2-amino-3-((7-(2-ethylphenyl)benzo[b]thiophen-2-yl)methylamino)propanoic acid

ID: ALA3885229

PubChem CID: 134131188

Max Phase: Preclinical

Molecular Formula: C20H22N2O2S

Molecular Weight: 354.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-c1cccc2cc(CNCC(N)C(=O)O)sc12

Standard InChI:  InChI=1S/C20H22N2O2S/c1-2-13-6-3-4-8-16(13)17-9-5-7-14-10-15(25-19(14)17)11-22-12-18(21)20(23)24/h3-10,18,22H,2,11-12,21H2,1H3,(H,23,24)

Standard InChI Key:  JWSRNECCLVFGPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  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
   12.3741   -7.0141    0.0000 C   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
   12.7795   -7.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5966   -7.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0020   -8.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3676   -8.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0084   -7.0216    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
  5  6  1  0
  7  3  2  0
  8  7  1  0
  1  8  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  1 12  1  0
 12 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 13 18  1  0
 14 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885229

   ---

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: 354.48

Molecular Weight (Monoisotopic): 354.1402

AlogP: 3.63

#Rotatable Bonds: 7

Polar Surface Area: 75.35

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.34

CX Basic pKa: 9.29

CX LogP: 1.60

CX LogD: 1.57

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.38

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