N-(4-Hydroxyphenethyl)-3-(pyridin-4-yl)-3-p-tolylacrylamide

ID: ALA2272421

PubChem CID: 76308870

Max Phase: Preclinical

Molecular Formula: C23H22N2O2

Molecular Weight: 358.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(/C(=C/C(=O)NCCc2ccc(O)cc2)c2ccncc2)cc1

Standard InChI:  InChI=1S/C23H22N2O2/c1-17-2-6-19(7-3-17)22(20-11-13-24-14-12-20)16-23(27)25-15-10-18-4-8-21(26)9-5-18/h2-9,11-14,16,26H,10,15H2,1H3,(H,25,27)/b22-16-

Standard InChI Key:  JBFQZYPZKWIPTI-JWGURIENSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.4618  -13.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4607  -13.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1687  -14.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8784  -13.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1669  -12.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5817  -12.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2910  -13.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9971  -12.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7064  -13.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9940  -11.8954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786  -11.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2866  -11.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838  -10.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5740  -10.2711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8656  -10.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8718  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4125  -12.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1218  -13.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8279  -12.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5344  -13.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2400  -12.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2374  -11.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5232  -11.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8204  -11.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9430  -11.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526  -14.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272421

   (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-(4-methylphenyl)-3-pyridin-4-ylprop-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: 358.44

Molecular Weight (Monoisotopic): 358.1681

AlogP: 3.89

#Rotatable Bonds: 6

Polar Surface Area: 62.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: 4.78

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -0.33

References

1. Xiao Y, Yang X, Li B, Yuan H, Wan S, Xu Y, Qin Z..  (2011)  Design, synthesis and antifungal/insecticidal evaluation of novel cinnamide derivatives.,  16  (11): [PMID:22027951] [10.3390/molecules16118945]

Source

Source(1):

• Scientific Literature