2-[(Z)-2-(3,4,5-Trimethoxy-phenyl)-vinyl]-naphthalene

ID: ALA85065

Chembl Id: CHEMBL85065

PubChem CID: 9973296

Max Phase: Preclinical

Molecular Formula: C21H20O3

Molecular Weight: 320.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Naphtylcombretastatin | naphtylcombretastatin|CHEMBL85065|SCHEMBL20332776|BDBM50159583|2-[(Z)-2-(3,4,5-Trimethoxy-phenyl)-vinyl]-naphthalene

Canonical SMILES:  COc1cc(/C=C\c2ccc3ccccc3c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H20O3/c1-22-19-13-16(14-20(23-2)21(19)24-3)9-8-15-10-11-17-6-4-5-7-18(17)12-15/h4-14H,1-3H3/b9-8-

Standard InChI Key:  GOOTUFTVCKSZRA-HJWRWDBZSA-N

Alternative Forms

1. Parent:

   

   ALA85065

   NAPHTHYLCOMBRETASTATIN

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: 320.39

Molecular Weight (Monoisotopic): 320.1412

AlogP: 5.04

#Rotatable Bonds: 5

Polar Surface Area: 27.69

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.18

References

1. Maya AB, del Rey B, Lamamie de Clairac RP, Caballero E, Barasoain I, Andreu JM, Medarde M..  (2000)  Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4.,  10  (22): [PMID:11086727] [10.1016/s0960-894x(00)00506-0]

2. Pérez-Melero C, Maya AB, del Rey B, Peláez R, Caballero E, Medarde M..  (2004)  A new family of quinoline and quinoxaline analogues of combretastatins.,  14  (14): [PMID:15203159] [10.1016/j.bmcl.2004.04.098]

3. Maya AB, Pérez-Melero C, Mateo C, Alonso D, Fernández JL, Gajate C, Mollinedo F, Peláez R, Caballero E, Medarde M..  (2005)  Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety.,  48  (2): [PMID:15658869] [10.1021/jm0310737]

4. Alvarez C, Alvarez R, Corchete P, Pérez-Melero C, Peláez R, Medarde M..  (2007)  Synthesis and biological activity of naphthalene analogues of phenstatins: naphthylphenstatins.,  17  (12): [PMID:17434303] [10.1016/j.bmcl.2007.03.082]

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. Makar S, Saha T, Singh SK..  (2019)  Naphthalene, a versatile platform in medicinal chemistry: Sky-high perspective.,  161  [PMID:30366253] [10.1016/j.ejmech.2018.10.018]

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

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data