(R,E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(2,3-dihydro-1H-inden-1-yl)acrylamide

ID: ALA1923237

PubChem CID: 57390773

Max Phase: Preclinical

Molecular Formula: C18H14BrN3O

Molecular Weight: 368.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cccc(Br)n1)C(=O)N[C@@H]1CCc2ccccc21

Standard InChI:  InChI=1S/C18H14BrN3O/c19-17-7-3-5-14(21-17)10-13(11-20)18(23)22-16-9-8-12-4-1-2-6-15(12)16/h1-7,10,16H,8-9H2,(H,22,23)/b13-10+/t16-/m1/s1

Standard InChI Key:  YDUPEOVBVLLSRR-QSOAKEGCSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -4.4764  -18.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776  -19.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628  -20.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0463  -19.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0492  -18.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646  -18.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3363  -18.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203  -18.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073  -18.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179  -19.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148  -20.4665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913  -18.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105  -17.5758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224  -18.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1910  -18.4126    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1778  -17.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277  -17.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362  -17.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3307  -18.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493  -19.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5732  -19.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767  -18.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5558  -17.8252    0.0000 C   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
 14 12  1  6
  5  7  1  0
  1 15  1  0
 14 19  1  0
  3  4  2  0
  7  8  2  0
 18 16  1  0
 16 17  1  0
 17 14  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 10 11  3  0
 21 22  1  0
  8 10  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923237

   (E)-3-(6-bromopyridin-2-yl)-2-cyano-N-[(1R)-2,3-dihydro-1H-inden-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: 368.23

Molecular Weight (Monoisotopic): 367.0320

AlogP: 3.55

#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: 11.99

CX Basic pKa: 0.43

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: -1.12

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