2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-(prop-2-en-1-yl)-6,7,8,9-tetrahydro-1H-purine-6,8-dione

• ChemBase ID: 159684
• Molecular Formular: C13H17N5O6
• Molecular Mass: 339.30398
• Monoisotopic Mass: 339.11788329
• SMILES: C1(O)[C@@H](CO)O[C@H]([C@H]1O)n1c2nc([nH]c(=O)c2n(c1=O)CC=C)N
• Canonical SMILES: C=CCn1c(=O)n(c2c1c(=O)[nH]c(n2)N)[C@@H]1O[C@@H](C([C@@H]1O)O)CO
• InChI: InChI=1S/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7?,8+,11-/m1/s1
• InChIKey: VDCRFBBZFHHYGT-DWVWSIQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-(prop-2-en-1-yl)-6,7,8,9-tetrahydro-1H-purine-6,8-dione
• IUPAC Traditional name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-(prop-2-en-1-yl)-1H-purine-6,8-dione
• Synonyms: 7-Allyl-2-amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7,9-dihydro-1H-purine-6,8-dione, Loxoribine; 7-Allyl-7,8-dihydro-8-oxoguanosine(Loxoribine)

Database IDs

• CAS Number: 121288-39-9
• PubChem SID: 162253819
• PubChem CID: 71313091

CALCULATED PROPERTIES

• Acid pKa: 11.062581
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.084215
• LogD (pH = 7.4): -2.0795352
• Log P: -2.07939
• Molar Refractivity: 88.4635 cm^3
• Polarizability: 30.286987 Å^3
• Polar Surface Area: 160.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 227-230°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A550000

7-Allyl-7,8-dihydro-8-oxoguanosine (Loxoribine) is a small-molecule immunostimulant. Loxoribine is a toll-like receptor 7 (TLR7) agonist; induces immune cell activation and increases cytokine production. Loxoribine displays antitumor and antiviral activi

REFERENCES

• Goodman, M.G., et al.: J. Immunol., 135, 3284 (1985)
• Reitz, A. B., et al.: J. Med. Chem., 37, 3561 (1994)