8-Bicyclo[2.2.1]hept-2-ylmethyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

ID: ALA2373406

Max Phase: Preclinical

Molecular Formula: C19H28N4O2

Molecular Weight: 344.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(C[C@H]3CC4CCC3C4)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C19H28N4O2/c1-3-7-22-17-16(18(24)23(8-4-2)19(22)25)20-15(21-17)11-14-10-12-5-6-13(14)9-12/h12-14H,3-11H2,1-2H3,(H,20,21)/t12?,13?,14-/m1/s1

Standard InChI Key:  HQRJBFICGQWZHQ-JXQTWKCFSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    5.0542   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -4.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -2.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -4.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -2.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -1.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7750   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3167   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -5.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  1  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  7  1  0
 10 11  1  1
 11  9  1  0
 12  5  2  0
 10 13  1  0
 14  6  2  0
 15 10  1  0
 16 13  1  0
 17 15  1  0
 18  3  1  0
 19  4  1  0
 20 13  1  0
 21 17  1  0
 22 18  1  0
 23 19  1  0
 24 23  1  0
 25 22  1  0
  8  9  2  0
  6  4  1  0
 17 16  1  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2373406

   ---

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: 344.46

Molecular Weight (Monoisotopic): 344.2212

AlogP: 2.69

#Rotatable Bonds: 6

Polar Surface Area: 72.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.69

CX Basic pKa: 2.73

CX LogP: 3.04

CX LogD: 3.02

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: -0.51

References

1. Suzuki F, Shimada J, Mizumoto H, Karasawa A, Kubo K, Nonaka H, Ishii A, Kawakita T..  (1992)  Adenosine A1 antagonists. 2. Structure-activity relationships on diuretic activities and protective effects against acute renal failure.,  35  (16): [PMID:1501234] [10.1021/jm00094a022]

2. Shimada J, Suzuki F, Nonaka H, Ishii A..  (1992)  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors.,  35  (5): [PMID:1548682] [10.1021/jm00083a018]

Source

Source(1):

• Scientific Literature