4-[6-(3-acetamidophenyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dimethyl-benzamide

ID: ALA3728063

PubChem CID: 117769944

Max Phase: Preclinical

Molecular Formula: C23H21N5O2

Molecular Weight: 399.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(-c2cn3c(-c4ccc(C(=O)N(C)C)cc4)cnc3cn2)c1

Standard InChI:  InChI=1S/C23H21N5O2/c1-15(29)26-19-6-4-5-18(11-19)20-14-28-21(12-25-22(28)13-24-20)16-7-9-17(10-8-16)23(30)27(2)3/h4-14H,1-3H3,(H,26,29)

Standard InChI Key:  LGRUAUDQUJCOMN-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
   -3.6203    2.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2150    1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143    0.7422    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
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    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
    5.7956    8.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    6.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5115    0.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5060   -0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4644   -1.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5427   -1.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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  1 10  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 16  1  0
 19 22  1  0
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 22 24  2  0
 23 25  1  0
 23 26  1  0
 14 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728063

   4-[6-(3-acetamidophenyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dimethylbenzamide

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: 399.45

Molecular Weight (Monoisotopic): 399.1695

AlogP: 3.72

#Rotatable Bonds: 4

Polar Surface Area: 79.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.11

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.63

References

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

Source

Source(1):

• Patent Bioactivity Data