6-methoxy-3,8-dimethyl-N-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

ID: ALA1939804

PubChem CID: 46239228

Max Phase: Preclinical

Molecular Formula: C19H24N4O2

Molecular Weight: 340.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c2nc3[nH]nc(C)c3c(NCC3CCOCC3)c2c1

Standard InChI:  InChI=1S/C19H24N4O2/c1-11-8-14(24-3)9-15-17(11)21-19-16(12(2)22-23-19)18(15)20-10-13-4-6-25-7-5-13/h8-9,13H,4-7,10H2,1-3H3,(H2,20,21,22,23)

Standard InChI Key:  VFFZRVLFFCXMEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.8491    2.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503    1.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    2.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    2.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4220    1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071    1.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    2.6662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9973    2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    1.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968    1.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    1.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    2.5234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653    0.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1402    3.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    1.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2737    1.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068    0.1908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9926   -0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243   -2.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0140   -2.6985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955   -2.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2872   -1.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
  3  6  2  0
 11 14  1  0
  6  7  1  0
  4 15  1  0
  7 10  2  0
  2 16  1  0
  1  2  2  0
 16 17  1  0
  9  8  2  0
  7 18  1  0
  8  5  1  0
 18 19  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  5  4  2  0
  4  1  1  0
  2  3  1  0
  5  6  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1939804

   6-methoxy-3,8-dimethyl-N-(oxan-4-ylmethyl)-2H-pyrazolo[3,4-b]quinolin-4-amine

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: 340.43

Molecular Weight (Monoisotopic): 340.1899

AlogP: 3.58

#Rotatable Bonds: 4

Polar Surface Area: 72.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.46

CX Basic pKa: 4.52

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.94

References

1. Ho GD, Yang SW, Smotryski J, Bercovici A, Nechuta T, Smith EM, McElroy W, Tan Z, Tulshian D, McKittrick B, Greenlee WJ, Hruza A, Xiao L, Rindgen D, Mullins D, Guzzi M, Zhang X, Bleickardt C, Hodgson R..  (2012)  The discovery of potent, selective, and orally active pyrazoloquinolines as PDE10A inhibitors for the treatment of Schizophrenia.,  22  (2): [PMID:22222034] [10.1016/j.bmcl.2011.11.127]

Source

Source(1):

• Scientific Literature