5-[2-(4-Ethyl-phenyl)-vinyl]-1,2,3-trimethoxy-benzene

ID: ALA75284

PubChem CID: 5466706

Max Phase: Preclinical

Molecular Formula: C19H22O3

Molecular Weight: 298.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1

Standard InChI:  InChI=1S/C19H22O3/c1-5-14-6-8-15(9-7-14)10-11-16-12-17(20-2)19(22-4)18(13-16)21-3/h6-13H,5H2,1-4H3/b11-10-

Standard InChI Key:  ATPLLJHVRJWGIN-KHPPLWFESA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.7250   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2500   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2500   -1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  6  1  0
  5  4  2  0
  6  8  1  0
  7  2  1  0
  8  3  2  0
  9  5  1  0
 10  1  1  0
 11  3  1  0
 12  2  1  0
 13 16  2  0
 14  9  1  0
 15  9  2  0
 16 15  1  0
 17 14  2  0
 18 13  1  0
 19 10  1  0
 20 12  1  0
 21 11  1  0
 22 18  1  0
  6  7  2  0
 13 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA75284

   5-[2-(4-Ethyl-phenyl)-vinyl]-1,2,3-trimethoxy-benzene

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: 298.38

Molecular Weight (Monoisotopic): 298.1569

AlogP: 4.45

#Rotatable Bonds: 6

Polar Surface Area: 27.69

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: 0.06

References

1. Cushman M, Nagarathnam D, Gopal D, He HM, Lin CM, Hamel E..  (1992)  Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents.,  35  (12): [PMID:1613753] [10.1021/jm00090a021]

2. Ducki S, Mackenzie G, Lawrence NJ, Snyder JP..  (2005)  Quantitative structure-activity relationship (5D-QSAR) study of combretastatin-like analogues as inhibitors of tubulin assembly.,  48  (2): [PMID:15658859] [10.1021/jm049444m]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays