2-[3-(4-Amino-cyclohexylamino)-5-chloro-6-methyl-2-oxo-2H-pyrazin-1-yl]-N-[2-(1H-imidazol-4-yl)-ethyl]-acetamide TFA

ID: ALA3085010

PubChem CID: 44394710

Max Phase: Preclinical

Molecular Formula: C20H27ClF3N7O4

Molecular Weight: 407.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Cl)nc(N[C@H]2CC[C@H](N)CC2)c(=O)n1CC(=O)NCCc1c[nH]cn1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C18H26ClN7O2.C2HF3O2/c1-11-16(19)25-17(24-13-4-2-12(20)3-5-13)18(28)26(11)9-15(27)22-7-6-14-8-21-10-23-14;3-2(4,5)1(6)7/h8,10,12-13H,2-7,9,20H2,1H3,(H,21,23)(H,22,27)(H,24,25);(H,6,7)/t12-,13-;

Standard InChI Key:  BIHSBTZFUNZNDJ-UBRLZZGHSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.4333    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    3.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500    3.8583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    1.8500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083    2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9333   -0.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2208   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -0.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0917   -0.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9292   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -2.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    1.0375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -0.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -1.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958    0.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0625    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  1  1  0
  6  1  1  0
  7  2  1  0
  9 12  1  0
 10 11  1  0
 11  8  1  0
 12 13  2  0
 13  8  1  0
 14 17  1  0
 15 10  1  0
 16  8  1  0
 17 27  1  0
 18 22  1  0
 19 14  2  0
 20 16  1  0
 21 11  2  0
 22 17  2  0
 23 12  1  0
 24 20  2  0
 25 20  1  0
 26 15  1  6
 27 29  1  0
 28 13  1  0
 29 25  1  0
 31 30  1  1
 31 35  1  0
 32 26  1  0
 33 26  1  0
 34 33  1  0
 35 32  1  0
 10  9  2  0
 34 31  1  0
 18 19  1  0
M  END

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: 407.91

Molecular Weight (Monoisotopic): 407.1837

AlogP: 0.97

#Rotatable Bonds: 7

Polar Surface Area: 130.72

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: 10.15

CX LogP: -0.68

CX LogD: -3.30

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.25

References

1. Hopkins C, Neuenschwander K, Scotese A, Jackson S, Nieduzak T, Pauls H, Liang G, Sides K, Cramer D, Cairns J, Maignan S, Mathieu M..  (2004)  Novel pyrazinone inhibitors of mast cell tryptase: synthesis and SAR evaluation.,  14  (19): [PMID:15341931] [10.1016/j.bmcl.2004.07.051]

Source

Source(1):

• Scientific Literature