1-((7-(2-ethylphenyl)benzo[b]thiophen-2-yl)methyl)azetidine-3-carboxylic acid

ID: ALA3885035

PubChem CID: 134131039

Max Phase: Preclinical

Molecular Formula: C21H21NO2S

Molecular Weight: 351.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-c1cccc2cc(CN3CC(C(=O)O)C3)sc12

Standard InChI:  InChI=1S/C21H21NO2S/c1-2-14-6-3-4-8-18(14)19-9-5-7-15-10-17(25-20(15)19)13-22-11-16(12-22)21(23)24/h3-10,16H,2,11-13H2,1H3,(H,23,24)

Standard InChI Key:  NRMSYCGUYUEQRF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  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
    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
   12.3427   -6.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1340   -6.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3445   -6.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5450   -5.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3622   -5.3124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1387   -4.6006    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
  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
 13 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 22  5  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885035

   ---

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: 351.47

Molecular Weight (Monoisotopic): 351.1293

AlogP: 4.65

#Rotatable Bonds: 5

Polar Surface Area: 40.54

Molecular Species: ZWITTERION

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: 8.61

CX LogP: 2.32

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.80

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