1-[4-[8-(2-Chlorophenyl)-9-(2-methoxyethyl)-2-methylpurin-6-yl]piperazin-1-yl]ethanone Hydrochloride

ID: ALA3092892

PubChem CID: 67434539

Max Phase: Preclinical

Molecular Formula: C21H26Cl2N6O2

Molecular Weight: 428.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCn1c(-c2ccccc2Cl)nc2c(N3CCN(C(C)=O)CC3)nc(C)nc21.Cl

Standard InChI:  InChI=1S/C21H25ClN6O2.ClH/c1-14-23-20(27-10-8-26(9-11-27)15(2)29)18-21(24-14)28(12-13-30-3)19(25-18)16-6-4-5-7-17(16)22;/h4-7H,8-13H2,1-3H3;1H

Standard InChI Key:  FZXBQRPZKNXVPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    7.4250  -14.1134    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4068  -11.7327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056  -12.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204  -12.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1186  -11.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340  -11.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387  -12.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263  -12.8063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081  -12.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184  -11.4692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161  -10.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9331  -12.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335  -10.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331   -9.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -8.8495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4041   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030  -10.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3478  -12.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1691  -12.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812  -12.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1658  -11.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3382  -11.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9217  -10.6999    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8857  -13.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372  -14.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968  -14.9887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0483  -15.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199   -8.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -7.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057   -7.6115    0.0000 O   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
 22 24  1  0
  8 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 15 29  1  0
 29 30  1  0
 29 31  2  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: 428.92

Molecular Weight (Monoisotopic): 428.1728

AlogP: 2.77

#Rotatable Bonds: 5

Polar Surface Area: 76.38

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.18

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -1.78

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