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

ID: ALA1078923

PubChem CID: 45102743

Max Phase: Preclinical

Molecular Formula: C18H18ClN5O

Molecular Weight: 355.83

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18ClN5O/c1-10-4-11(2)15(12(3)5-10)14-6-13(25-23-14)7-24-9-22-16-17(19)20-8-21-18(16)24/h4-5,8-9,13H,6-7H2,1-3H3

Standard InChI Key:  SEQZTAPOGKQIKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -5.9394   -7.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9406   -8.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258   -9.1577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2276   -7.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121   -7.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118   -8.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213   -9.0014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329   -8.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217   -7.6567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4661   -9.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6419   -9.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523  -10.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3689  -10.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -9.3665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553   -9.1136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013  -10.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053  -11.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069  -11.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240  -11.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244  -10.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0116  -10.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -9.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374  -11.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217  -11.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2300   -6.6795    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  1  2  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA1078923

   5-[(6-Chloropurin-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: 355.83

Molecular Weight (Monoisotopic): 355.1200

AlogP: 3.60

#Rotatable Bonds: 3

Polar Surface Area: 65.19

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.78

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -0.85

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