4-((7-(biphenyl-3-yl)benzo[b]thiophen-2-yl)methylamino)butanoic acid

ID: ALA3884809

PubChem CID: 134130066

Max Phase: Preclinical

Molecular Formula: C25H23NO2S

Molecular Weight: 401.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCCNCc1cc2cccc(-c3cccc(-c4ccccc4)c3)c2s1

Standard InChI:  InChI=1S/C25H23NO2S/c27-24(28)13-6-14-26-17-22-16-21-11-5-12-23(25(21)29-22)20-10-4-9-19(15-20)18-7-2-1-3-8-18/h1-5,7-12,15-16,26H,6,13-14,17H2,(H,27,28)

Standard InChI Key:  WAKDBPOCXFMNBD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
   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
    7.6450  -10.5688    0.0000 C   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
    6.9391  -10.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325  -10.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5271  -10.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5302  -11.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2447  -12.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9472  -11.7931    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
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 11 10  2  0
  1 11  1  0
 11 12  1  0
 13 12  2  0
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 15 14  2  0
 22 15  1  0
 12 23  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884809

   ---

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: 401.53

Molecular Weight (Monoisotopic): 401.1449

AlogP: 6.19

#Rotatable Bonds: 8

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: 3.36

CX LogD: 3.37

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -0.51

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