2-(4-((7-(2-ethylphenyl)benzo[b]thiophen-2-yl)methylamino)phenyl)acetic acid

ID: ALA3885195

PubChem CID: 134131470

Max Phase: Preclinical

Molecular Formula: C25H23NO2S

Molecular Weight: 401.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-c1cccc2cc(CNc3ccc(CC(=O)O)cc3)sc12

Standard InChI:  InChI=1S/C25H23NO2S/c1-2-18-6-3-4-8-22(18)23-9-5-7-19-15-21(29-25(19)23)16-26-20-12-10-17(11-13-20)14-24(27)28/h3-13,15,26H,2,14,16H2,1H3,(H,27,28)

Standard InChI Key:  RNHYCLDILVZJFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    9.0616   -8.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8328   -8.3732    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3248   -7.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1443   -7.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5550   -7.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8685   -7.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0721   -7.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3597   -6.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6485   -7.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6450   -8.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3504   -8.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3504   -9.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0622   -9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0611  -10.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3530  -10.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6450  -10.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6383   -9.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7700   -9.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4777   -9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3722   -7.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7771   -7.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5936   -7.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0054   -7.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5947   -6.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7797   -6.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8225   -7.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2297   -7.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0469   -7.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8197   -8.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  3  2  0
  7  6  1  0
  1  7  2  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
  1 11  1  0
 11 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
 13 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885195

   ---

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: 401.53

Molecular Weight (Monoisotopic): 401.1449

AlogP: 6.37

#Rotatable Bonds: 7

Polar Surface Area: 49.33

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.93

CX Basic pKa: 3.37

CX LogP: 6.13

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.72

References

1. Hur W, Rosen H, Gray NS..  (2017)  A benzo[b]thiophene-based selective type 4 S1P receptor agonist.,  27  (1): [PMID:27894870] [10.1016/j.bmcl.2016.11.050]

Source

Source(1):

• Scientific Literature