(S,E)-2-cyano-3-(1,8-naphthyridin-2-yl)-N-(1-phenylbutyl)acrylamide

ID: ALA4472933

PubChem CID: 118019213

Max Phase: Preclinical

Molecular Formula: C22H20N4O

Molecular Weight: 356.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC[C@H](NC(=O)/C(C#N)=C/c1ccc2cccnc2n1)c1ccccc1

Standard InChI:  InChI=1S/C22H20N4O/c1-2-7-20(16-8-4-3-5-9-16)26-22(27)18(15-23)14-19-12-11-17-10-6-13-24-21(17)25-19/h3-6,8-14,20H,2,7H2,1H3,(H,26,27)/b18-14+/t20-/m0/s1

Standard InChI Key:  JXRQVCRRGBZHRU-GJPUVDBCSA-N

Molfile:  

 
     RDKit          2D

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    6.6786   -4.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6757   -3.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603   -3.4372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -3.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1046   -3.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8175   -3.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5335   -3.8355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8144   -2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1077   -4.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1108   -5.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464   -3.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9624   -3.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2433   -2.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9562   -2.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9627   -4.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6778   -5.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3917   -4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3859   -3.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6702   -3.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6722   -2.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473   -4.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2496   -3.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370   -3.4387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232   -4.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365   -5.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 23  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  6 10  1  0
 10 11  3  0
  8 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
 13 16  2  0
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 17 18  2  0
 18 19  1  0
 19 20  2  0
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 15 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
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 26 27  1  0
 27 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4472933

   (S,E)-2-Cyano-3-(1,8-naphthyridin-2-yl)-N-(1-phenylbutyl)acrylamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 356.43

Molecular Weight (Monoisotopic): 356.1637

AlogP: 4.19

#Rotatable Bonds: 6

Polar Surface Area: 78.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.64

CX Basic pKa: 0.41

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.98

References

1.  (2016)  Deubiquitinase inhibitors and methods for use of the same, 

Source

Source(1):

• Patent Bioactivity Data