3-mesityl-5-((6-(piperidin-1-yl)-9H-purin-9-yl)methyl)-4,5-dihydroisoxazole

ID: ALA1079199

PubChem CID: 45102740

Max Phase: Preclinical

Molecular Formula: C23H28N6O

Molecular Weight: 404.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(C2=NOC(Cn3cnc4c(N5CCCCC5)ncnc43)C2)c(C)c1

Standard InChI:  InChI=1S/C23H28N6O/c1-15-9-16(2)20(17(3)10-15)19-11-18(30-27-19)12-29-14-26-21-22(24-13-25-23(21)29)28-7-5-4-6-8-28/h9-10,13-14,18H,4-8,11-12H2,1-3H3

Standard InChI Key:  FFBNKDKGKJHHMM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   -5.2348   -0.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2359   -1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5211   -1.5277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229    0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8075   -0.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073   -1.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0168   -1.3715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285   -0.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172   -0.0268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4479   -2.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -2.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665   -1.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509   -1.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011   -3.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110   -4.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -3.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -3.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -2.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7166   -1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -4.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7174   -4.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254    0.9503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8102    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5246    2.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2397    2.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2408    1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  5  4  2  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
  7 10  1  0
 21 22  1  0
  5  6  1  0
 19 23  1  0
 10 11  1  0
 17 24  1  0
 11 12  1  0
  4 25  1  0
 25 26  1  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
 12 13  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079199

   5-[(6-Piperidin-1-ylpurin-9-yl)methyl]-3-(2,4,6-trimethylphenyl)-4,5-dihydro-1,2-oxazole

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: 404.52

Molecular Weight (Monoisotopic): 404.2325

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 68.43

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.59

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -0.98

References

1. Thalassitis A, Hadjipavlou-Litina DJ, Litinas KE, Miltiadou P..  (2009)  Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition.,  19  (22): [PMID:19811914] [10.1016/j.bmcl.2009.09.040]

Source

Source(1):

• Scientific Literature