6-(3,4-Dichlorophenyl)pyrimidine-4-carboxylic Acid

ID: ALA3407866

Cas Number: 1207723-55-4

PubChem CID: 44633034

Max Phase: Preclinical

Molecular Formula: C11H6Cl2N2O2

Molecular Weight: 269.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(Cl)c(Cl)c2)ncn1

Standard InChI:  InChI=1S/C11H6Cl2N2O2/c12-7-2-1-6(3-8(7)13)9-4-10(11(16)17)15-5-14-9/h1-5H,(H,16,17)

Standard InChI Key:  FPVPSYCVUOIXCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    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 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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 O   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
    2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945    3.0046    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
    2.5964    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    4.9525    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2328    3.6062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 10  1  0
 14 16  1  0
 13 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3407866

   6-(3,4-Dichlorophenyl)pyrimidine-4-carboxylic acid

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: 269.09

Molecular Weight (Monoisotopic): 267.9806

AlogP: 3.15

#Rotatable Bonds: 2

Polar Surface Area: 63.08

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.76

CX Basic pKa: 5.25

CX LogP: 1.70

CX LogD: 0.00

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.91

Np Likeness Score: -1.20

References

1. Toledo-Sherman LM, Prime ME, Mrzljak L, Beconi MG, Beresford A, Brookfield FA, Brown CJ, Cardaun I, Courtney SM, Dijkman U, Hamelin-Flegg E, Johnson PD, Kempf V, Lyons K, Matthews K, Mitchell WL, O'Connell C, Pena P, Powell K, Rassoulpour A, Reed L, Reindl W, Selvaratnam S, Friley WW, Weddell DA, Went NE, Wheelan P, Winkler C, Winkler D, Wityak J, Yarnold CJ, Yates D, Munoz-Sanjuan I, Dominguez C..  (2015)  Development of a series of aryl pyrimidine kynurenine monooxygenase inhibitors as potential therapeutic agents for the treatment of Huntington's disease.,  58  (3): [PMID:25590515] [10.1021/jm501350y]

2. Amin SA, Adhikari N, Jha T, Gayen S..  (2016)  First molecular modeling report on novel arylpyrimidine kynurenine monooxygenase inhibitors through multi-QSAR analysis against Huntington's disease: A proposal to chemists!,  26  (23): [PMID:27838184] [10.1016/j.bmcl.2016.10.058]

3. Ahamad S, Bhat SA..  (2022)  The Emerging Landscape of Small-Molecule Therapeutics for the Treatment of Huntington's Disease.,  65  (24.0): [PMID:36490325] [10.1021/acs.jmedchem.2c00799]

Source

Source(1):

• Scientific Literature