4,9-dimethyl-2-phenyl-7-(2-piperidin-4-yl-ethyl)-7H-3,3a,5,7,8-pentaaza-cyclopenta[a]naphthalen-6-one

ID: ALA386514

PubChem CID: 11849944

Max Phase: Preclinical

Molecular Formula: C23H26N6O

Molecular Weight: 402.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(CCC2CCNCC2)c(=O)c2nc(C)n3nc(-c4ccccc4)cc3c12

Standard InChI:  InChI=1S/C23H26N6O/c1-15-21-20-14-19(18-6-4-3-5-7-18)27-29(20)16(2)25-22(21)23(30)28(26-15)13-10-17-8-11-24-12-9-17/h3-7,14,17,24H,8-13H2,1-2H3

Standard InChI Key:  JWELNRYLAYAYQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    4.2925  -18.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513  -17.9126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2427  -17.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695  -17.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579  -16.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0238  -15.7311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1970  -15.7575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042  -16.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792  -16.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5012  -17.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1188  -18.5797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899  -19.1674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4254  -18.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086  -17.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1555  -19.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1852  -20.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9144  -20.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6139  -19.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5796  -19.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8499  -18.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2829  -16.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076  -19.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7623  -15.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527  -14.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180  -13.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1126  -12.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814  -12.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559  -12.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633  -12.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963  -13.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 25 26  1  0
  3  2  1  0
  3  4  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA386514

   7,13-Dimethyl-4-phenyl-11-(2-piperidin-4-ylethyl)-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: 402.50

Molecular Weight (Monoisotopic): 402.2168

AlogP: 3.11

#Rotatable Bonds: 4

Polar Surface Area: 77.11

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.36

CX LogP: 2.40

CX LogD: -0.37

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.28

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