(S,E)-N-(1-(3,5-Bis(trifluoromethyl)phenyl)ethyl)-3-(6-bromopyridin-2-yl)-2-cyanoacrylamide

ID: ALA1923246

PubChem CID: 57396066

Max Phase: Preclinical

Molecular Formula: C19H12BrF6N3O

Molecular Weight: 492.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)/C(C#N)=C/c1cccc(Br)n1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C19H12BrF6N3O/c1-10(11-5-13(18(21,22)23)8-14(6-11)19(24,25)26)28-17(30)12(9-27)7-15-3-2-4-16(20)29-15/h2-8,10H,1H3,(H,28,30)/b12-7+/t10-/m0/s1

Standard InChI Key:  OHQKJWNLDVIVTH-QVIVLVACSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.9973  -17.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984  -18.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2836  -18.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5672  -18.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700  -17.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2854  -16.7664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571  -16.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411  -17.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4282  -16.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388  -17.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357  -18.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878  -17.1647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313  -15.9299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008  -16.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168  -17.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170  -17.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4322  -18.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461  -17.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1403  -17.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245  -16.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7118  -16.7668    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.9976  -15.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349  -19.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218  -19.6340    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507  -19.6293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292  -20.0417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517  -16.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5692  -17.1392    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457  -15.9070    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625  -16.3125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 17 23  1  0
  5  6  2  0
 23 24  1  0
  9 12  1  0
 23 25  1  0
  6  1  1  0
 23 26  1  0
  9 13  2  0
 19 27  1  0
  1  2  2  0
 27 28  1  0
 12 14  1  0
 27 29  1  0
  5  7  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923246

   (E)-N-[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-3-(6-bromopyridin-2-yl)-2-cyanoprop-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: 492.22

Molecular Weight (Monoisotopic): 491.0068

AlogP: 5.67

#Rotatable Bonds: 4

Polar Surface Area: 65.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.98

CX Basic pKa: 0.42

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: -1.37

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