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

ID: ALA3085014

PubChem CID: 44394815

Max Phase: Preclinical

Molecular Formula: C22H28ClF3N6O4

Molecular Weight: 418.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Cl)nc(N[C@H]2CC[C@H](N)CC2)c(=O)n1CC(=O)Nc1ccc(CN)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C20H27ClN6O2.C2HF3O2/c1-12-18(21)26-19(25-16-8-4-14(23)5-9-16)20(29)27(12)11-17(28)24-15-6-2-13(10-22)3-7-15;3-2(4,5)1(6)7/h2-3,6-7,14,16H,4-5,8-11,22-23H2,1H3,(H,24,28)(H,25,26);(H,6,7)/t14-,16-;

Standard InChI Key:  OIGVPHBTJXCWTC-SWQINVOKSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
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   -2.4833    3.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    3.7958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    2.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6958   -1.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3042   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5458    0.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0250   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -0.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4083   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8333   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417    0.1500    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
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 17 16  1  0
 18 11  2  0
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 20 16  2  0
 21 17  1  0
 22 14  1  6
 23 13  1  0
 26 24  1  1
 25 31  2  0
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 27 21  2  0
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 32 22  1  0
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 34 33  1  0
 35 32  1  0
 36 25  1  0
 10  9  2  0
 34 26  1  0
 30 25  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: 418.93

Molecular Weight (Monoisotopic): 418.1884

AlogP: 1.98

#Rotatable Bonds: 6

Polar Surface Area: 128.06

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.25

CX Basic pKa: 10.20

CX LogP: 0.54

CX LogD: -3.86

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: -1.38

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