2-Chloro-9-((6-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yl)methyl)-9H-purin-6-amine

ID: ALA4745958

PubChem CID: 162647729

Max Phase: Preclinical

Molecular Formula: C16H15ClN6O

Molecular Weight: 342.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2Cc1cccc(C2=CCOCC2)n1

Standard InChI:  InChI=1S/C16H15ClN6O/c17-16-21-14(18)13-15(22-16)23(9-19-13)8-11-2-1-3-12(20-11)10-4-6-24-7-5-10/h1-4,9H,5-8H2,(H2,18,21,22)

Standard InChI Key:  MFFVTRPKTJJSSG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   11.1044   -6.0775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5865   -6.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1083   -7.3999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3303   -7.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6224   -7.5582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9163   -7.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9139   -6.3345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6176   -5.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3279   -6.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6193   -5.1066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3611   -8.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1600   -8.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7060   -7.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5049   -7.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7619   -8.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2158   -9.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4169   -9.1213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1754  -11.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9226  -10.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4686  -10.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2675  -10.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5203  -11.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9784  -11.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2084   -7.5623    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  2  0
 21 22  1  0
 22 23  1  0
 18 23  1  0
 16 20  1  0
 11 12  1  0
  3 11  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745958

   ---

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: 342.79

Molecular Weight (Monoisotopic): 342.0996

AlogP: 2.31

#Rotatable Bonds: 3

Polar Surface Area: 91.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.22

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -0.61

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