4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzoic acid

ID: ALA423239

Chembl Id: CHEMBL423239

Cas Number: 94781-78-9

PubChem CID: 122071

Max Phase: Preclinical

Molecular Formula: C18H20N4O4

Molecular Weight: 356.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(-c3ccc(C(=O)O)cc3)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C18H20N4O4/c1-3-9-21-15-13(16(23)22(10-4-2)18(21)26)19-14(20-15)11-5-7-12(8-6-11)17(24)25/h5-8H,3-4,9-10H2,1-2H3,(H,19,20)(H,24,25)

Standard InChI Key:  DNQSBNFCLWHHHQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA423239

   Benzoic acid, 4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)-

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: 356.38

Molecular Weight (Monoisotopic): 356.1485

AlogP: 2.07

#Rotatable Bonds: 6

Polar Surface Area: 109.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.90

CX Basic pKa: 1.65

CX LogP: 2.63

CX LogD: -0.72

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.79

References

1. Shamim MT, Ukena D, Padgett WL, Daly JW..  (1989)  Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.,  32  (6): [PMID:2724296] [10.1021/jm00126a014]

2. 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]

3. Kim HO, Ji XD, Melman N, Olah ME, Stiles GL, Jacobson KA..  (1994)  Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.,  37  (20): [PMID:7932565] [10.1021/jm00046a022]

4. 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.,  28  (4): [PMID:2984420] [10.1021/jm00382a018]

5. 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]

Source

Source(1):

• Scientific Literature