US9180122, 33

ID: ALA3972972

PubChem CID: 71187214

Max Phase: Preclinical

Molecular Formula: C12H11NO4S

Molecular Weight: 265.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]cc(S(=O)(=O)Cc2ccccc2)cc1O

Standard InChI:  InChI=1S/C12H11NO4S/c14-11-6-10(7-13-12(11)15)18(16,17)8-9-4-2-1-3-5-9/h1-7,14H,8H2,(H,13,15)

Standard InChI Key:  NBOYOQSSTOIRMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  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 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
    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
    0.0000    3.0008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394    3.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006    4.2008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993    3.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5967    6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937    7.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2931    8.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    6.0003    0.0000 C   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  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3972972

   5-(benzylsulfonyl)-3-hydroxypyridin-2(1H)-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: 265.29

Molecular Weight (Monoisotopic): 265.0409

AlogP: 1.05

#Rotatable Bonds: 3

Polar Surface Area: 87.23

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: ┄

CX LogP: 0.39

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.87

Np Likeness Score: -0.86

References

1.  (2015)  5- or 6-substituted 3-hydroxy-2 (1 H)-pyridinones as D-amino acid oxidase (DAAO) inhibitors in therapy of diseases such as schizophrenia, cognitive disorder and pain, 

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