4-(furan-2-yl)-N-(3-methoxybenzyl)-6-(trifluoromethyl)pyrimidin-2-amine

ID: ALA4869460

PubChem CID: 164618926

Max Phase: Preclinical

Molecular Formula: C17H14F3N3O2

Molecular Weight: 349.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2nc(-c3ccco3)cc(C(F)(F)F)n2)c1

Standard InChI:  InChI=1S/C17H14F3N3O2/c1-24-12-5-2-4-11(8-12)10-21-16-22-13(14-6-3-7-25-14)9-15(23-16)17(18,19)20/h2-9H,10H2,1H3,(H,21,22,23)

Standard InChI Key:  NUJUSPHCPXXUMH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.9331   -9.5082    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7581   -9.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3493   -8.7958    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0526  -10.7539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0514  -11.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7662  -11.9942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4826  -11.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4798  -10.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7644  -10.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1983  -11.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2858  -12.8101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0930  -12.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5044  -12.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9514  -11.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4751   -9.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3366  -11.9933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6225  -11.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9077  -11.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1943  -11.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4800  -11.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4789  -12.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1981  -13.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9094  -12.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7661  -11.5747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7671  -10.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  7 10  1  0
  9  2  1  0
  2 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 20 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4869460

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 349.31

Molecular Weight (Monoisotopic): 349.1038

AlogP: 4.38

#Rotatable Bonds: 5

Polar Surface Area: 60.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.30

CX LogP: 4.13

CX LogD: 4.13

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.67

References

1. Dolšak A, Šribar D, Scheffler A, Grabowski M, Švajger U, Gobec S, Holze J, Weindl G, Wolber G, Sova M..  (2021)  Further hit optimization of 6-(trifluoromethyl)pyrimidin-2-amine based TLR8 modulators: Synthesis, biological evaluation and structure-activity relationships.,  225  [PMID:34488023] [10.1016/j.ejmech.2021.113809]

Source

Source(1):

• Scientific Literature