2-(4-(1-(4-fluorophenyl)-1H-indol-3-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

ID: ALA3354882

Chembl Id: CHEMBL3354882

PubChem CID: 72722778

Max Phase: Preclinical

Molecular Formula: C29H31FN2O2

Molecular Weight: 458.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCCCc1cn(-c3ccc(F)cc3)c3ccccc13)CC2

Standard InChI:  InChI=1S/C29H31FN2O2/c1-33-28-17-21-14-16-31(19-23(21)18-29(28)34-2)15-6-5-7-22-20-32(25-12-10-24(30)11-13-25)27-9-4-3-8-26(22)27/h3-4,8-13,17-18,20H,5-7,14-16,19H2,1-2H3

Standard InChI Key:  GWGRBNDXZUZCBZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3354882

   2-[4-[1-(4-fluorophenyl)indol-3-yl]butyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline

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: 458.58

Molecular Weight (Monoisotopic): 458.2370

AlogP: 6.17

#Rotatable Bonds: 8

Polar Surface Area: 26.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 8.40

CX LogP: 6.66

CX LogD: 5.63

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -0.86

References

1. Abate C, Pati ML, Contino M, Colabufo NA, Perrone R, Niso M, Berardi F..  (2015)  From mixed sigma-2 receptor/P-glycoprotein targeting agents to selective P-glycoprotein modulators: small structural changes address the mechanism of interaction at the efflux pump.,  89  [PMID:25462269] [10.1016/j.ejmech.2014.10.082]

2. Pati ML, Abate C, Contino M, Ferorelli S, Luisi R, Carroccia L, Niso M, Berardi F..  (2015)  Deconstruction of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline moiety to separate P-glycoprotein (P-gp) activity from σ2 receptor affinity in mixed P-gp/σ2 receptor agents.,  89  [PMID:25462276] [10.1016/j.ejmech.2014.11.001]

3. Xie F, Kniess T, Neuber C, Deuther-Conrad W, Mamat C, Lieberman BP, Liu B, Mach RH, Brust P, Steinbach J, Pietzsch J, Jia H.  (2015)  Novel indole-based sigma-2 receptor ligands: synthesis, structureaffinity relationship and antiproliferative activity,  6  (6): [10.1039/C5MD00079C]

4. Wan Y, Li Y, Yan C, Yan M, Tang Z..  (2019)  Indole: A privileged scaffold for the design of anti-cancer agents.,  183  [PMID:31536895] [10.1016/j.ejmech.2019.111691]

Source

Source(1):

• Scientific Literature