4-[6-(5-acetyl-2-thienyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropyl-benzamide

ID: ALA3728418

PubChem CID: 117770149

Max Phase: Preclinical

Molecular Formula: C22H18N4O2S

Molecular Weight: 402.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(-c2cn3c(-c4ccc(C(=O)NC5CC5)cc4)cnc3cn2)s1

Standard InChI:  InChI=1S/C22H18N4O2S/c1-13(27)19-8-9-20(29-19)17-12-26-18(10-24-21(26)11-23-17)14-2-4-15(5-3-14)22(28)25-16-6-7-16/h2-5,8-12,16H,6-7H2,1H3,(H,25,28)

Standard InChI Key:  YSTKCRDOQXTSNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114    5.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    5.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2218    4.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593    6.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3455    7.0110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1207    7.7476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084    8.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    2.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259    3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    0.8711    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0548    9.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    9.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4624    1.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1716    2.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9465    0.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
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  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 10 21  2  0
 21 22  1  0
 22 23  2  0
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 24 10  1  0
 25 20  1  0
 26 25  1  0
 20 26  1  0
 23 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728418

   4-[6-(5-acetylthiophen-2-yl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylbenzamide

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: 402.48

Molecular Weight (Monoisotopic): 402.1150

AlogP: 4.22

#Rotatable Bonds: 5

Polar Surface Area: 76.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.90

CX LogP: 2.15

CX LogD: 2.15

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.23

References

1.  (2014)  Nitrogen bicyclic compounds as inhibitors for Scyl1 and Grk5, 

Source

Source(1):

• Patent Bioactivity Data