6-amino-1,2-dihydropyrimidine-2-thione

• ChemBase ID: 160227
• Molecular Formular: C4H5N3S
• Molecular Mass: 127.1676
• Monoisotopic Mass: 127.02041818
• SMILES: [nH]1c(=S)nccc1N
• Canonical SMILES: Nc1ccnc(=S)[nH]1
• InChI: InChI=1S/C4H5N3S/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
• InChIKey: DCPSTSVLRXOYGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-1,2-dihydropyrimidine-2-thione
• IUPAC Traditional name: 4-amino-3H-pyrimidine-2-thione
• Synonyms: 2-Thiocytosine; 6-Amino-2-pyrimidinethione; 4-Aminothio-2-pyrimidinone; 4-Amino-2-mercaptopyrimidine

Database IDs

• CAS Number: 333-49-3
• PubChem SID: 162254362
• PubChem CID: 2724245

CALCULATED PROPERTIES

• Acid pKa: 9.21085
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.28669134
• LogD (pH = 7.4): -0.2642688
• Log P: -0.2577362
• Molar Refractivity: 46.0057 cm^3
• Polarizability: 13.578292 Å^3
• Polar Surface Area: 50.41 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Pale Yellow to Light Orange Solid
• Melting Point: 273-277°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A611930

This compound has been shown to inhibit iodothyronine 5’-deiodinase, the enzyme responsible for the 5’-deiodination of thyroxine in human liver cells.

REFERENCES

• Harbottle, R., et al.: Biochem. J., 217, 485 (1984)