4-((7-(6-methoxynaphthalen-2-yl)benzo[b]thiophen-2-yl)methylamino)butanoic acid

ID: ALA3885357

PubChem CID: 134130292

Max Phase: Preclinical

Molecular Formula: C24H23NO3S

Molecular Weight: 405.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc(-c3cccc4cc(CNCCCC(=O)O)sc34)ccc2c1

Standard InChI:  InChI=1S/C24H23NO3S/c1-28-20-10-9-16-12-18(8-7-17(16)13-20)22-5-2-4-19-14-21(29-24(19)22)15-25-11-3-6-23(26)27/h2,4-5,7-10,12-14,25H,3,6,11,15H2,1H3,(H,26,27)

Standard InChI Key:  WWKMFVBIOIHLKZ-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
   12.3722   -7.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7784   -7.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5956   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0018   -8.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8190   -8.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5908   -9.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6396   -9.7541    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
    7.6477  -10.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423  -10.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9409  -11.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6509  -12.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3535  -11.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6529  -13.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9462  -13.4225    0.0000 C   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
 22 14  2  0
 12 21  1  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 23 21  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885357

   ---

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: 405.52

Molecular Weight (Monoisotopic): 405.1399

AlogP: 5.68

#Rotatable Bonds: 8

Polar Surface Area: 58.56

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.88

CX Basic pKa: 9.81

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -0.43

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