3-{3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]propanoyl}benzoic acid

• ChemBase ID: 169528
• Molecular Formular: C19H18N4O7
• Molecular Mass: 414.36882
• Monoisotopic Mass: 414.11754894
• SMILES: [nH]1cnc2c(c1=O)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CCC(=O)c1cc(ccc1)C(=O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](CCC(=O)c2cccc(c2)C(=O)O)O[C@H]([C@@H]1O)n1cnc2c1nc[nH]c2=O
• InChI: InChI=1S/C19H18N4O7/c24-11(9-2-1-3-10(6-9)19(28)29)4-5-12-14(25)15(26)18(30-12)23-8-22-13-16(23)20-7-21-17(13)27/h1-3,6-8,12,14-15,18,25-26H,4-5H2,(H,28,29)(H,20,21,27)/t12-,14-,15-,18-/m1/s1
• InChIKey: VEDWXCWBMDQNCV-SCFUHWHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]propanoyl}benzoic acid
• IUPAC Traditional name: futalosine
• Synonyms: Futalosine; 3-[1,5,6-Trideoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)-β-D-ribo-heptofuranuronoyl]benzoic Acid

Database IDs

• CAS Number: 210644-32-9
• PubChem SID: 162263660
• PubChem CID: 10364451

CALCULATED PROPERTIES

• Acid pKa: 3.9135375
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.9659435
• LogD (pH = 7.4): -3.5906794
• Log P: -0.3729568
• Molar Refractivity: 101.6518 cm^3
• Polarizability: 38.12586 Å^3
• Polar Surface Area: 163.34 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F866500

A new nucleoside analog, was isolated from a fermentation broth of Streptomyces sp. MK359-NF1. An antibiotic cancer inhibitor.

REFERENCES

• Parkin, D., et al.: J. Biol. Chem., 271, 21713 (1996)
• Meganathan, R., et al.: Vitam. Horm., 61, 173 (1996)
• Hiratsuka, T., et al.: Science, 321, 1670 (1996)