4,9-dimethyl-2-phenyl-7-propyl-7H-3,3a,5,7,8-pentaaza-cyclopenta[a]naphthalen-6-one

ID: ALA212085

PubChem CID: 11850775

Max Phase: Preclinical

Molecular Formula: C19H19N5O

Molecular Weight: 333.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1nc(C)c2c(nc(C)n3nc(-c4ccccc4)cc23)c1=O

Standard InChI:  InChI=1S/C19H19N5O/c1-4-10-23-19(25)18-17(12(2)21-23)16-11-15(14-8-6-5-7-9-14)22-24(16)13(3)20-18/h5-9,11H,4,10H2,1-3H3

Standard InChI Key:  NRCYHHOMJQHXHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.1481   -2.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5894   -1.4894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979   -0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3711   -0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9827   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168    0.6921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2436    0.6656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364   -0.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4614   -0.0920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395   -1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219   -2.1565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -2.7442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152   -2.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1320   -1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -2.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555   -3.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -3.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1733   -3.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389   -2.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093   -2.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577    0.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6783    1.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    2.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226    2.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  3  4  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  3  8  1  0
 13 15  1  0
  4  5  1  0
 15 16  2  0
  5  6  2  0
 16 17  1  0
  6  7  1  0
 17 18  2  0
  7  8  1  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  8  9  2  0
  5 21  1  0
 10 11  1  0
  1 22  1  0
  1 11  1  0
  7 23  1  0
  1  2  2  0
 23 24  1  0
 10  4  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA212085

   7,13-Dimethyl-4-phenyl-11-propyl-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: 333.40

Molecular Weight (Monoisotopic): 333.1590

AlogP: 3.13

#Rotatable Bonds: 3

Polar Surface Area: 65.08

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -1.75

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