8-(4-hydroxyphenyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 179888
• Molecular Formular: C13H12N4O3
• Molecular Mass: 272.25938
• Monoisotopic Mass: 272.09094026
• SMILES: c12c(c(=O)n(c(=O)n1C)C)[nH]c(n2)c1ccc(cc1)O
• Canonical SMILES: Oc1ccc(cc1)c1[nH]c2c(n1)n(C)c(=O)n(c2=O)C
• InChI: InChI=1S/C13H12N4O3/c1-16-11-9(12(19)17(2)13(16)20)14-10(15-11)7-3-5-8(18)6-4-7/h3-6,18H,1-2H3,(H,14,15)
• InChIKey: YGBHMJNRSBKDLF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(4-hydroxyphenyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-(4-hydroxyphenyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Synonyms: NPC-189

Database IDs

• CAS Number: 85872-69-1
• PubChem SID: 164235798
• PubChem CID: 5422370

CALCULATED PROPERTIES

• Acid pKa: 7.244841
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.94508934
• LogD (pH = 7.4): 0.6351479
• Log P: 0.95188326
• Molar Refractivity: 82.017 cm^3
• Polarizability: 26.89812 Å^3
• Polar Surface Area: 89.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Adenosine A1, A2 receptor antagonist; Purine antagonist

Product Information

• Description: Isomers
• Application(s): Cytostatic

REFERENCES

• 1. Hamilton HW,Ortwine DF,Worth DF,Badger EW,Bristol JA,Bruns RF,Haleen SJ,Steffen RP (1985)
• Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application. Journal of medicinal chemistry 28, 1071-9
• 2. Jacobson KA,Kirk KL,Padgett WL,Daly JW (1985) Functionalized congeners of 1,3-dialkylxanthines: preparation of analogues with high affinity for adenosine receptors.
• Journal of medicinal chemistry 28, 1334-40
• 3. Daly JW,Padgett W,Shamim MT,Butts-Lamb P,Waters J (1985) 1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
• Journal of medicinal chemistry 28, 487-92
• 4. Kim SA,Marshall MA,Melman N,Kim HS,Muller CE,Linden J,Jacobson KA (2002)
• Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions. Journal of medicinal chemistry 45, 2131-8