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

ID: ALA1078922

PubChem CID: 45102742

Max Phase: Preclinical

Molecular Formula: C22H26N6O

Molecular Weight: 390.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(C2=NOC(Cn3cnc4c(N5CCCC5)ncnc43)C2)c(C)c1

Standard InChI:  InChI=1S/C22H26N6O/c1-14-8-15(2)19(16(3)9-14)18-10-17(29-26-18)11-28-13-25-20-21(23-12-24-22(20)28)27-6-4-5-7-27/h8-9,12-13,17H,4-7,10-11H2,1-3H3

Standard InChI Key:  QGIJYIKCDJDZLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.6141   -0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3289   -1.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3271    0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0425    0.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0427   -0.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8332   -0.8965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3215   -0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8328    0.4482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0883   -1.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4021   -2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1854   -2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1835   -1.2614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3991   -1.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8530   -2.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8489   -3.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5610   -3.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2780   -3.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2785   -2.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5658   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5666   -1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9915   -3.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1326   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3246    1.4253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9874    1.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7301    2.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9051    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6526    1.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  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
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078922

   5-[(6-Pyrrolidin-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: 390.49

Molecular Weight (Monoisotopic): 390.2168

AlogP: 3.54

#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: 4.32

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -1.00

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