2-Chloro-9-((6-(tetrahydro-2H-pyran-4-yl)pyridin-2-yl)methyl)-9H-purin-6-amine

ID: ALA4789101

PubChem CID: 162668882

Max Phase: Preclinical

Molecular Formula: C16H17ClN6O

Molecular Weight: 344.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2Cc1cccc(C2CCOCC2)n1

Standard InChI:  InChI=1S/C16H17ClN6O/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/h1-3,9-10H,4-8H2,(H2,18,21,22)

Standard InChI Key:  RSXROEYEGKRILN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   12.0220   -6.0969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4934   -6.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0046   -7.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2324   -7.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5195   -7.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8185   -7.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8261   -6.3213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5390   -5.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2441   -6.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5507   -5.1053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2482   -8.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0474   -8.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6028   -7.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3978   -7.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6414   -8.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0860   -9.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2869   -9.1613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0178  -11.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7742  -10.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3296  -10.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1246  -10.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3683  -11.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8128  -11.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1057   -7.5373    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
 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:

   

   ALA4789101

   ---

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: 344.81

Molecular Weight (Monoisotopic): 344.1152

AlogP: 2.40

#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: 5.07

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -1.08

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