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

ID: ALA78126

Chembl Id: CHEMBL78126

PubChem CID: 11723647

Max Phase: Preclinical

Molecular Formula: C21H22O3

Molecular Weight: 322.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-(3,4,5-Trimethoxyphenethyl)Naphthalene | 2-(3,4,5-Trimethoxyphenethyl)Naphthalene|CHEMBL78126|SCHEMBL21530614

Canonical SMILES:  COc1cc(CCc2ccc3ccccc3c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H22O3/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/h4-7,10-14H,8-9H2,1-3H3

Standard InChI Key:  LXLRBXQETIBITH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA78126

   2-(3,4,5-Trimethoxyphenethyl)Naphthalene

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: 322.40

Molecular Weight (Monoisotopic): 322.1569

AlogP: 4.65

#Rotatable Bonds: 6

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: 5.03

CX LogD: 5.03

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: 0.16

References

1. Medarde M, Ramos AC, Caballero E, Peláez-Lamamié de Clairac R, López JL, Grávalos DG, Feliciano AS..  (1999)  Synthesis and pharmacological activity of diarylindole derivatives. Cytotoxic agents based on combretastatins.,  9  (16): [PMID:10476858] [10.1016/s0960-894x(99)00370-4]

2. Medarde M, Pelaez-Lamamiede Clairac R, Ramos AC, Caballero E, Lopez JL, Gravalos DG, Feliciano AS.  (1995)  Synthesis and pharmacological activity of combretastatin analogues. Naphthylcombretastatins and related compounds,  5  (3): [10.1016/0960-894X(95)00008-H]

3. 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]

4. del Rey B, Ramos AC, Caballero E, Inchaustti A, Yaluff G, Medarde M, Rojas de Arias A, San Feliciano A..  (1999)  Leishmanicidal activity of combretastatin analogues and heteroanalogues.,  9  (18): [PMID:10509921] [10.1016/s0960-894x(99)00453-9]

5. 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]

6. 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]

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

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data