2-(3-(piperidin-1-ylmethyl)benzofuran-6-yloxy)benzo[d]thiazole

ID: ALA2313560

PubChem CID: 49834447

Max Phase: Preclinical

Molecular Formula: C21H20N2O2S

Molecular Weight: 364.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc2sc(Oc3ccc4c(CN5CCCCC5)coc4c3)nc2c1

Standard InChI:  InChI=1S/C21H20N2O2S/c1-4-10-23(11-5-1)13-15-14-24-19-12-16(8-9-17(15)19)25-21-22-18-6-2-3-7-20(18)26-21/h2-3,6-9,12,14H,1,4-5,10-11,13H2

Standard InChI Key:  XAILZKMAGMYSMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   26.2107  -11.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7463  -11.1223    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5025  -10.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4324   -9.9786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6296   -9.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2043  -10.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2300   -9.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4052   -9.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9799   -9.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3794  -10.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6340   -9.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9223   -9.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9223  -10.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6340  -11.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1322   -9.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3498   -9.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3501  -10.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1340  -11.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6156  -10.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5156   -9.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3398   -8.9680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7751   -9.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5958   -9.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9831   -8.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5432   -8.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7162   -8.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  2  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  6 10  2  0
  5  7  2  0
  1  3  1  0
 16 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 17 14  2  0
 16 17  1  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
 13  1  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2313560

   2-[[3-(Piperidin-1-ylmethyl)-1-benzofuran-6-yl]oxy]-1,3-benzothiazole

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: 364.47

Molecular Weight (Monoisotopic): 364.1245

AlogP: 5.82

#Rotatable Bonds: 4

Polar Surface Area: 38.50

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 5.25

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: -1.35

References

1. Eccles W, Blevitt JM, Booker JN, Chrovian CC, Crawford S, de Leon AR, Deng X, Fourie AM, Grice CA, Herman K, Karlsson L, Kearney AM, Lee-Dutra A, Liang J, Luna R, Pippel D, Rao N, Riley JP, Santillán A, Savall B, Tanis VM, Xue X, Young AL..  (2013)  Identification of benzofuran central cores for the inhibition of leukotriene A(4) hydrolase.,  23  (3): [PMID:23260350] [10.1016/j.bmcl.2012.11.074]

Source

Source(1):

• Scientific Literature