2-Methyl-6-(4-methylpiperazin-1-yl)-9-tetrahydropyran-4-yl-8-[2-(trifluoromethyl)phenyl]purine Hydrochloride

ID: ALA3092903

PubChem CID: 68603806

Max Phase: Preclinical

Molecular Formula: C23H28ClF3N6O

Molecular Weight: 460.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(N2CCN(C)CC2)c2nc(-c3ccccc3C(F)(F)F)n(C3CCOCC3)c2n1.Cl

Standard InChI:  InChI=1S/C23H27F3N6O.ClH/c1-15-27-21(31-11-9-30(2)10-12-31)19-22(28-15)32(16-7-13-33-14-8-16)20(29-19)17-5-3-4-6-18(17)23(24,25)26;/h3-6,16H,7-14H2,1-2H3;1H

Standard InChI Key:  RKBMMCQSHOXMNV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   34.8268  -31.0259    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.1159  -28.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1147  -29.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8296  -29.8576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8278  -28.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5432  -28.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5480  -29.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3355  -29.6909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8175  -29.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3277  -28.3537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8253  -27.3794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6424  -29.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5428  -26.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5423  -26.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8284  -25.7338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1133  -26.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1121  -26.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0571  -29.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8785  -29.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2907  -29.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8752  -28.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0475  -28.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3999  -29.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5947  -30.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0441  -31.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3006  -31.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1080  -32.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6586  -31.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4018  -30.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8290  -24.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6310  -27.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0393  -26.8676    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059  -27.5890    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.2132  -26.8673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  5 11  1  0
  9 12  1  0
 11 13  1  0
 11 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 12 22  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  3 23  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  8 24  1  0
 15 30  1  0
 22 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

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: 460.50

Molecular Weight (Monoisotopic): 460.2198

AlogP: 3.92

#Rotatable Bonds: 3

Polar Surface Area: 59.31

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.49

CX LogP: 3.97

CX LogD: 3.62

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: -1.28

References

1. Hollinshead SP, Tidwell MW, Palmer J, Guidetti R, Sanderson A, Johnson MP, Chambers MG, Oskins J, Stratford R, Astles PC..  (2013)  Selective cannabinoid receptor type 2 (CB2) agonists: optimization of a series of purines leading to the identification of a clinical candidate for the treatment of osteoarthritic pain.,  56  (14): [PMID:23795771] [10.1021/jm400305d]

Source

Source(1):

• Scientific Literature