1-(4,4'-bipyridin-2-yl)-3-hydroxypyridin-4(1H)-one

ID: ALA3797584

PubChem CID: 127048056

Max Phase: Preclinical

Molecular Formula: C15H11N3O2

Molecular Weight: 265.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn(-c2cc(-c3ccncc3)ccn2)cc1O

Standard InChI:  InChI=1S/C15H11N3O2/c19-13-4-8-18(10-14(13)20)15-9-12(3-7-17-15)11-1-5-16-6-2-11/h1-10,20H

Standard InChI Key:  WVRJMFXIQHKRMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.5987   -1.5004    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 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 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
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8919   -5.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886   -6.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824   -8.2533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858   -7.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -5.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  1  2  1  0
  5  8  2  0
  6  9  1  0
  1 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  1  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797584

   ---

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: 265.27

Molecular Weight (Monoisotopic): 265.0851

AlogP: 2.00

#Rotatable Bonds: 2

Polar Surface Area: 68.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.66

CX Basic pKa: 5.09

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.77

Np Likeness Score: -0.70

References

1. Zhao Z, Harrison ST, Schubert JW, Sanders JM, Polsky-Fisher S, Zhang NR, McLoughlin D, Gibson CR, Robinson RG, Sachs NA, Kandebo M, Yao L, Smith SM, Hutson PH, Wolkenberg SE, Barrow JC..  (2016)  Synthesis and optimization of N-heterocyclic pyridinones as catechol-O-methyltransferase (COMT) inhibitors.,  26  (12): [PMID:27133481] [10.1016/j.bmcl.2016.03.095]

Source

Source(1):

• Scientific Literature