(S,E)-2-cyano-3-phenyl-N-(1-phenylbutyl)acrylamide

ID: ALA1923258

PubChem CID: 57390775

Max Phase: Preclinical

Molecular Formula: C20H20N2O

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@H](NC(=O)/C(C#N)=C/c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C20H20N2O/c1-2-9-19(17-12-7-4-8-13-17)22-20(23)18(15-21)14-16-10-5-3-6-11-16/h3-8,10-14,19H,2,9H2,1H3,(H,22,23)/b18-14+/t19-/m0/s1

Standard InChI Key:  FYQRTWWWGGEEIU-ZSFFSCSXSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -5.1306  -25.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318  -26.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169  -26.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005  -26.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034  -25.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4187  -24.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904  -24.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744  -25.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615  -24.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2721  -26.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690  -26.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455  -25.3106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5646  -24.0758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326  -24.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834  -25.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837  -26.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988  -26.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127  -26.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070  -25.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912  -24.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357  -24.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517  -23.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548  -22.8356    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
 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
 14 21  1  1
 10 11  3  0
 21 22  1  0
  8 10  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1923258

   (E)-2-cyano-3-phenyl-N-[(1S)-1-phenylbutyl]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: 304.39

Molecular Weight (Monoisotopic): 304.1576

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.98

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.77

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