4-((7-(4-(trifluoromethyl)phenyl)benzo[b]thiophen-2-yl)methylamino)butanoic acid

ID: ALA3884795

PubChem CID: 134131363

Max Phase: Preclinical

Molecular Formula: C20H18F3NO2S

Molecular Weight: 393.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCCNCc1cc2cccc(-c3ccc(C(F)(F)F)cc3)c2s1

Standard InChI:  InChI=1S/C20H18F3NO2S/c21-20(22,23)15-8-6-13(7-9-15)17-4-1-3-14-11-16(27-19(14)17)12-24-10-2-5-18(25)26/h1,3-4,6-9,11,24H,2,5,10,12H2,(H,25,26)

Standard InChI Key:  RUXOXYWHXQUSCO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  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
    8.3558  -10.9789    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
    8.3574  -11.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505  -12.2060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0659  -12.2033    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3494  -12.6128    0.0000 F   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
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884795

   ---

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: 393.43

Molecular Weight (Monoisotopic): 393.1010

AlogP: 5.54

#Rotatable Bonds: 7

Polar Surface Area: 49.33

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.88

CX Basic pKa: 9.81

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.82

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