1-(5-((6-(thiazolo[5,4-b]pyridin-2-yloxy)benzofuran-3-yl)methyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethanone

ID: ALA2313557

PubChem CID: 59577731

Max Phase: Preclinical

Molecular Formula: C22H20N4O3S

Molecular Weight: 420.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CC2CC1CN2Cc1coc2cc(Oc3nc4cccnc4s3)ccc12

Standard InChI:  InChI=1S/C22H20N4O3S/c1-13(27)26-11-15-7-16(26)10-25(15)9-14-12-28-20-8-17(4-5-18(14)20)29-22-24-19-3-2-6-23-21(19)30-22/h2-6,8,12,15-16H,7,9-11H2,1H3

Standard InChI Key:  MCQDKCRFPCIJBM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 35  0  0  0  0  0  0  0  0999 V2000
   26.0413  -24.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5907  -24.0055    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.3398  -23.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2703  -22.8727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4751  -22.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0539  -23.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0794  -21.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2623  -21.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8410  -22.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2368  -23.3746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4511  -22.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7462  -22.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7462  -23.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4512  -24.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9352  -22.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1602  -22.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1605  -23.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9370  -23.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4140  -23.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3149  -21.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1315  -21.8716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5625  -22.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3755  -22.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7591  -21.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3234  -21.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5042  -21.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5758  -21.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0100  -22.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9582  -21.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2060  -21.5524    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
 24 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  1  0
 30 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2313557

   1-[5-[[6-([1,3]Thiazolo[5,4-b]pyridin-2-yloxy)-1-benzofuran-3-yl]methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]ethanone

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: 420.49

Molecular Weight (Monoisotopic): 420.1256

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 71.70

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.25

CX LogP: 2.63

CX LogD: 2.40

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.93

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