(S,E)-2-Cyano-3-(4-nitrophenyl)-N-(1-phenylbutyl)acrylamide

ID: ALA1923256

PubChem CID: 24997031

Max Phase: Preclinical

Molecular Formula: C20H19N3O3

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@H](NC(=O)/C(C#N)=C/c1ccc([N+](=O)[O-])cc1)c1ccccc1

Standard InChI:  InChI=1S/C20H19N3O3/c1-2-6-19(16-7-4-3-5-8-16)22-20(24)17(14-21)13-15-9-11-18(12-10-15)23(25)26/h3-5,7-13,19H,2,6H2,1H3,(H,22,24)/b17-13+/t19-/m0/s1

Standard InChI Key:  HMVYDZAVWQLUPU-UMEYKSNOSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -4.1014  -17.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1026  -18.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3878  -18.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713  -18.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742  -17.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896  -17.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613  -17.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453  -17.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323  -17.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429  -18.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2398  -19.3123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837  -17.6564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355  -16.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966  -17.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6126  -17.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6128  -18.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280  -18.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0419  -18.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361  -17.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204  -17.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935  -16.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1775  -16.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1743  -15.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8193  -18.9093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8200  -19.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5332  -18.4963    0.0000 O   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
 14 21  1  1
 10 11  3  0
 21 22  1  0
  8 10  1  0
 22 23  1  0
  5  6  2  0
  9 12  1  0
  6  1  1  0
 24 25  2  0
 24 26  1  0
  2 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1923256

   (E)-2-cyano-3-(4-nitrophenyl)-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: 349.39

Molecular Weight (Monoisotopic): 349.1426

AlogP: 4.16

#Rotatable Bonds: 7

Polar Surface Area: 96.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.35

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