US9290456, 55

ID: ALA3986099

PubChem CID: 71505690

Max Phase: Preclinical

Molecular Formula: C13H8F6N2O2

Molecular Weight: 338.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]nc(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc1O

Standard InChI:  InChI=1S/C13H8F6N2O2/c14-12(15,16)7-1-6(2-8(4-7)13(17,18)19)3-9-5-10(22)11(23)21-20-9/h1-2,4-5H,3H2,(H,20,22)(H,21,23)

Standard InChI Key:  YMEUAOOCXBLSPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  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
   -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
   -5.1992    2.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2409    3.5812    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947    1.7855    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2361    2.3814    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160    7.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    8.1000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    8.0918    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    8.6957    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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 12 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986099

   6-{[3,5-bis(Trifluoromethyl)phenyl]methyl}-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: 338.21

Molecular Weight (Monoisotopic): 338.0490

AlogP: 3.10

#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: 6.54

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: -0.70

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