3-benzyl-1-[(dimethylamino)methyl]-6-methyl-9-phenylpyrazolo[1',5':1,6]pyrimido[4,5-d]pyridazin-4(3H)-one

ID: ALA377144

PubChem CID: 11850439

Max Phase: Preclinical

Molecular Formula: C25H24N6O

Molecular Weight: 424.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2c(=O)n(Cc3ccccc3)nc(CN(C)C)c2c2cc(-c3ccccc3)nn12

Standard InChI:  InChI=1S/C25H24N6O/c1-17-26-24-23(22-14-20(28-31(17)22)19-12-8-5-9-13-19)21(16-29(2)3)27-30(25(24)32)15-18-10-6-4-7-11-18/h4-14H,15-16H2,1-3H3

Standard InChI Key:  NWOYPSQSXFBTCX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   10.8582  -16.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6865  -16.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1006  -15.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6927  -14.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8629  -14.9169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4441  -15.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8558  -17.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4371  -17.0593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0975  -17.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6847  -17.7707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2348  -18.3829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9862  -18.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9029  -17.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6995  -18.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6938  -19.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4070  -19.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4079  -18.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4431  -18.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1250  -18.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1282  -19.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6187  -15.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4545  -14.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8714  -13.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6963  -13.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -12.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7046  -12.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8750  -12.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4619  -12.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9259  -15.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3416  -14.9256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1669  -14.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9319  -14.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13  9  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 20  2  0
 19 17  2  0
 17 14  1  0
  7 18  1  0
 19 20  1  0
  1  2  2  0
  1  6  1  0
  6 21  2  0
  2  3  1  0
  5 22  1  0
  3  4  2  0
 22 23  1  0
  4  5  1  0
 23 24  2  0
  5  6  1  0
 24 25  1  0
  7 10  1  0
 25 26  2  0
  7  8  2  0
 26 27  1  0
  9  2  1  0
 27 28  2  0
 28 23  1  0
  1  8  1  0
  3 29  1  0
  9 10  1  0
 29 30  1  0
 10 11  1  0
 30 31  1  0
 11 12  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA377144

   11-Benzyl-13-[(dimethylamino)methyl]-7-methyl-4-phenyl-5,6,8,11,12-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,12-pentaen-10-one

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: 424.51

Molecular Weight (Monoisotopic): 424.2012

AlogP: 3.52

#Rotatable Bonds: 5

Polar Surface Area: 68.32

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.24

CX LogP: 3.55

CX LogD: 3.32

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -1.41

References

1. Giovannoni MP, Vergelli C, Biancalani C, Cesari N, Graziano A, Biagini P, Gracia J, Gavaldà A, Dal Piaz V..  (2006)  Novel pyrazolopyrimidopyridazinones with potent and selective phosphodiesterase 5 (PDE5) inhibitory activity as potential agents for treatment of erectile dysfunction.,  49  (17): [PMID:16913726] [10.1021/jm060265+]

Source

Source(1):

• Scientific Literature