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

ID: ALA213265

PubChem CID: 11850145

Max Phase: Preclinical

Molecular Formula: C17H15N5O

Molecular Weight: 305.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(C)c(=O)c2nc(C)n3nc(-c4ccccc4)cc3c12

Standard InChI:  InChI=1S/C17H15N5O/c1-10-15-14-9-13(12-7-5-4-6-8-12)20-22(14)11(2)18-16(15)17(23)21(3)19-10/h4-9H,1-3H3

Standard InChI Key:  OGJPWJTVAFMNRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -3.0976   -0.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389   -0.2123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3206    0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    1.9693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932    1.9428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5860    1.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110    1.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890   -0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714   -0.8795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -1.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -0.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345   -1.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -2.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -2.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896   -1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071    1.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4825   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279    2.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 10  4  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA213265

   7,11,13-Trimethyl-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: 305.34

Molecular Weight (Monoisotopic): 305.1277

AlogP: 2.26

#Rotatable Bonds: 1

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: 1.93

CX LogD: 1.93

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -1.63

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