US8759537, 82

ID: ALA3694571

PubChem CID: 56839755

Max Phase: Preclinical

Molecular Formula: C31H35Cl2F5N6O3

Molecular Weight: 705.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CCCN1C(=O)NCc1ccc(Cl)c(Nc2nc3cc(C(=O)N[C@H]4CC[C@H](C(F)(F)F)CC4)c(OCC(F)F)cc3n2C)c1Cl

Standard InChI:  InChI=1S/C31H35Cl2F5N6O3/c1-16-4-3-11-44(16)30(46)39-14-17-5-10-21(32)27(26(17)33)42-29-41-22-12-20(24(47-15-25(34)35)13-23(22)43(29)2)28(45)40-19-8-6-18(7-9-19)31(36,37)38/h5,10,12-13,16,18-19,25H,3-4,6-9,11,14-15H2,1-2H3,(H,39,46)(H,40,45)(H,41,42)/t16?,18-,19-

Standard InChI Key:  VPIIQLBGLJOXHS-YGXOWLSWSA-N

Molfile:  

     RDKit          2D

 47 51  0  0  1  0  0  0  0  0999 V2000
   11.2824    1.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6600    0.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0866    0.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0866   -1.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6600   -1.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8002   -0.5024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2994   -0.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6976    0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5508   -1.8063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -1.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3014   -3.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0560   -4.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3105   -5.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105   -5.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -6.7548    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -4.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -4.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    9.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   10.3518    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676   10.3508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065   10.9511    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2387    0.8917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -3.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1979   -2.0783    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 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  1  0
 23 24  2  0
 23 25  1  0
 26 25  1  1
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 26  1  0
 29 32  1  6
 32 33  1  0
 32 34  1  0
 32 35  1  0
 22 36  2  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 36 42  1  0
 42 43  2  0
 43 20  1  0
 43 44  1  0
 44 18  1  0
 44 45  1  0
 16 46  2  0
 46 11  1  0
 46 47  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694571

   2-[2,6-dichloro-3-[[(2-methylpyrrolidine-1-carbonyl)amino]methyl]anilino]-6-(2,2-difluoroethoxy)-1-methyl-N-[4-(trifluoromethyl)cyclohexyl]benzimidazole-5-carboxamide

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: 705.56

Molecular Weight (Monoisotopic): 704.2068

AlogP: 7.81

#Rotatable Bonds: 9

Polar Surface Area: 100.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.41

CX Basic pKa: 5.54

CX LogP: 6.44

CX LogD: 6.44

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.20

Np Likeness Score: -1.45

References

1.  (2014)  3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents, 

Source

Source(1):

• BindingDB Database