2-Methoxy-5-[(E)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol

ID: ALA36455

Cas Number: 117048-62-1

PubChem CID: 5386397

Max Phase: Preclinical

Molecular Formula: C18H20O5

Molecular Weight: 316.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: E-Combretastatin A-4 | Trans-Combretastatin A-4 | ND4BUQ9WHL|Trans-Combretastatin A-4|Combretastatin A4, trans-|NSC-609397|E-Combretastatin A-4|UNII-ND4BUQ9WHL|CHEMBL36455|NSC609397|NSC613729|2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol|2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol|2-Methoxy-5-((1E)-2-(3,4,5-trimethoxyphenyl)ethenyl)phenol|Phenol, 2-methoxy-5-((1E)-2-(3,4,5-trimethoxyphenyl)ethenyl)-|117048-62-1|2-Methoxy-5-[(1E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol|PhShow More⌵

Canonical SMILES:  COc1ccc(/C=C/c2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5+

Standard InChI Key:  HVXBOLULGPECHP-AATRIKPKSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    9.1970   -4.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0246   -4.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4387   -3.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0266   -2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1955   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9604   -3.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5500   -4.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7807   -2.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1909   -1.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7839   -4.9162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9589   -4.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2637   -3.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738   -4.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4988   -4.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9060   -4.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7302   -4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1459   -4.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7314   -3.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9086   -3.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9709   -4.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3820   -4.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1400   -5.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
  3 13  1  0
  1  2  2  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
 17 18  2  0
  5  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 15  1  0
  9 10  1  0
 18 21  1  0
  2  3  1  0
 21 22  1  0
  1 11  1  0
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA36455

   E-COMBRETASTATIN A-4

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: 316.35

Molecular Weight (Monoisotopic): 316.1311

AlogP: 3.60

#Rotatable Bonds: 6

Polar Surface Area: 57.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 3.37

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: 0.57

References

1. Pettit GR, Toki BE, Herald DL, Boyd MR, Hamel E, Pettit RK, Chapuis JC..  (1999)  Antineoplastic agents. 410. Asymmetric hydroxylation of trans-combretastatin A-4.,  42  (8): [PMID:10212132] [10.1021/jm9807149]

2. 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]

3. Lawrence NJ, Rennison D, Woo M, McGown AT, Hadfield JA..  (2001)  Antimitotic and cell growth inhibitory properties of combretastatin A-4-like ethers.,  11  (1): [PMID:11140732] [10.1016/s0960-894x(00)00596-5]

4. Pettit GR, Rhodes MR, Herald DL, Hamel E, Schmidt JM, Pettit RK..  (2005)  Antineoplastic agents. 445. Synthesis and evaluation of structural modifications of (Z)- and (E)-combretastatin A-41.,  48  (12): [PMID:15943482] [10.1021/jm0205797]

5. 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]

6. Pettit GR, Lippert JW, Herald DL, Hamel E, Pettit RK..  (2000)  Antineoplastic agents 440. Asymmetric synthesis and evaluation of the combretastatin A-1 SAR probes (1S,2S)- and (1R,2R)-1, 2-dihydroxy- 1-(2',3'-dihydroxy-4'-methoxyphenyl)-2-(3' ',4' ',5' '-trimethoxyphenyl)-ethane.,  63  (7): [PMID:10924176] [10.1021/np0000623]

7. Barbosa EG, Bega LA, Beatriz A, Sarkar T, Hamel E, do Amaral MS, de Lima DP..  (2009)  A diaryl sulfide, sulfoxide, and sulfone bearing structural similarities to combretastatin A-4.,  44  (6): [PMID:19135763] [10.1016/j.ejmech.2008.12.018]

8. Pettit RK, Pettit GR, Hamel E, Hogan F, Moser BR, Wolf S, Pon S, Chapuis JC, Schmidt JM..  (2009)  E-Combretastatin and E-resveratrol structural modifications: antimicrobial and cancer cell growth inhibitory beta-E-nitrostyrenes.,  17  (18): [PMID:19709889] [10.1016/j.bmc.2009.07.076]

9. Pettit GR, Melody N, Thornhill A, Knight JC, Groy TL, Herald CL..  (2009)  Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3: a resveratrol structural modification.,  72  (9): [PMID:19719153] [10.1021/np9002146]

10. Coccetti P, Montano G, Lombardo A, Tripodi F, Orsini F, Pagliarin R..  (2010)  Synthesis and biological evaluation of combretastatin analogs as cell cycle inhibitors of the G1 to S transition in Saccharomyces cerevisiae.,  20  (9): [PMID:20363626] [10.1016/j.bmcl.2010.03.066]

11. Androutsopoulos VP, Ruparelia KC, Papakyriakou A, Filippakis H, Tsatsakis AM, Spandidos DA..  (2011)  Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: structural requirements for potency.,  46  (6): [PMID:21497957] [10.1016/j.ejmech.2011.03.049]

12. PubChem BioAssay data set, 

13. 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]

14. Wong T, Narayanan S, Brown DP, Chen ZS..  (2020)  Synthesis and Cytotoxicity Studies of Stilbene Long-Chain Fatty Acid Conjugates.,  83  (5): [PMID:32243160] [10.1021/acs.jnatprod.0c00027]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays