8-(2-Hydroxy-4-methoxy-phenyl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

ID: ALA350469

Chembl Id: CHEMBL350469

PubChem CID: 136044105

Max Phase: Preclinical

Molecular Formula: C18H22N4O4

Molecular Weight: 358.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2[nH]c(-c3ccc(OC)cc3O)nc2n(CCC)c1=O

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

Alternative Forms

1. Parent:

   

   ALA350469

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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

Calculated 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]

Source

Source(1):

• Scientific Literature