2-[4-(4-chlorobenzyloxy)-3-cyano]phenylpyrimidine-5-carboxylic acid

ID: ALA5207426

PubChem CID: 168295718

Max Phase: Preclinical

Molecular Formula: C19H12ClN3O3

Molecular Weight: 365.78

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ncc(C(=O)O)cn2)ccc1OCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H12ClN3O3/c20-16-4-1-12(2-5-16)11-26-17-6-3-13(7-14(17)8-21)18-22-9-15(10-23-18)19(24)25/h1-7,9-10H,11H2,(H,24,25)

Standard InChI Key:  ZFDLCRWMTXDSMU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.0013    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -0.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281    1.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    2.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    1.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    1.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -2.2665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    2.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    3.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    1.8566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -0.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -1.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427   -2.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704   -2.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720   -1.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -3.0942    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
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  7  3  1  0
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  5 13  1  0
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 10 15  1  0
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  6 18  1  0
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 21 20  2  0
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 24 23  1  0
 25 24  2  0
 20 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207426

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.78

Molecular Weight (Monoisotopic): 365.0567

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 96.10

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.84

CX Basic pKa: 1.02

CX LogP: 3.92

CX LogD: 0.64

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.29

References

1. Zhao J, Mao Q, Lin F, Zhang B, Sun M, Zhang T, Wang S..  (2022)  Intramolecular hydrogen bond interruption and scaffold hopping of TMC-5 led to 2-(4-alkoxy-3-cyanophenyl)pyrimidine-4/5-carboxylic acids and 6-(4-alkoxy-3-cyanophenyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-ones as potent pyrimidine-based xanthine oxidase inhibitors.,  229  [PMID:34992040] [10.1016/j.ejmech.2021.114086]

Source

Source(1):

• Scientific Literature