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

ID: ALA3338885

PubChem CID: 136044191

Max Phase: Preclinical

Molecular Formula: C17H13N3O2

Molecular Weight: 291.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]c3c(=O)[nH]nc(-c4ccccc4)c3c2c1

Standard InChI:  InChI=1S/C17H13N3O2/c1-22-11-7-8-13-12(9-11)14-15(10-5-3-2-4-6-10)19-20-17(21)16(14)18-13/h2-9,18H,1H3,(H,20,21)

Standard InChI Key:  DLZOJLRQZZCTRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.6318   -5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6306   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3387   -6.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3369   -4.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0455   -5.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -6.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8283   -4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -5.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1278   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4653   -4.7726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811   -4.1055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594   -4.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -4.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -3.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6069   -6.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785   -3.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -2.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -2.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7214   -2.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904   -2.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726   -3.6180    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
M  END

Alternative Forms

1. Parent:

   

   ALA3338885

   ---

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: 291.31

Molecular Weight (Monoisotopic): 291.1008

AlogP: 3.08

#Rotatable Bonds: 2

Polar Surface Area: 70.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.27

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: -0.56

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