US9290456, 65

ID: ALA3986233

PubChem CID: 71273870

Max Phase: Preclinical

Molecular Formula: C13H10ClF3N2O2

Molecular Weight: 318.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]nc(CCc2ccc(C(F)(F)F)c(Cl)c2)cc1O

Standard InChI:  InChI=1S/C13H10ClF3N2O2/c14-10-5-7(2-4-9(10)13(15,16)17)1-3-8-6-11(20)12(21)19-18-8/h2,4-6H,1,3H2,(H,18,20)(H,19,21)

Standard InChI Key:  UVPPWVJMJLWMDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  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
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    8.1004    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    9.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460   10.3518    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2677   10.3508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066   10.9511    0.0000 F   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  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 11  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986233

   6-[2-[3-Chloro-4-(trifluoromethyl)phenyl]ethyl]-1,2-dihydropyridazine-3,4-dione

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: 318.68

Molecular Weight (Monoisotopic): 318.0383

AlogP: 2.93

#Rotatable Bonds: 3

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: 7.34

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: -0.86

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