2-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

• ChemBase ID: 3951
• Molecular Formular: C6H6N4O
• Molecular Mass: 150.13804
• Monoisotopic Mass: 150.05416083
• SMILES: Nc1nc2cc[nH]c2c(=O)[nH]1
• Canonical SMILES: Nc1nc2cc[nH]c2c(=O)[nH]1
• InChI: InChI=1S/C6H6N4O/c7-6-9-3-1-2-8-4(3)5(11)10-6/h1-2,8H,(H3,7,9,10,11)
• InChIKey: FFYPRJYSJODFFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one; 2-aminopyrrolo[3,2-d]pyrimidin-4-one
• IUPAC Traditional name: 2-amino-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one; 2-aminopyrrolo[3,2-d]pyrimidin-4-one
• Synonyms: 2-Amino-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; NSC 344522; 9-Deazaguanine

Database IDs

• CAS Number: 65996-58-9
• PubChem SID: 46508363; 160967386
• PubChem CID: 23644492; 100684

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.182469
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.92188877
• LogD (pH = 7.4): -0.5100002
• Log P: -0.5030531
• Molar Refractivity: 40.825 cm^3
• Polarizability: 13.9076395 Å^3
• Polar Surface Area: 83.27 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.97
• LOG S: -1.07
• Solubility (Water): 1.28e+01 g/l

PROPERTIES

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB04356

Drug information: experimental

Toronto Research Chemicals - D201330

A nucleoside analog as potent inhibitor of purine nucleoside phosphorylase.

REFERENCES

• Erion, M.D., et al.: J. Med. Chem., 36, 3771 (1993)
• Seela, F., et al.: Org. Biomol. Chem., 4, 3993 (1993)
• Hikishima S., et al.: Bioorg. Med. Chem. Lett., 17, 4173 (1993)