1,2,3-Trimethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene

ID: ALA86895

PubChem CID: 14256048

Max Phase: Preclinical

Molecular Formula: C17H17NO5

Molecular Weight: 315.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C\c2ccc([N+](=O)[O-])cc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C17H17NO5/c1-21-15-10-13(11-16(22-2)17(15)23-3)5-4-12-6-8-14(9-7-12)18(19)20/h4-11H,1-3H3/b5-4-

Standard InChI Key:  UDXWNMYENXAKPA-PLNGDYQASA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.9875   -6.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -3.5917    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
    4.1250   -2.7625    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
    6.2750   -6.4667    0.0000 O   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
    7.7042   -6.4667    0.0000 O   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
    4.8375   -2.3500    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
    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
    6.9792   -3.5792    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
    2.6917   -3.5917    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
    3.4125   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3 12  2  0
  4 11  1  0
  5  1  1  0
  6  1  1  0
  7  9  2  0
  8  1  2  0
  9 15  1  0
 10  7  1  0
 11 10  2  0
 12 10  1  0
 13  5  2  0
 14  5  1  0
 15 19  1  0
 16  2  1  0
 17  3  1  0
 18  4  1  0
 19 14  2  0
 20 13  1  0
 21 16  1  0
 22 17  1  0
 23 18  1  0
 15 20  2  0
  2  4  2  0
M  CHG  2   1   1   6  -1
M  END

Alternative Forms

1. Parent:

   

   ALA86895

   1,2,3-trimethoxy-5-[(Z)-2-(4-nitrophenyl)ethenyl]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: 315.33

Molecular Weight (Monoisotopic): 315.1107

AlogP: 3.79

#Rotatable Bonds: 6

Polar Surface Area: 70.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.46

Np Likeness Score: -0.24

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. 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]

3. Barnes NG,Parker AW,Ahmed Mal Ullah AA,Ragazzon PA,Hadfield JA.  (2020)  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors.,  28  (19): [PMID:32912434] [10.1016/j.bmc.2020.115684]

Source

Source(1):

• Scientific Literature