Ethyl (E)-3-(6-((E)-4-Methoxystyryl)benzo[d][1,3]dioxol-5-yl)-acrylate

ID: ALA4097570

PubChem CID: 137660393

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/c1cc2c(cc1/C=C/c1ccc(OC)cc1)OCO2

Standard InChI:  InChI=1S/C21H20O5/c1-3-24-21(22)11-8-17-13-20-19(25-14-26-20)12-16(17)7-4-15-5-9-18(23-2)10-6-15/h4-13H,3,14H2,1-2H3/b7-4+,11-8+

Standard InChI Key:  LRLHITSDAZIIKC-VCABWLAWSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.8289  -12.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1239  -12.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1239  -11.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8289  -13.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5380  -12.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2235   -9.9406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7434  -10.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2235  -11.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0008  -11.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0008  -10.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7057   -9.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4148  -10.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4148  -11.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7057  -11.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1239   -9.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1239   -8.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8289   -8.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8289   -7.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5380   -7.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2471   -7.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2471   -8.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5380   -8.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9520   -7.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9520   -6.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2471  -12.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2471  -13.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 10 11  2  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 23 24  1  0
 20 23  1  0
 12 15  1  0
  3 13  1  0
 25 26  1  0
  5 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097570

   ---

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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 4.17

#Rotatable Bonds: 6

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.68

CX LogD: 4.68

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 0.27

References

1. Chen PC, Tsai WJ, Ueng YF, Tzeng TT, Chen HL, Zhu PR, Huang CH, Shiao YJ, Li WT..  (2017)  Neuroprotective and Antineuroinflammatory Effects of Hydroxyl-Functionalized Stilbenes and 2-Arylbenzo[b]furans.,  60  (9): [PMID:28459572] [10.1021/acs.jmedchem.7b00376]

Source

Source(1):

• Scientific Literature