(E)-3-(3'-Hydroxy-4'-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylamide

ID: ALA2285721

PubChem CID: 76312824

Max Phase: Preclinical

Molecular Formula: C19H21NO6

Molecular Weight: 359.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C(/C(N)=O)c2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C19H21NO6/c1-23-15-6-5-11(8-14(15)21)7-13(19(20)22)12-9-16(24-2)18(26-4)17(10-12)25-3/h5-10,21H,1-4H3,(H2,20,22)/b13-7+

Standard InChI Key:  NDAKKEKFVZYOBV-NTUHNPAUSA-N

Molfile:  

     RDKit          2D

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    3.9458  -12.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7609  -12.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598  -11.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6418  -12.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2445  -10.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0644  -10.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8128  -11.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926  -11.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985  -11.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2101  -12.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2629  -11.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4478  -11.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3950  -12.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5070  -13.3471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420  -13.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434  -11.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4569  -12.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117  -12.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970  -13.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928  -13.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7103  -14.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644  -11.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4121  -13.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8624   -9.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2970   -9.1639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0458   -9.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4 11  1  0
  5  7  1  0
  6  5  2  0
  7  9  1  0
  8  2  1  0
  9  3  2  0
 10 13  1  0
 11 12  2  0
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 15  2  1  0
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 17  4  1  0
 18 12  1  0
 19 10  1  0
 20 14  1  0
 21 15  1  0
 22 16  1  0
 23 19  1  0
  8  7  2  0
 10  4  2  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2285721

   (E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)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: 359.38

Molecular Weight (Monoisotopic): 359.1369

AlogP: 2.45

#Rotatable Bonds: 7

Polar Surface Area: 100.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.81

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 0.43

References

1. Liu Y, Li X, Zhao C, Lu Y, Li W, Liu Z, Feng G, Yang L.  (2013)  Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae,  22  (5): [10.1007/s00044-012-0212-x]

Source

Source(1):

• Scientific Literature