(R,E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acrylamide

ID: ALA1923238

PubChem CID: 57390774

Max Phase: Preclinical

Molecular Formula: C19H16BrN3O

Molecular Weight: 382.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cccc(Br)n1)C(=O)N[C@@H]1CCCc2ccccc21

Standard InChI:  InChI=1S/C19H16BrN3O/c20-18-10-4-7-15(22-18)11-14(12-21)19(24)23-17-9-3-6-13-5-1-2-8-16(13)17/h1-2,4-5,7-8,10-11,17H,3,6,9H2,(H,23,24)/b14-11+/t17-/m1/s1

Standard InChI Key:  MRAGYIWQNDNWAW-GWKQRERASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.3527  -18.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3516  -19.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0664  -19.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7828  -19.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7800  -18.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0646  -18.2247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4929  -18.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2089  -18.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9218  -18.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2112  -19.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2143  -20.2790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6378  -18.6231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9187  -17.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6382  -18.2251    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.3508  -18.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7746  -17.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0588  -16.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3417  -17.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7735  -18.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0645  -18.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0639  -19.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7715  -19.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4812  -19.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4783  -18.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
  6  1  1  0
  9 13  2  0
  1  2  2  0
  1 14  1  0
  5  7  1  0
 15 12  1  6
 15 20  1  0
  3  4  2  0
  7  8  2  0
 15 18  1  0
 19 16  1  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
  4  5  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 10 11  3  0
 21 22  2  0
  8 10  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923238

   (E)-3-(6-bromopyridin-2-yl)-2-cyano-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]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: 382.26

Molecular Weight (Monoisotopic): 381.0477

AlogP: 3.94

#Rotatable Bonds: 3

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: 12.12

CX Basic pKa: 0.43

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: -1.17

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