4-[2,6-Dioxo-4-(pentafluoroethyl)-3,6-dihydropyrimidin-1(2H)-yl]-5-methoxy-2-(2-methylphenoxy)benzonitrile

ID: ALA5219673

PubChem CID: 156716035

Max Phase: Preclinical

Molecular Formula: C21H14F5N3O4

Molecular Weight: 467.35

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H14F5N3O4/c1-11-5-3-4-6-14(11)33-15-8-13(16(32-2)7-12(15)10-27)29-18(30)9-17(28-19(29)31)20(22,23)21(24,25)26/h3-9H,1-2H3,(H,28,31)

Standard InChI Key:  QPQFNJFXGFRYKV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.0296   -0.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -0.6175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -1.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4585   -2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -1.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5407    1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551    1.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8262    2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264    3.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389    3.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    3.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551    2.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436    1.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    0.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    3.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -1.4440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.0921    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7443   -3.0921    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2551   -2.0685    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -1.1408    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  8 29  1  0
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  8 31  1  0
  7 32  1  0
  7 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5219673

   ---

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: 467.35

Molecular Weight (Monoisotopic): 467.0904

AlogP: 4.16

#Rotatable Bonds: 5

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: 9.30

CX Basic pKa: ┄

CX LogP: 4.24

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.57

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