Acetic acid 4-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenyl ester

ID: ALA87209

PubChem CID: 5388778

Max Phase: Preclinical

Molecular Formula: C19H20O5

Molecular Weight: 328.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C\c2ccc(OC(C)=O)cc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H20O5/c1-13(20)24-16-9-7-14(8-10-16)5-6-15-11-17(21-2)19(23-4)18(12-15)22-3/h5-12H,1-4H3/b6-5-

Standard InChI Key:  SYAOAXJVQVJDPD-WAYWQWQTSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.1250   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -6.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -6.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -2.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  7  1  0
  5 10  1  0
  6  4  2  0
  7  8  1  0
  8  3  2  0
  9  2  1  0
 10 13  1  0
 11  5  2  0
 12  6  1  0
 13 19  2  0
 14  1  1  0
 15  3  1  0
 16  2  1  0
 17 12  1  0
 18 12  2  0
 19 18  1  0
 20 17  2  0
 21  5  1  0
 22 14  1  0
 23 16  1  0
 24 15  1  0
  7  9  2  0
 20 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA87209

   (Z) 4-Acetoxy-3',5'-trimethoxystilbene

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: 328.36

Molecular Weight (Monoisotopic): 328.1311

AlogP: 3.81

#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: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.46

Np Likeness Score: 0.34

References

1. Cushman M, Nagarathnam D, Gopal D, Chakraborti AK, Lin CM, Hamel E..  (1991)  Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization.,  34  (8): [PMID:1875350] [10.1021/jm00112a036]

2. PubChem BioAssay data set, 

3. 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]

4. Uddin R, Naz A, Akhtar N, Zaheer ul Haq.  (2013)  Development of robust QSAR model using rapid overlay of crystal structures (ROCS) based alignment: a test case of Tubulin inhibitors,  22  (7): [10.1007/s00044-012-0327-0]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays