3-(5-chloro-2,4-dimethoxy-phenyl)-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione

ID: ALA5219727

PubChem CID: 165416262

Max Phase: Preclinical

Molecular Formula: C13H10ClF3N2O4

Molecular Weight: 350.68

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(-n2c(=O)cc(C(F)(F)F)[nH]c2=O)cc1Cl

Standard InChI:  InChI=1S/C13H10ClF3N2O4/c1-22-8-4-9(23-2)7(3-6(8)14)19-11(20)5-10(13(15,16)17)18-12(19)21/h3-5H,1-2H3,(H,18,21)

Standard InChI Key:  GGXGVBQCYFQKID-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -1.4280   -0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.2051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -2.2672    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.0300    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.8548    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -1.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7153    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323   -0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323   -1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -1.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    1.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    2.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    2.2672    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    1.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  2  0
  6  5  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  4 11  2  0
  3 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  1  0
 14 22  1  0
  2 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5219727

   ---

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: 350.68

Molecular Weight (Monoisotopic): 350.0281

AlogP: 2.22

#Rotatable Bonds: 3

Polar Surface Area: 73.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.04

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -0.96

References

1. Günther J, Hillig RC, Zimmermann K, Kaulfuss S, Lemos C, Nguyen D, Rehwinkel H, Habgood M, Lechner C, Neuhaus R, Ganzer U, Drewes M, Chai J, Bouché L..  (2022)  BAY-069, a Novel (Trifluoromethyl)pyrimidinedione-Based BCAT1/2 Inhibitor and Chemical Probe.,  65  (21.0): [PMID:36261130] [10.1021/acs.jmedchem.2c00441]

2. Bertrand, Sophie M SM and 31 more authors.  2015-09-24  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits.  [PMID:26090771]

Source

Source(1):

• Scientific Literature