{4-[(2,5-diamino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol

• ChemBase ID: 166798
• Molecular Formular: C10H14ClN5O
• Molecular Mass: 255.70406
• Monoisotopic Mass: 255.08868777
• SMILES: C1=CC(CC1Nc1nc(nc(c1N)Cl)N)CO
• Canonical SMILES: OCC1C=CC(C1)Nc1nc(N)nc(c1N)Cl
• InChI: InChI=1S/C10H14ClN5O/c11-8-7(12)9(16-10(13)15-8)14-6-2-1-5(3-6)4-17/h1-2,5-6,17H,3-4,12H2,(H3,13,14,15,16)
• InChIKey: RNURTQFRFNOOPJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(2,5-diamino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol
• IUPAC Traditional name: {4-[(2,5-diamino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol
• Synonyms: (1S-cis)-4-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol; (1S,4R)-4-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol; (1S-cis)-(+/-)-4-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol; (1S,4R)-rel-4-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol

Database IDs

• CAS Number: 896716-96-4; 141271-11-6
• PubChem SID: 162260931
• PubChem CID: 9816528

CALCULATED PROPERTIES

• Acid pKa: 15.430291
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.10075952
• LogD (pH = 7.4): 0.037028175
• Log P: 0.03910896
• Molar Refractivity: 72.2186 cm^3
• Polarizability: 24.676931 Å^3
• Polar Surface Area: 110.08 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D416246

Carbovir intermediate.

Toronto Research Chemicals - D416245

Abacavir (A105000) impurity.

REFERENCES

• Vince, R., et al.: J. Med. Chem., 33, 17 (1990)
• Harnden, M., et al.: J. Med. Chem., 33, 187 (1990)
• Foster, R., et al.: Drugs, 55, 729 (1990)