1,2,3-Trimethoxy-5-styryl-benzene

ID: ALA87162

Chembl Id: CHEMBL87162

Cas Number: 74809-44-2

PubChem CID: 5388756

Max Phase: Preclinical

Molecular Formula: C17H18O3

Molecular Weight: 270.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C\c2ccccc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C17H18O3/c1-18-15-11-14(12-16(19-2)17(15)20-3)10-9-13-7-5-4-6-8-13/h4-12H,1-3H3/b10-9-

Standard InChI Key:  CMQGCWMEXQRWSS-KTKRTIGZSA-N

Alternative Forms

1. Parent:

   

   ALA87162

   (Z)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: 270.33

Molecular Weight (Monoisotopic): 270.1256

AlogP: 3.88

#Rotatable Bonds: 5

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: 3.84

CX LogD: 3.84

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.77

Np Likeness Score: 0.22

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]

5. Mamidyala SK, Ramu S, Huang JX, Robertson AA, Cooper MA..  (2013)  Efficient synthesis of anacardic acid analogues and their antibacterial activities.,  23  (6): [PMID:23416004] [10.1016/j.bmcl.2013.01.074]

6. Roman BI, De Coen LM, Thérèse F C Mortier S, De Ryck T, Vanhoecke BW, Katritzky AR, Bracke ME, Stevens CV..  (2013)  Design, synthesis and structure-activity relationships of some novel, highly potent anti-invasive (E)- and (Z)-stilbenes.,  21  (17): [PMID:23867387] [10.1016/j.bmc.2013.06.048]

7.  (2018)  Inhibitors of sox18 protein activity for treating angiogenesis- and/or lymphangiogenesis-related diseases, 

8. 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(3):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data