1-[5-hydroxy(4,4,5,6,6,6-2H6)hexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 172355
• Molecular Formular: C13H20N4O3
• Molecular Mass: 280.3229
• Monoisotopic Mass: 280.15354052
• SMILES: n1(c(=O)n(c2c(c1=O)n(cn2)C)C)CCCCC(O)C
• Canonical SMILES: CC(CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
• InChI: InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3
• InChIKey: NSMXQKNUPPXBRG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[5-hydroxy(4,4,5,6,6,6-^2H₆)hexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 1-[5-hydroxy(4,4,5,6,6,6-^2H₆)hexyl]-3,7-dimethylpurine-2,6-dione
• Synonyms: 3,7-Dihydro-1-(5-hydroxyhexyl-d6)-3,7-dimethyl-1H-purine-2,6-dione; 1-(5-Hydroxyhexyl-d6)theobromine; (+/-)-1-(5-Hydroxyhexyl-d6)-3,7-dimethylxanthine; BL 194-d6; Pentoxifylline-d6 Alcohol; (+/-)-Lisofylline-d6

Database IDs

• PubChem SID: 164228265
• PubChem CID: 44208375

CALCULATED PROPERTIES

• Acid pKa: 17.683033
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.20271832
• LogD (pH = 7.4): 0.2027185
• Log P: 0.2027185
• Molar Refractivity: 74.6533 cm^3
• Polarizability: 27.659185 Å^3
• Polar Surface Area: 78.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469053

A major oxidative labelled metabolite of Pentoxifylline. A potent inhibitor of phosphatidic acid generation (IC50=0.6uM). Protects mice from endotoxic shock and attenuates sepsis-induced acute lung injury in pig.

REFERENCES

• Clarke, E., et al.: Cancer Res., et al.: 56, 105 (1996)
• Itani, S., et al.: Metabolism, 50, 553 (1996)
• Itani, S., et al.: Diabetes, 51, 2005(1996)
• Yu, C., et al.: J. Biol. Chem., 277, 50230 (1996)