8-(4-Methoxy-2-methyl-phenyl)-2-methyl-6-(4-methylpiperazin-1-yl)-9-tetrahydropyran-4-yl-purine Hydrochloride

ID: ALA3092890

PubChem CID: 71762083

Max Phase: Preclinical

Molecular Formula: C24H33ClN6O2

Molecular Weight: 436.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc3c(N4CCN(C)CC4)nc(C)nc3n2C2CCOCC2)c(C)c1.Cl

Standard InChI:  InChI=1S/C24H32N6O2.ClH/c1-16-15-19(31-4)5-6-20(16)22-27-21-23(29-11-9-28(3)10-12-29)25-17(2)26-24(21)30(22)18-7-13-32-14-8-18;/h5-6,15,18H,7-14H2,1-4H3;1H

Standard InChI Key:  LYQAMNVBFGVZHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    9.1045  -23.8071    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8070  -21.1634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8059  -21.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207  -22.4036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188  -20.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343  -21.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2392  -21.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267  -22.2370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087  -21.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188  -20.8997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164  -19.9255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336  -21.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338  -19.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334  -18.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195  -18.2798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045  -18.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032  -19.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7483  -22.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5697  -22.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9819  -21.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5664  -20.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7387  -20.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911  -22.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858  -23.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353  -23.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917  -24.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7992  -24.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499  -23.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0930  -23.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5202  -17.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3222  -20.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8069  -21.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2209  -22.2670    0.0000 C   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
 20 32  1  0
 32 33  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: 436.56

Molecular Weight (Monoisotopic): 436.2587

AlogP: 3.22

#Rotatable Bonds: 4

Polar Surface Area: 68.54

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.49

CX LogP: 3.40

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -1.14

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