4-(((5-(naphthalen-2-yl)benzo[b]thiophen-2-yl)methylamino)methyl)benzoic acid

ID: ALA3884941

PubChem CID: 134130243

Max Phase: Preclinical

Molecular Formula: C27H21NO2S

Molecular Weight: 423.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CNCc2cc3cc(-c4ccc5ccccc5c4)ccc3s2)cc1

Standard InChI:  InChI=1S/C27H21NO2S/c29-27(30)20-7-5-18(6-8-20)16-28-17-25-15-24-14-23(11-12-26(24)31-25)22-10-9-19-3-1-2-4-21(19)13-22/h1-15,28H,16-17H2,(H,29,30)

Standard InChI Key:  LZCNYSKXQPCDBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   13.2724   -6.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8273   -7.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2072   -8.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0322   -8.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4760   -7.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0936   -6.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4137   -9.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9710   -9.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5050   -4.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2258   -5.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9371   -4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499   -5.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3639   -4.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -5.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0853   -5.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7999   -6.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7922   -4.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570   -3.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6348   -3.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236   -3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -3.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -3.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078   -5.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5152   -5.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3044   -6.2054    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7847   -5.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2922   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096   -5.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0285   -6.2348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8535   -6.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2379   -9.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 13 14  1  0
 15 14  1  0
 15 16  2  0
 24 16  1  0
 17 23  1  0
 14 17  2  0
 18 13  1  0
 19 18  2  0
 20 19  1  0
 11 20  1  0
 21 20  2  0
 22 21  1  0
  9 22  2  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30  1  1  0
  7 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884941

   ---

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: 423.54

Molecular Weight (Monoisotopic): 423.1293

AlogP: 6.71

#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: 3.81

CX Basic pKa: 8.68

CX LogP: 4.09

CX LogD: 4.07

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: -0.88

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