Standard InChI: InChI=1S/C18H22N4O4/c1-4-8-21-16-14(17(24)22(9-5-2)18(21)25)19-15(20-16)12-7-6-11(26-3)10-13(12)23/h6-7,10,23H,4-5,8-9H2,1-3H3,(H,19,20)
Standard InChI Key: RQAXETYXJICKOZ-UHFFFAOYSA-N
Associated Targets(Human)
Adenosine A2b receptor 7672 Activities
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Adenosine A2 receptor 1064 Activities
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Associated Targets(non-human)
Adenosine A1 receptor 6163 Activities
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Adenosine A2a receptor 3360 Activities
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Adenosine A2 receptor 1828 Activities
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Adenosine receptors; A1 & A2 886 Activities
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Molecule Features
Natural Product: No
Oral: No
Chemical Probe: No
Parenteral: No
Molecule Type: Small molecule
Topical: No
First In Class: No
Black Box: No
Chirality: No
Availability: No
Prodrug: No
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Properties
Molecular Weight: 358.40
Molecular Weight (Monoisotopic): 358.1641
AlogP: 2.09
#Rotatable Bonds: 6
Polar Surface Area: 102.14
Molecular Species: NEUTRAL
HBA: 7
HBD: 2
#RO5 Violations: 0
HBA (Lipinski): 8
HBD (Lipinski): 2
#RO5 Violations (Lipinski): 0
CX Acidic pKa: 6.90
CX Basic pKa:
CX LogP: 2.55
CX LogD: 2.06
Aromatic Rings: 3
Heavy Atoms: 26
QED Weighted: 0.70
Np Likeness Score: -0.63
References
1.Daly JW, Padgett WL, Shamim MT.. (1986) Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents., 29 (8):[PMID:3016270][10.1021/jm00158a034]
2.Kim SA, Marshall MA, Melman N, Kim HS, Müller 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., 45 (11):[PMID:12014951][10.1021/jm0104318]
3.Shamim MT, Ukena D, Padgett WL, Hong O, Daly JW.. (1988) 8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors., 31 (3):[PMID:3346878][10.1021/jm00398a020]
4.Bansal R, Kumar G, Gandhi D, Young LC, Harvey AL.. (2009) Synthesis of a series of 8-(substituted-phenyl)xanthines and a study on the effects of substitution pattern of phenyl substituents on affinity for adenosine A(1) and A(2A) receptors., 44 (5):[PMID:19036477][10.1016/j.ejmech.2008.10.017]
