(E)-6-(2',6'-dichlorostyryl)-4-methoxy-5-(methoxymethyl)-2H-pyran-2-one

ID: ALA1099213

PubChem CID: 46861772

Max Phase: Preclinical

Molecular Formula: C16H14Cl2O4

Molecular Weight: 341.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCc1c(OC)cc(=O)oc1/C=C/c1c(Cl)cccc1Cl

Standard InChI:  InChI=1S/C16H14Cl2O4/c1-20-9-11-14(22-16(19)8-15(11)21-2)7-6-10-12(17)4-3-5-13(10)18/h3-8H,9H2,1-2H3/b7-6+

Standard InChI Key:  OJAQHGSUGFPQST-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.1390    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918    0.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886    1.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009    1.8957    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5712   -0.5895    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    0.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7205    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353    0.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1419   -0.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583   -0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8596    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443    0.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156   -0.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7130   -1.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972   -2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1395   -1.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -2.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    0.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  2  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
 11 16  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
  3  8  1  0
 12 17  1  0
 17 18  1  0
  4  9  1  0
 18 19  1  0
  4  5  1  0
 13 20  1  0
  9 10  2  0
 20 21  1  0
  2  3  1  0
 15 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099213

   6-[(E)-2-(2,6-dichlorophenyl)ethenyl]-4-methoxy-5-(methoxymethyl)pyran-2-one

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: 341.19

Molecular Weight (Monoisotopic): 340.0269

AlogP: 4.27

#Rotatable Bonds: 5

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -0.02

References

1. Tanaka A, Hamada N, Fujita Y, Itoh T, Nozawa Y, Iinuma M, Ito M..  (2010)  A novel kavalactone derivative protects against H2O2-induced PC12 cell death via Nrf2/ARE activation.,  18  (9): [PMID:20371185] [10.1016/j.bmc.2010.03.034]

Source

Source(1):

• Scientific Literature