Acceptor (HBA):4
  • LogP:0.403
  • SMILES:Ic1c[nH]c(=O)[nH]c1=O
    SMILES:Ic1c[nH]c(=O)[nH]c1=O
  • 5-Iodouracil is a halogenated pyrimidine analog that functions as a potent mechanism-based inactivator of dihydropyrimidine dehydrogenase (DHPDHase), the rate-limiting enzyme in pyrimidine degradation. The compound achieves a complete titration of enzymatic activity at a stoichiometry of 1.7 moles per mole of enzyme-bound flavin, with a partition coefficient of 4.5 for inactivation. Its binding triggers a conformational change in a flexible active-site loop, positioning a catalytic cysteine residue for covalent modification and forming a S-(hexahydro-2,4-dioxo-5-pyrimidinyl) cysteine adduct. This compound is widely used in crystallographic studies of electron transfer chains spanning 56 Å across multiple cofactors, and serves as a valuable tool for probing pyrimidine metabolism and designing photo-responsive oligonucleotide systems.
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