US9290456, 43

ID: ALA3975855

PubChem CID: 71270492

Max Phase: Preclinical

Molecular Formula: C11H8ClFN2O2

Molecular Weight: 254.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]nc(Cc2c(F)cccc2Cl)cc1O

Standard InChI:  InChI=1S/C11H8ClFN2O2/c12-8-2-1-3-9(13)7(8)4-6-5-10(16)11(17)15-14-6/h1-3,5H,4H2,(H,14,16)(H,15,17)

Standard InChI Key:  DVQGQOMJOMJZDZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    5.8530    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963    1.7949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  7  8  2  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 10  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3975855

   6-(2-Chloro-6-fluorobenzyl)-4-hydroxypyridazin-3(2H)-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: 254.65

Molecular Weight (Monoisotopic): 254.0258

AlogP: 1.86

#Rotatable Bonds: 2

Polar Surface Area: 65.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.91

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.86

Np Likeness Score: -1.47

References

1.  (2016)  Pyridazinone compounds and their use as DAAO inhibitors, 

2. Raje, Mithun and 9 more authors.  2013-07-01  Synthesis of kojic acid derivatives as secondary binding site probes of D-amino acid oxidase.  [PMID:23683589]

3. Hin, Niyada and 10 more authors.  2015-09-24  6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel D-Amino Acid Oxidase Inhibitors.  [PMID:26309148]

4. Hin, Niyada and 8 more authors.  2016-04-15  D-Amino acid oxidase inhibitors based on the 5-hydroxy-1,2,4-triazin-6(1H)-one scaffold.  [PMID:26965861]

5. Kato, Yusuke and 9 more authors.  2018-11-05  Structural basis for potent inhibition of d-amino acid oxidase by thiophene carboxylic acids.  [PMID:30265959]

Source

Source(1):

• BindingDB Database