8-methoxy-1-(4-methoxyphenyl)-3H-pyridazino[4,5-b]indol-4(5H)-one

ID: ALA3338886

PubChem CID: 136044190

Max Phase: Preclinical

Molecular Formula: C18H15N3O3

Molecular Weight: 321.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2n[nH]c(=O)c3[nH]c4ccc(OC)cc4c23)cc1

Standard InChI:  InChI=1S/C18H15N3O3/c1-23-11-5-3-10(4-6-11)16-15-13-9-12(24-2)7-8-14(13)19-17(15)18(22)21-20-16/h3-9,19H,1-2H3,(H,21,22)

Standard InChI Key:  IPDBYSDTJNQVBN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    9.3550   -4.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -5.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0619   -5.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0601   -3.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7687   -4.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690   -5.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5520   -5.4486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5516   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0357   -4.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8510   -4.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1885   -3.9471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7043   -3.2800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8827   -3.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6472   -3.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6470   -3.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3301   -5.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4017   -2.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7384   -1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2582   -1.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4447   -1.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1137   -2.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5959   -2.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9629   -0.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2936    0.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  1 14  1  0
 14 15  1  0
 10 16  2  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3338886

   ---

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: 321.34

Molecular Weight (Monoisotopic): 321.1113

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 80.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.27

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.46

References

1. Bruel A, Bénéteau R, Chabanne M, Lozach O, Le Guevel R, Ravache M, Bénédetti H, Meijer L, Logé C, Robert JM..  (2014)  Synthesis of new pyridazino[4,5-b]indol-4-ones and pyridazin-3(2H)-one analogs as DYRK1A inhibitors.,  24  (21): [PMID:25248682] [10.1016/j.bmcl.2014.09.017]

Source

Source(1):

• Scientific Literature