4-{2-[3-(4-Amino-cyclohexylamino)-5-chloro-6-methyl-2-oxo-2H-pyrazin-1-yl]-acetylamino}-benzamide TFA

ID: ALA3085007

PubChem CID: 44394597

Max Phase: Preclinical

Molecular Formula: C22H26ClF3N6O5

Molecular Weight: 432.91

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H25ClN6O3.C2HF3O2/c1-11-17(21)26-19(25-15-8-4-13(22)5-9-15)20(30)27(11)10-16(28)24-14-6-2-12(3-7-14)18(23)29;3-2(4,5)1(6)7/h2-3,6-7,13,15H,4-5,8-10,22H2,1H3,(H2,23,29)(H,24,28)(H,25,26);(H,6,7)/t13-,15-;

Standard InChI Key:  WHDXCQNRGXFBBC-IOJSEOPQSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
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   -2.6254    3.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    3.7595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    1.9691    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    1.7572    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    1.9691    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8403   -1.5329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4195    0.9471    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2260    0.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240   -0.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0236   -0.2368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447   -1.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506   -1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136    0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8676   -1.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6817    0.1204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9713   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2485    0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9713   -1.1092    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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 14 10  1  0
 15  8  1  0
 16 15  1  0
 17 20  1  0
 18 16  1  0
 19 11  2  0
 20 24  1  0
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 22 17  2  0
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 24 30  2  0
 25 31  1  0
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 27 18  1  0
 28 14  1  6
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 30 27  1  0
 31 27  2  0
 33 32  1  1
 33 37  1  0
 34 28  1  0
 35 28  1  0
 36 35  1  0
 37 34  1  0
 10  9  2  0
 36 33  1  0
 25 20  2  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: 432.91

Molecular Weight (Monoisotopic): 432.1677

AlogP: 1.62

#Rotatable Bonds: 6

Polar Surface Area: 145.13

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.19

CX Basic pKa: 10.15

CX LogP: 0.27

CX LogD: -2.30

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -1.55

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