{[(2R,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 164092
• Molecular Formular: C10H13ClN5O7P
• Molecular Mass: 381.666281
• Monoisotopic Mass: 381.02411209
• SMILES: c12c(nc(nc1N)Cl)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1nc(Cl)nc2N)COP(=O)(O)O
• InChI: InChI=1S/C10H13ClN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6-,9-/m1/s1
• InChIKey: FXXRIUZMLRLFKP-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2-Chloro-5'-adenylic Acid; 2-Chloro-adenosine 5'-(Dihydrogen Phosphate) Ditriethylamine; 2-Chloro-AMP Ditriethylamine; 2-Chloroadenosine 5'-Monophosphate Ditriethylamine Salt

Database IDs

• PubChem SID: 162258227
• PubChem CID: 9951889

CALCULATED PROPERTIES

• Acid pKa: 1.3363523
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.7476285
• LogD (pH = 7.4): -4.836514
• Log P: -1.6573179
• Molar Refractivity: 79.5671 cm^3
• Polarizability: 31.194397 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >95°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C364100

A metabolite of 2-Chloroadenosine; an adenine nucleotide receptor.

REFERENCES

• Chung, T., et al.: J. Biol. Chem., 272, 3064 (1997)
• Fredholm, B., et al.: Pharmacol. Rev., 53, 527 (1997)
• Ryten, M., et al.: J. Cell. Biol., 158, 345 (1997)
• Schrier, S., et al.: Biochem. Pharmacol., 63, 1119 (1997)