(E)-4-(5-((((3,4-Dichlorobenzyl)oxy)imino)methyl)imidazo[2,1-b]thiazol-6-yl)benzonitrile

ID: ALA4582135

PubChem CID: 142505438

Max Phase: Preclinical

Molecular Formula: C20H12Cl2N4OS

Molecular Weight: 427.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2nc3sccn3c2/C=N/OCc2ccc(Cl)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C20H12Cl2N4OS/c21-16-6-3-14(9-17(16)22)12-27-24-11-18-19(25-20-26(18)7-8-28-20)15-4-1-13(10-23)2-5-15/h1-9,11H,12H2/b24-11+

Standard InChI Key:  HAOPXYFUPPKWEG-BHGWPJFGSA-N

Molfile:  

 
     RDKit          2D

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   42.9075  -13.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8918  -12.2937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4194  -12.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6720  -12.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6771  -13.3538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4555  -13.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9315  -12.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4472  -12.2799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.6651  -14.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8680  -14.5766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6255  -15.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8285  -15.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5860  -16.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7901  -16.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5476  -17.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1025  -17.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9031  -17.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1419  -16.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8611  -18.6573    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   38.7504  -17.4553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   41.6046  -12.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1883  -12.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3719  -12.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9709  -12.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3923  -13.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2073  -13.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1570  -13.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3399  -13.0153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  2  0
  2  3  1  0
  3  1  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  1  9  1  0
  9 10  2  0
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 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
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 16 19  1  0
 15 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  3 21  1  0
 27 28  3  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582135

   ---

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: 427.32

Molecular Weight (Monoisotopic): 426.0109

AlogP: 5.79

#Rotatable Bonds: 5

Polar Surface Area: 62.68

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.60

CX LogP: 5.63

CX LogD: 5.63

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -2.08

References

1. Liang D, Li L, Lynch C, Diethelm-Varela B, Xia M, Xue F, Wang H..  (2019)  DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor.,  10  (7): [PMID:31312405] [10.1021/acsmedchemlett.9b00079]

2. Forman, B M BM and 7 more authors.  1998-10-08  Androstane metabolites bind to and deactivate the nuclear receptor CAR-beta.  [PMID:9783588]

3. Maglich, Jodi M JM and 10 more authors.  2003-05-09  Identification of a novel human constitutive androstane receptor (CAR) agonist and its use in the identification of CAR target genes.  [PMID:12611900]

4. Huang, Wendong W, Zhang, Jun J, Wei, Ping P, Schrader, William T WT and Moore, David D DD.  2004-10  Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR.  [PMID:15272053]

5. Gege, Christian C, Schlüter, Thomas T and Hoffmann, Thomas T.  2014-11-15  Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt.  [PMID:25305688]

6. Pellicciari, Roberto R and 12 more authors.  2016-10-13  Discovery of 3α,7α,11β-Trihydroxy-6α-ethyl-5β-cholan-24-oic Acid (TC-100), a Novel Bile Acid as Potent and Highly Selective FXR Agonist for Enterohepatic Disorders.  [PMID:27652492]

Source

Source(1):

• Scientific Literature