3-(((4-cyclohexyl-6-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)phenol

ID: ALA4876175

PubChem CID: 164628671

Max Phase: Preclinical

Molecular Formula: C18H20F3N3O

Molecular Weight: 351.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1cccc(CNc2nc(C3CCCCC3)cc(C(F)(F)F)n2)c1

Standard InChI:  InChI=1S/C18H20F3N3O/c19-18(20,21)16-10-15(13-6-2-1-3-7-13)23-17(24-16)22-11-12-5-4-8-14(25)9-12/h4-5,8-10,13,25H,1-3,6-7,11H2,(H,22,23,24)

Standard InChI Key:  ATBMDYAQUWUIIO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.4798  -24.4254    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3045  -24.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8958  -23.7135    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.5992  -25.6706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5980  -26.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3125  -26.9102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0286  -26.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0257  -25.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3107  -25.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0211  -24.0190    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8836  -26.9093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1698  -26.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4554  -26.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7424  -26.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0284  -26.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0273  -27.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7461  -28.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4571  -27.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3148  -26.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7410  -26.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7403  -27.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4510  -28.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1669  -27.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -26.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4524  -26.4930    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
  9  2  1  0
  2 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 15 19  1  0
 20 21  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876175

   ---

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: 351.37

Molecular Weight (Monoisotopic): 351.1558

AlogP: 4.86

#Rotatable Bonds: 4

Polar Surface Area: 58.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 3.02

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.92

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