N-[2-(2-Benzofuran-2-yl-1H-indol-3-yl)-ethyl]-4-pentyl-benzenesulfonamide

ID: ALA179335

Chembl Id: CHEMBL179335

PubChem CID: 11248759

Max Phase: Preclinical

Molecular Formula: C29H30N2O3S

Molecular Weight: 486.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCc1ccc(S(=O)(=O)NCCc2c(-c3cc4ccccc4o3)[nH]c3ccccc23)cc1

Standard InChI:  InChI=1S/C29H30N2O3S/c1-2-3-4-9-21-14-16-23(17-15-21)35(32,33)30-19-18-25-24-11-6-7-12-26(24)31-29(25)28-20-22-10-5-8-13-27(22)34-28/h5-8,10-17,20,30-31H,2-4,9,18-19H2,1H3

Standard InChI Key:  NAGWGZLQLARBPK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA179335

   N-{2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl}-4-pentylbenzene-1-sulfonamide

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: 486.64

Molecular Weight (Monoisotopic): 486.1977

AlogP: 6.83

#Rotatable Bonds: 10

Polar Surface Area: 75.10

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.38

CX Basic pKa:

CX LogP: 6.85

CX LogD: 6.85

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: -0.50

References

1. Weinstein DS, Liu W, Gu Z, Langevine C, Ngu K, Fadnis L, Combs DW, Sitkoff D, Ahmad S, Zhuang S, Chen X, Wang FL, Loughney DA, Atwal KS, Zahler R, Macor JE, Madsen CS, Murugesan N..  (2005)  Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase.,  15  (5): [PMID:15713402] [10.1016/j.bmcl.2004.12.081]

2. Rai G, Joshi N, Jung JE, Liu Y, Schultz L, Yasgar A, Perry S, Diaz G, Zhang Q, Kenyon V, Jadhav A, Simeonov A, Lo EH, van Leyen K, Maloney DJ, Holman TR..  (2014)  Potent and selective inhibitors of human reticulocyte 12/15-lipoxygenase as anti-stroke therapies.,  57  (10): [PMID:24684213] [10.1021/jm401915r]

3. Eleftheriadis N, Neochoritis CG, Leus NG, van der Wouden PE, Dömling A, Dekker FJ..  (2015)  Rational Development of a Potent 15-Lipoxygenase-1 Inhibitor with in Vitro and ex Vivo Anti-inflammatory Properties.,  58  (19): [PMID:26331552] [10.1021/acs.jmedchem.5b01121]

Source

Source(1):

• Scientific Literature