7-benzo[1,3]dioxol-5-ylmethyl-4,9-dimethyl-2-phenyl-7H-3,3a,5,7,8-pentaaza-cyclopenta[a]naphthalen-6-one

ID: ALA385683

PubChem CID: 11850147

Max Phase: Preclinical

Molecular Formula: C24H19N5O3

Molecular Weight: 425.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(Cc2ccc3c(c2)OCO3)c(=O)c2nc(C)n3nc(-c4ccccc4)cc3c12

Standard InChI:  InChI=1S/C24H19N5O3/c1-14-22-19-11-18(17-6-4-3-5-7-17)27-29(19)15(2)25-23(22)24(30)28(26-14)12-16-8-9-20-21(10-16)32-13-31-20/h3-11H,12-13H2,1-2H3

Standard InChI Key:  ZEAOAEIMQPOFMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.5061   -9.1948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148   -8.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884   -8.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5532   -7.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778   -7.7979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -9.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4498  -10.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5950   -6.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -5.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523   -4.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -4.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -4.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859   -4.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -3.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903   -3.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
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 19 20  2  0
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  8  9  2  0
  5 21  1  0
 10 11  1  0
  1 22  1  0
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  7 23  1  0
  1  2  2  0
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  3  2  1  0
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  3  4  2  0
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 12 13  2  0
 13 14  1  0
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  3  8  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA385683

   11-(1,3-Benzodioxol-5-ylmethyl)-7,13-dimethyl-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: 425.45

Molecular Weight (Monoisotopic): 425.1488

AlogP: 3.50

#Rotatable Bonds: 3

Polar Surface Area: 83.54

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.44

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