4-((7-(4-tert-butylphenyl)benzo[b]thiophen-2-yl)methylamino)butanoic acid

ID: ALA3884888

PubChem CID: 134131169

Max Phase: Preclinical

Molecular Formula: C23H27NO2S

Molecular Weight: 381.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(-c2cccc3cc(CNCCCC(=O)O)sc23)cc1

Standard InChI:  InChI=1S/C23H27NO2S/c1-23(2,3)18-11-9-16(10-12-18)20-7-4-6-17-14-19(27-22(17)20)15-24-13-5-8-21(25)26/h4,6-7,9-12,14,24H,5,8,13,15H2,1-3H3,(H,25,26)

Standard InChI Key:  RZNZHOIMGLOINS-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
    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
   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
    8.3552  -11.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6486  -12.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0640  -12.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3494  -12.6087    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
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884888

   ---

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: 381.54

Molecular Weight (Monoisotopic): 381.1763

AlogP: 5.82

#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: 3.26

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -0.71

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