(1s,4s)-4-(4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)-1H-imidazol-1-yl)cyclohexanol

ID: ALA4166018

Max Phase: Preclinical

Molecular Formula: C20H21FN4O2

Molecular Weight: 368.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nccc(-c2c(-c3ccc(F)cc3)ncn2[C@H]2CC[C@@H](O)CC2)n1

Standard InChI:  InChI=1S/C20H21FN4O2/c1-27-20-22-11-10-17(24-20)19-18(13-2-4-14(21)5-3-13)23-12-25(19)15-6-8-16(26)9-7-15/h2-5,10-12,15-16,26H,6-9H2,1H3/t15-,16+

Standard InChI Key:  ZQUSFAUAYSEREK-IYBDPMFKSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.9576  -12.3445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9564  -13.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6645  -13.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3741  -13.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3713  -12.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6627  -11.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0830  -13.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1697  -14.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9693  -14.5499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3768  -13.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8290  -13.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5642  -14.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7859  -14.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1798  -15.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3508  -16.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1332  -16.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7359  -15.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9978  -12.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7761  -12.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9458  -11.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402  -10.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5619  -11.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3892  -11.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2484  -13.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5410  -13.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7451  -16.5717    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5118  -10.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
  4  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  8 12  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 11  1  1
  2 24  1  0
 24 25  1  0
 15 26  1  0
 21 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4166018

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 368.41

Molecular Weight (Monoisotopic): 368.1649

AlogP: 3.63

#Rotatable Bonds: 4

Polar Surface Area: 73.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.45

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.84

References

1. Bistrović A, Krstulović L, Harej A, Grbčić P, Sedić M, Koštrun S, Pavelić SK, Bajić M, Raić-Malić S..  (2018)  Design, synthesis and biological evaluation of novel benzimidazole amidines as potent multi-target inhibitors for the treatment of non-small cell lung cancer.,  143  [PMID:29133046] [10.1016/j.ejmech.2017.10.061]

Source

Source(1):

• Scientific Literature