1-((6-(thiazolo[4,5-b]pyridin-2-yloxy)benzofuran-3-yl)methyl)piperidine-4-carboxylic acid

ID: ALA2313567

PubChem CID: 59577737

Max Phase: Preclinical

Molecular Formula: C21H19N3O4S

Molecular Weight: 409.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1CCN(Cc2coc3cc(Oc4nc5ncccc5s4)ccc23)CC1

Standard InChI:  InChI=1S/C21H19N3O4S/c25-20(26)13-5-8-24(9-6-13)11-14-12-27-17-10-15(3-4-16(14)17)28-21-23-19-18(29-21)2-1-7-22-19/h1-4,7,10,12-13H,5-6,8-9,11H2,(H,25,26)

Standard InChI Key:  QLODKRVWQXTRHR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   16.9903  -10.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5356  -10.7282    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2888  -10.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2193   -9.5871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4200   -9.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9946  -10.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0201   -8.6816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1989   -8.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7776   -9.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1734  -10.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4084   -9.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6993   -9.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6993  -10.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4084  -10.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9007   -9.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1216   -9.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1219  -10.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9025  -10.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3836  -10.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2846   -8.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1052   -8.5819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5362   -9.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3534   -9.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7411   -8.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3013   -7.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4779   -7.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5619   -8.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9961   -9.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9443   -7.7635    0.0000 O   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
 24 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2313567

   1-[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidine-4-carboxylic acid

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: 409.47

Molecular Weight (Monoisotopic): 409.1096

AlogP: 4.53

#Rotatable Bonds: 5

Polar Surface Area: 88.69

Molecular Species: ZWITTERION

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.14

CX Basic pKa: 8.88

CX LogP: 0.85

CX LogD: 0.84

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -1.04

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