5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 3219
• Molecular Formular: C4H3IN2O2
• Molecular Mass: 237.98329
• Monoisotopic Mass: 237.92392535
• SMILES: Ic1c[nH]c(=O)[nH]c1=O
• Canonical SMILES: Ic1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChIKey: KSNXJLQDQOIRIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-iodouracil
• Synonyms: 5-Iodouracil; 2,4-Dihydroxy-5-iodopyrimidine; 5-Iodouracil; 5-Iodouracil 97%; 5-Iodo-2,4(1H,3H)-pyrimidinedione; 5-Iodo-2,4-dihydroxypyrimidine; 5-Iodo-2,4-pyrimidinedione; 5-Iodopyrimidine-2,4-diol; 5-Iodouracil; NSC 57848; 2,4-二羟基-5-碘嘧啶; 5-碘尿嘧啶

Database IDs

• CAS Number: 696-07-1
• EC Number: 211-788-2
• MDL Number: MFCD00006020
• PubChem SID: 46507512; 160966662; 24888454
• PubChem CID: 69672

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.14125
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.12941484
• LogD (pH = 7.4): 0.05887728
• Log P: 0.13039446
• Molar Refractivity: 39.3183 cm^3
• Polarizability: 15.087186 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.07
• LOG S: -1.47
• Solubility (Water): 8.12e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 274-276 °C (dec.)(lit.); 274-276(dec.)°C

Safety Information

• Storage Warning: Irritant/Carcinogenic/Light Sensitive
• RTECS: YR0525000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-20/21/22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C4H3IN2O2

DETAILS

DrugBank - DB03554

Drug information: experimental

Sigma Aldrich - 857858

Packaging
10, 50 g in poly bottle

Toronto Research Chemicals - I728900

5-Iodouracil is a halogenated pyrimidine that can be used in nucleoprotein photo-crosslinking via RNA substitution. 5-Iodouracil is used in thymidine phosphorylase targeted imaging and therapy. Studies show that DNA N-glycosylase MED1 exhibited higher pre

REFERENCES

• Meisenheimer, K. et al.: Meth. Enzymol., 318, 88 (2000)
• Klecker, R.W. Jr. et al.: Cancer Chemother. Pharmacol., 48, 407 (2000)
• Turner, D.P. et al.: Cancer Res., 66, 7686 (2000)