6-amino-N-(1-(2,5-dichloropyridin-4-yl)azetidin-3-yl)-2,5-dimethylthieno[3,2-e][1,2,4]triazolo[1,5-a]pyridine-7-carboxamide

ID: ALA4534301

PubChem CID: 134207682

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N7OS

Molecular Weight: 462.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc2cc(C)c3c(N)c(C(=O)NC4CN(c5cc(Cl)ncc5Cl)C4)sc3n2n1

Standard InChI:  InChI=1S/C19H17Cl2N7OS/c1-8-3-14-24-9(2)26-28(14)19-15(8)16(22)17(30-19)18(29)25-10-6-27(7-10)12-4-13(21)23-5-11(12)20/h3-5,10H,6-7,22H2,1-2H3,(H,25,29)

Standard InChI Key:  WGXRXURVGSDLOI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   12.7862  -14.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4914  -14.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1967  -14.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2012  -15.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9764  -15.4979    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.4511  -14.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9692  -14.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4914  -15.6587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7840  -15.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1844  -15.8072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5213  -16.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3290  -16.4553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4914  -13.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2174  -13.4029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2683  -14.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6808  -15.5379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6730  -14.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4980  -15.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1187  -17.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0748  -16.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6495  -15.5270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0684  -14.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4666  -15.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8750  -16.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6914  -16.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0969  -15.5169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6800  -14.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8650  -14.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0822  -14.0978    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.4679  -16.9401    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  1  2  2  0
  8  4  1  0
  3  2  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  2 13  1  0
  7 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 11 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534301

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 462.37

Molecular Weight (Monoisotopic): 461.0592

AlogP: 3.46

#Rotatable Bonds: 3

Polar Surface Area: 101.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.05

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -1.92

References

1. Chopko TC, Han C, Gregro AR, Engers DW, Felts AS, Poslusney MS, Bollinger KA, Morrison RD, Bubser M, Lamsal A, Luscombe VB, Cho HP, Schnetz-Boutaud NC, Rodriguez AL, Chang S, Daniels JS, Stec DF, Niswender CM, Jones CK, Wood MR, Wood MW, Duggan ME, Brandon NJ, Conn PJ, Bridges TM, Lindsley CW, Melancon BJ..  (2019)  SAR inspired by aldehyde oxidase (AO) metabolism: Discovery of novel, CNS penetrant tricyclic M4 PAMs.,  29  (16): [PMID:31248774] [10.1016/j.bmcl.2019.06.032]

Source

Source(1):

• Scientific Literature