(S,E)-Methyl 3-(3-(6-bromopyridin-2-yl)-2-cyanoacrylamido)-3-phenylpropanoate

ID: ALA1923247

PubChem CID: 57401278

Max Phase: Preclinical

Molecular Formula: C19H16BrN3O3

Molecular Weight: 414.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@H](NC(=O)/C(C#N)=C/c1cccc(Br)n1)c1ccccc1

Standard InChI:  InChI=1S/C19H16BrN3O3/c1-26-18(24)11-16(13-6-3-2-4-7-13)23-19(25)14(12-21)10-15-8-5-9-17(20)22-15/h2-10,16H,11H2,1H3,(H,23,25)/b14-10+/t16-/m0/s1

Standard InChI Key:  CQJCYXYDSUGERD-DKGMDFAASA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    9.3861  -15.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3849  -16.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0997  -17.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8162  -16.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8133  -15.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0979  -15.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5262  -15.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2422  -15.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9552  -15.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -16.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2477  -17.5040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6712  -15.8481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9520  -14.6133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3841  -15.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1001  -15.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1003  -16.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8155  -17.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5294  -16.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5236  -15.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8079  -15.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715  -15.4501    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.3810  -14.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0939  -14.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0908  -13.3677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8099  -14.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3748  -12.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 22 23  1  0
  5  6  2  0
 23 24  1  0
  9 12  1  0
 23 25  2  0
  6  1  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923247

   methyl (3S)-3-[[(E)-3-(6-bromopyridin-2-yl)-2-cyanoprop-2-enoyl]amino]-3-phenylpropanoate

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: 414.26

Molecular Weight (Monoisotopic): 413.0375

AlogP: 3.17

#Rotatable Bonds: 6

Polar Surface Area: 92.08

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.72

CX Basic pKa: 0.42

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: -1.04

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