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

ID: ALA47426

Cas Number: 134029-49-5

PubChem CID: 5388779

Max Phase: Preclinical

Molecular Formula: C18H20O4

Molecular Weight: 300.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 10Z-3,4,4',5-Tetramethoxystilbene | CHEMBL47426|134029-49-5|1-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene|1-Mtpe|(Z)-1,2,3-Trimethoxy-5-(4-methoxystyryl)benzene|NSC638499|SCHEMBL3834841|(Z)-1,2,3-Trimethoxy-5-(2-(4-methoxyphenyl)ethenyl)benzene|1,2,3-trimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene|cis-3,4,5,4'-tetramethoxystilbene|BDBM50006677|10Z-3,4,4',5-tetramethoxystilbene|NSC-638499|10Z-3,4,4'',5-tetramethoxystilbene|3,4,4'',5-tetramethoxy-(Z)-stilbene|PD181080|(Z) 3,4',5-TETRAMShow More⌵

Canonical SMILES:  COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1

Standard InChI:  InChI=1S/C18H20O4/c1-19-15-9-7-13(8-10-15)5-6-14-11-16(20-2)18(22-4)17(12-14)21-3/h5-12H,1-4H3/b6-5-

Standard InChI Key:  GGFQQRXTLIJXNY-WAYWQWQTSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -3.0931    1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943    0.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    0.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812    1.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529    1.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2338    0.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458   -0.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431   -0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2265   -1.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4887   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825   -0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2223   -2.1670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -2.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3796   -0.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -1.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8091   -0.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5232    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077    1.5332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
 14  9  1  0
  5  7  1  0
 12 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
  3 17  1  0
 17 18  1  0
  8  9  1  0
  2 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  2  0
  1 21  1  0
  2  3  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA47426

   1-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene

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: 300.35

Molecular Weight (Monoisotopic): 300.1362

AlogP: 3.89

#Rotatable Bonds: 6

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.18

References

1. Pettit GR, Toki B, Herald DL, Verdier-Pinard P, Boyd MR, Hamel E, Pettit RK..  (1998)  Antineoplastic agents. 379. Synthesis of phenstatin phosphate.,  41  (10): [PMID:9572894] [10.1021/jm970644q]

2. 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]

3. 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]

4. Cushman M, He HM, Lin CM, Hamel E..  (1993)  Synthesis and evaluation of a series of benzylaniline hydrochlorides as potential cytotoxic and antimitotic agents acting by inhibition of tubulin polymerization.,  36  (19): [PMID:8410995] [10.1021/jm00071a012]

5. Gwaltney SL, Imade HM, Barr KJ, Li Q, Gehrke L, Credo RB, Warner RB, Lee JY, Kovar P, Wang J, Nukkala MA, Zielinski NA, Frost D, Ng SC, Sham HL..  (2001)  Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents.,  11  (7): [PMID:11294380] [10.1016/s0960-894x(01)00098-1]

6. 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]

7. Chang JY, Yang MF, Chang CY, Chen CM, Kuo CC, Liou JP..  (2006)  2-amino and 2'-aminocombretastatin derivatives as potent antimitotic agents.,  49  (21): [PMID:17034147] [10.1021/jm060616k]

8. Zhang W, Go ML..  (2007)  Quinone reductase induction activity of methoxylated analogues of resveratrol.,  42  (6): [PMID:17316918] [10.1016/j.ejmech.2006.12.012]

9. Mateo C, Alvarez R, Pérez-Melero C, Peláez R, Medarde M..  (2007)  Conformationally restricted macrocyclic analogues of combretastatins.,  17  (22): [PMID:17889536] [10.1016/j.bmcl.2007.08.075]

10. Zhang W, Go ML..  (2011)  Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties.,  21  (3): [PMID:21215623] [10.1016/j.bmcl.2010.12.029]

11. PubChem BioAssay data set, 

12. 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]

13. 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]

14. Ahmadi R, Ebrahimzadeh MA..  (2020)  Resveratrol - A comprehensive review of recent advances in anticancer drug design and development.,  200  [PMID:32485531] [10.1016/j.ejmech.2020.112356]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays