4-(4-Bromo-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-5-methoxy-2-(2-methylphenoxy)benzonitrile

ID: ALA5220805

PubChem CID: 156716021

Max Phase: Preclinical

Molecular Formula: C19H14BrN3O4

Molecular Weight: 428.24

Names and Identifiers

Canonical SMILES:  COc1cc(C#N)c(Oc2ccccc2C)cc1-n1c(=O)cc(Br)[nH]c1=O

Standard InChI:  InChI=1S/C19H14BrN3O4/c1-11-5-3-4-6-14(11)27-15-8-13(16(26-2)7-12(15)10-21)23-18(24)9-17(20)22-19(23)25/h3-9H,1-2H3,(H,22,25)

Standard InChI Key:  ANGPOJJDTUIZLT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.1425   -1.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -1.4415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -2.6791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296   -1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567    0.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    1.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    2.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    2.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551    2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180   -2.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323   -2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -2.6790    0.0000 Br  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
  4  7  2  0
  3  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
 11 14  1  0
 14 15  3  0
 10 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
  2 23  2  0
 18 24  1  0
 13 25  1  0
 25 26  1  0
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5220805

   ---

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: 428.24

Molecular Weight (Monoisotopic): 427.0168

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 97.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.31

CX Basic pKa: ┄

CX LogP: 3.56

CX LogD: 3.51

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.88

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