1-(biphenyl-3-yl)-5-hydroxy-2-(hydroxy(phenyl)methyl)pyridin-4(1H)-one

ID: ALA3425739

PubChem CID: 118736607

Max Phase: Preclinical

Molecular Formula: C24H19NO3

Molecular Weight: 369.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(C(O)c2ccccc2)n(-c2cccc(-c3ccccc3)c2)cc1O

Standard InChI:  InChI=1S/C24H19NO3/c26-22-15-21(24(28)18-10-5-2-6-11-18)25(16-23(22)27)20-13-7-12-19(14-20)17-8-3-1-4-9-17/h1-16,24,27-28H

Standard InChI Key:  WPLQBESTXAGXJC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    0.0000    1.5000    0.0000 N   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
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    6.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5939    6.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955    5.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 21  1  0
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 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3425739

   ---

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: 369.42

Molecular Weight (Monoisotopic): 369.1365

AlogP: 4.29

#Rotatable Bonds: 4

Polar Surface Area: 62.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.16

CX Basic pKa: 2.09

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.22

References

1. Harrison ST, Poslusney MS, Mulhearn JJ, Zhao Z, Kett NR, Schubert JW, Melamed JY, Allison TJ, Patel SB, Sanders JM, Sharma S, Smith RF, Hall DL, Robinson RG, Sachs NA, Hutson PH, Wolkenberg SE, Barrow JC..  (2015)  Synthesis and Evaluation of Heterocyclic Catechol Mimics as Inhibitors of Catechol-O-methyltransferase (COMT).,  6  (3): [PMID:25815153] [10.1021/ml500502d]

Source

Source(1):

• Scientific Literature