US9180122, 18

ID: ALA3982073

PubChem CID: 71187297

Max Phase: Preclinical

Molecular Formula: C11H10N2O2S

Molecular Weight: 234.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]cc(SCc2ccncc2)cc1O

Standard InChI:  InChI=1S/C11H10N2O2S/c14-10-5-9(6-13-11(10)15)16-7-8-1-3-12-4-2-8/h1-6,14H,7H2,(H,13,15)

Standard InChI Key:  BYFSNTWEWSYYLX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  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
   -0.0031    3.0008    0.0000 S   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 N   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
   -0.0080    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  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982073

   3-Hydroxy-5-[(pyridin-4-ylmethyl)sulfanyl]pyridin-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: 234.28

Molecular Weight (Monoisotopic): 234.0463

AlogP: 1.77

#Rotatable Bonds: 3

Polar Surface Area: 65.98

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.61

CX Basic pKa: 5.03

CX LogP: 0.67

CX LogD: 0.65

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.79

Np Likeness Score: -0.82

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