2-Chloro-9-((6-cyclopentylpyridin-2-yl)methyl)-9H-purin-6-amine

ID: ALA4790482

PubChem CID: 162668470

Max Phase: Preclinical

Molecular Formula: C16H17ClN6

Molecular Weight: 328.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2Cc1cccc(C2CCCC2)n1

Standard InChI:  InChI=1S/C16H17ClN6/c17-16-21-14(18)13-15(22-16)23(9-19-13)8-11-6-3-7-12(20-11)10-4-1-2-5-10/h3,6-7,9-10H,1-2,4-5,8H2,(H2,18,21,22)

Standard InChI Key:  OJCLSOHWOVKXMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   12.4728   -6.1581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9501   -6.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4631   -7.4804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6886   -7.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9753   -7.6272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2704   -7.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2789   -6.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9881   -5.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6929   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9925   -5.1757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7097   -8.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5104   -8.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -7.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8570   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1036   -8.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5536   -9.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7570   -9.2150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8002  -10.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5789  -10.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5704  -11.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7906  -11.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3173  -10.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5612   -7.6166    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
  8 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 16 18  1  0
 11 12  1  0
  3 11  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790482

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.81

Molecular Weight (Monoisotopic): 328.1203

AlogP: 3.16

#Rotatable Bonds: 3

Polar Surface Area: 82.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.13

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -1.05

References

1. Huang Y,Wu XN,Zhou Q,Wu Y,Zheng D,Li Z,Guo L,Luo HB.  (2020)  Rational Design of 2-Chloroadenine Derivatives as Highly Selective Phosphodiesterase 8A Inhibitors.,  63  (24): [PMID:33291877] [10.1021/acs.jmedchem.0c01573]

Source

Source(1):

• Scientific Literature