5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride

• ChemBase ID: 160537
• Molecular Formular: C9H14ClN3O6
• Molecular Mass: 295.67696
• Monoisotopic Mass: 295.05711286
• SMILES: Cl.[C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)N)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cc(N)c(=O)[nH]c1=O.Cl
• InChI: InChI=1S/C9H13N3O6.ClH/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8;/h1,4-6,8,13-15H,2,10H2,(H,11,16,17);1H/t4-,5+,6?,8-;/m1./s1
• InChIKey: FPVJCMJKVVJWAA-RMQALDHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• IUPAC Traditional name: 5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione hydrochloride
• Synonyms: 5-Aminouridine Hydrochloride; 5-Amino Uridine Hydrochloride

Database IDs

• CAS Number: 116154-74-6
• PubChem SID: 162254672
• PubChem CID: 46780367

CALCULATED PROPERTIES

• Acid pKa: 9.471011
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.2992933
• LogD (pH = 7.4): -3.3028777
• Log P: -3.2992475
• Molar Refractivity: 56.1905 cm^3
• Polarizability: 22.07473 Å^3
• Polar Surface Area: 145.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >210°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A632125

Has a wide range of biological effects including inhibiting the growth of bacteria, fungi, viruses, protozoa, and tumors.

REFERENCES

• Roberts, M. and Visser, D.W.: J. Biol. Chem., 194, 695 (1952)
• Beltz, R.E., et al.: J. Biol. Chem., 226, 1035 (1952)