2-methyl-3-((5-(naphthalen-2-yl)benzo[b]thiophen-2-yl)methylamino)propanoic acid

ID: ALA3884995

PubChem CID: 134130662

Max Phase: Preclinical

Molecular Formula: C23H21NO2S

Molecular Weight: 375.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CNCc1cc2cc(-c3ccc4ccccc4c3)ccc2s1)C(=O)O

Standard InChI:  InChI=1S/C23H21NO2S/c1-15(23(25)26)13-24-14-21-12-20-11-19(8-9-22(20)27-21)18-7-6-16-4-2-3-5-17(16)10-18/h2-12,15,24H,13-14H2,1H3,(H,25,26)

Standard InChI Key:  PAIIIKVRFZNHMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.1395   -4.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5580   -4.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642   -5.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9714   -4.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6807   -5.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6860   -6.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3939   -6.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3862   -4.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9645   -3.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2492   -3.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -4.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8272   -3.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1281   -4.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0950   -5.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1024   -6.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8842   -6.2708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3599   -5.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8722   -4.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1771   -5.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5921   -6.2999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4093   -6.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8243   -6.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6414   -6.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0564   -7.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4221   -7.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0436   -6.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  5  6  1  0
  7  6  1  0
  7  8  2  0
 16  8  1  0
  9 15  1  0
  6  9  2  0
 10  5  1  0
 11 10  2  0
 12 11  1  0
  3 12  1  0
 13 12  2  0
 14 13  1  0
  1 14  2  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 24 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884995

   ---

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: 375.49

Molecular Weight (Monoisotopic): 375.1293

AlogP: 5.53

#Rotatable Bonds: 6

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: 4.24

CX Basic pKa: 9.76

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -0.65

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