3-((4-(2-ethylphenyl)benzo[b]thiophen-2-yl)methylamino)propanoic acid

ID: ALA3885034

PubChem CID: 134131038

Max Phase: Preclinical

Molecular Formula: C20H21NO2S

Molecular Weight: 339.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-c1cccc2sc(CNCCC(=O)O)cc12

Standard InChI:  InChI=1S/C20H21NO2S/c1-2-14-6-3-4-7-16(14)17-8-5-9-19-18(17)12-15(24-19)13-21-11-10-20(22)23/h3-9,12,21H,2,10-11,13H2,1H3,(H,22,23)

Standard InChI Key:  YLNRUNQIGCWITL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   13.1474   -6.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039   -5.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0091   -5.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7170   -6.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7094   -4.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4182   -5.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256   -5.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2073   -6.1469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.6831   -5.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1953   -4.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5002   -5.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9152   -6.1761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7324   -6.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7020   -3.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4078   -3.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4007   -2.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6888   -2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9825   -2.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9931   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1180   -3.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8232   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9646   -6.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3796   -7.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3667   -6.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  3  4  2  0
  7  4  1  0
  5  6  1  0
  2  5  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13  1  1  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 15 20  1  0
 20 21  1  0
  1 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885034

   ---

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: 339.46

Molecular Weight (Monoisotopic): 339.1293

AlogP: 4.70

#Rotatable Bonds: 7

Polar Surface Area: 49.33

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.29

CX Basic pKa: 9.58

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.92

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