4-hydroxy-2-sulfanylpyrimidine-5-carboxylic acid

• ChemBase ID: 155142
• Molecular Formular: C5H4N2O3S
• Molecular Mass: 172.16186
• Monoisotopic Mass: 171.994263
• SMILES: c1c(c(nc(n1)S)O)C(=O)O
• Canonical SMILES: Sc1ncc(c(n1)O)C(=O)O
• InChI: InChI=1S/C5H4N2O3S/c8-3-2(4(9)10)1-6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
• InChIKey: XKHWTDCFQVKNHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2-sulfanylpyrimidine-5-carboxylic acid
• IUPAC Traditional name: 4-hydroxy-2-sulfanylpyrimidine-5-carboxylic acid
• Synonyms: 2-Thiouracil-5-carboxylic acid; 5-Carboxy-4-hydroxy-2-thiopyrimidine; 5-Carboxy-2-thiouracil

Database IDs

• CAS Number: 23945-50-8
• EC Number: 245-948-8
• MDL Number: MFCD00038020
• PubChem SID: 162249280; 24893151
• PubChem CID: 3002041

CALCULATED PROPERTIES

• Acid pKa: 3.5735986
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.5008759
• LogD (pH = 7.4): -1.949578
• Log P: 1.4202038
• Molar Refractivity: 40.2287 cm^3
• Polarizability: 14.730824 Å^3
• Polar Surface Area: 83.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C5H4N2O3S

DETAILS

Sigma Aldrich - C9375

Application
5-Carboxy-2-thiouracil in metal complexes with Mn(ll), Co(ll), Ni(ll), Cu(ll), Zn(ll) and Cd(ll) ions may be useful in some anti-tumor applications. 5-Carboxy-2-thiouracil may be used to produce potential anti-bacterial and anti-tumor methylhydrazonium salts.