6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2H-purin-2-one

• ChemBase ID: 179883
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: c12n([C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)cnc1c(nc(=O)[nH]2)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1[nH]c(=O)nc2N
• InChI: InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
• InChIKey: MIKUYHXYGGJMLM-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2H-purin-2-one
• IUPAC Traditional name: 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2H-purin-2-one
• Synonyms: 9-beta- D -Ribofuranosylisoguanine; Crotonoside; 2-Hydroxyadenosine; 6-Amino-9-beta- D -ribofuranosyl-9 H -purin-2(1 H )-one; Isoguanosine

Database IDs

• CAS Number: 1818-71-9
• PubChem SID: 164235793
• PubChem CID: 65085

CALCULATED PROPERTIES

• Acid pKa: 10.857788
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.8389428
• LogD (pH = 7.4): -2.8387556
• Log P: -2.8386073
• Molar Refractivity: 64.1877 cm^3
• Polarizability: 24.512907 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Antioxidant; Glutamic acid dehydrogenase inhibitor; Inosine monophosphate pyrophosphonylase inhibitor; Stimulates cyclic AMP incorporation into brain tissue

Product Information

• Description: Tautomers
• Biological Source: Occurs in the seeds of Croton tiglium . Also isol. from the nudibranch Diaulula sandiegensis
• Application(s): Antioxidant; Regulates brain disorders,

REFERENCES

• Cherbuliez, E. et al., Helv. Chim. Acta, 1932, 15, 464; 978, (isol)
• Spies, J.R., J.A.C.S., 1939, 61, 350, (occur)
• Davoll, J., J.A.C.S., 1951, 73, 3174, (synth, isol)
• Yamazaki, A. et al., Chem. Pharm. Bull., 1968, 16, 2172, (synth)
• Miura, K. et al., Chem. Pharm. Bull., 1975, 23, 2064, (synth)
• Sepiol, J. et al., Z. Naturforsch., C, 1976, 37, 361, (uv)
• Fuhrmann, F.A. et al., Science (Washington, D.C.), 1981, 212, 557, (isol)
• Nair, V. et al., J.O.C., 1985, 50, 406, (synth, pmr)
• Divakar, K.J. et al., J.C.S. Perkin 1, 1991, 771, (synth, uv, pmr, cmr)
• Chern, J.-W. et al., J.O.C., 1991, 56, 4213, (synth)
• De Napoli, L. et al., J.C.S. Perkin 1, 1995, 15, (synth, bibl)