4-(2,4-dichlorobenzyloxy)-3-methyl-1-(7H-purin-6-yl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

ID: ALA4091396

PubChem CID: 137654391

Max Phase: Preclinical

Molecular Formula: C19H15Cl2N7O2

Molecular Weight: 444.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2ncnc3nc[nH]c23)c2c1C(OCc1ccc(Cl)cc1Cl)CC(=O)N2

Standard InChI:  InChI=1S/C19H15Cl2N7O2/c1-9-15-13(30-6-10-2-3-11(20)4-12(10)21)5-14(29)26-18(15)28(27-9)19-16-17(23-7-22-16)24-8-25-19/h2-4,7-8,13H,5-6H2,1H3,(H,26,29)(H,22,23,24,25)

Standard InChI Key:  GTFVCAGVTWPZTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    0.0045   -8.8755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -8.2253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -8.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3190   -9.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6022   -9.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919  -10.2480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966  -10.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135  -10.2676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0255   -9.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -9.0436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -8.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8335   -8.2365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0353   -8.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -9.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194  -10.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158  -10.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0717   -9.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314   -8.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -7.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559  -11.1294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3861   -8.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1831   -8.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7378   -7.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5346   -8.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0890   -7.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8468   -6.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0451   -6.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941   -7.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7744   -8.9117    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4007   -6.1489    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
  2  3  1  0
  3  1  2  0
  4  5  2  0
  4  9  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12 10  1  0
 13 14  2  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 16 20  2  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 24 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091396

   ---

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: 444.28

Molecular Weight (Monoisotopic): 443.0664

AlogP: 3.75

#Rotatable Bonds: 4

Polar Surface Area: 110.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.17

CX Basic pKa: 2.09

CX LogP: 2.61

CX LogD: 2.60

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.17

References

1. Frimurer TM, Mende F, Graae AS, Engelstoft MS, Egerod KL, Nygaard R, Gerlach LO, Hansen JB, Schwartz TW, Holst B..  (2017)  Model-Based Discovery of Synthetic Agonists for the Zn2+-Sensing G-Protein-Coupled Receptor 39 (GPR39) Reveals Novel Biological Functions.,  60  (3): [PMID:28045522] [10.1021/acs.jmedchem.6b00648]

Source

Source(1):

• Scientific Literature