3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

• ChemBase ID: 53140
• Molecular Formular: C6H5N3O
• Molecular Mass: 135.1234
• Monoisotopic Mass: 135.0432618
• SMILES: [nH]1cnc2c(c1=O)cc[nH]2
• Canonical SMILES: O=c1[nH]cnc2c1cc[nH]2
• InChI: InChI=1S/C6H5N3O/c10-6-4-1-2-7-5(4)8-3-9-6/h1-3H,(H2,7,8,9,10)
• InChIKey: FBMZEITWVNHWJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• IUPAC Traditional name: 3H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• Synonyms: 3H-Pyrrolo[2,3-d]pyrimidin-4(7H)-one; 7-Deaza-6-hydroxy Purine; NSC 124164; NSC 59251; 7-Deazahypoxanthine; 3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one; 3,7-Dihydro-4-oxo-4H-pyrrolo[2,3-d]pyrimidine; 3,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 95+%; 3,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one; 7-Deazahypoxanthine

Database IDs

• CAS Number: 3680-71-5
• MDL Number: MFCD01686814; MFCD08234923
• PubChem SID: 162057903
• PubChem CID: 96194

CALCULATED PROPERTIES

• Acid pKa: 9.894313
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.11461386
• LogD (pH = 7.4): -0.10671336
• Log P: -0.10608309
• Molar Refractivity: 36.9115 cm^3
• Polarizability: 12.747434 Å^3
• Polar Surface Area: 57.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Colourless Crystalline Solid
• Melting Point: 345-348°C; 345-350 °C
• Hydrophobicity(logP): -0.444

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Harmful/Irritant/Keep Cold; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C6H5N3O

DETAILS

Sigma Aldrich - 731935

Packaging
1 g in glass bottle

Toronto Research Chemicals - D201600

Xanthine oxidase-activated prodrug of thymidine phosphorylase inhibitor

REFERENCES

• Reigan, P., et al.: Bioorg. Med. Chem. Lett., 14, 5247 (2004)
• Lahoud, G., et al.: Nucleic Acids Res., 36, 6999 (2004)
• Reigan, P., et al.: Eur. J. Med. Chem., 43, 1248 (2004)