7-benzyl-4,9-dimethyl-2-pyridin-3-yl-7H-3,3a,5,7,8-pentaaza-cyclopenta[a]naphthalen-6-one

ID: ALA212397

PubChem CID: 11850012

Max Phase: Preclinical

Molecular Formula: C22H18N6O

Molecular Weight: 382.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(Cc2ccccc2)c(=O)c2nc(C)n3nc(-c4cccnc4)cc3c12

Standard InChI:  InChI=1S/C22H18N6O/c1-14-20-19-11-18(17-9-6-10-23-12-17)26-28(19)15(2)24-21(20)22(29)27(25-14)13-16-7-4-3-5-8-16/h3-12H,13H2,1-2H3

Standard InChI Key:  ANFPYGBSFPVDQM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   11.3339  -17.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1625  -17.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5767  -16.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1702  -15.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3377  -15.7824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9196  -16.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3301  -18.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9157  -17.9228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5729  -17.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1602  -18.6348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7099  -19.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4625  -18.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3777  -18.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9287  -15.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3456  -14.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1704  -14.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5872  -13.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1782  -12.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3481  -12.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9351  -13.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770  -19.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1708  -20.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8844  -20.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6012  -20.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5999  -19.3232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8857  -18.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9186  -19.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4026  -16.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0938  -16.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0
  5 14  1  0
 14 15  1  0
  1  2  2  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
  9  2  1  0
 17 18  2  0
  1  8  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
 20 15  1  0
  1  6  1  0
 12 21  1  0
  2  3  1  0
 21 22  2  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
 10 11  1  0
 25 26  2  0
 26 21  1  0
 11 12  2  0
  7 27  1  0
 12 13  1  0
  3 28  1  0
 13  9  2  0
  6 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA212397

   11-Benzyl-7,13-dimethyl-4-pyridin-3-yl-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: 382.43

Molecular Weight (Monoisotopic): 382.1542

AlogP: 3.17

#Rotatable Bonds: 3

Polar Surface Area: 77.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.18

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.77

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