(S,E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-fluorophenyl)ethyl)acrylamide

ID: ALA1923245

PubChem CID: 24992580

Max Phase: Preclinical

Molecular Formula: C17H13BrFN3O

Molecular Weight: 374.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)/C(C#N)=C/c1cccc(Br)n1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C17H13BrFN3O/c1-11(12-5-7-14(19)8-6-12)21-17(23)13(10-20)9-15-3-2-4-16(18)22-15/h2-9,11H,1H3,(H,21,23)/b13-9+/t11-/m0/s1

Standard InChI Key:  QBDAZEDSXHQMAC-GJSJWPQCSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    8.8561   -9.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8549   -9.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5698  -10.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2861   -9.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2832   -9.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5680   -8.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9961   -8.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7121   -9.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4249   -8.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7144   -9.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7175  -10.7906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1409   -9.1348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4218   -7.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8537   -8.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5696   -9.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5699   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2850  -10.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9988   -9.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9931   -9.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2774   -8.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1416   -8.7368    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.8506   -7.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7153  -10.3577    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  9 12  1  0
  6  1  1  0
  9 13  2  0
  1  2  2  0
 12 14  1  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 15  1  0
  2  3  1  0
  1 21  1  0
 10 11  3  0
 14 22  1  1
  8 10  1  0
 18 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923245

   (E)-3-(6-bromopyridin-2-yl)-2-cyano-N-[(1S)-1-(4-fluorophenyl)ethyl]prop-2-enamide

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: 374.21

Molecular Weight (Monoisotopic): 373.0226

AlogP: 3.77

#Rotatable Bonds: 4

Polar Surface Area: 65.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.80

CX Basic pKa: 0.42

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: -1.73

References

1. Peng Z, Pal A, Han D, Wang S, Maxwell D, Levitzki A, Talpaz M, Donato NJ, Bornmann W..  (2011)  Tyrphostin-like compounds with ubiquitin modulatory activity as possible therapeutic agents for multiple myeloma.,  19  (23): [PMID:22036213] [10.1016/j.bmc.2011.09.057]

Source

Source(1):

• Scientific Literature