2-(3,4-Dichlorophenyl)-N-((6-(4-(trifluoromethyl)phenyl)imidazo[2,1-b]thiazol-5-yl)methyl)ethan-1-amine

ID: ALA4574886

PubChem CID: 142505424

Max Phase: Preclinical

Molecular Formula: C21H16Cl2F3N3S

Molecular Weight: 470.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  FC(F)(F)c1ccc(-c2nc3sccn3c2CNCCc2ccc(Cl)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C21H16Cl2F3N3S/c22-16-6-1-13(11-17(16)23)7-8-27-12-18-19(28-20-29(18)9-10-30-20)14-2-4-15(5-3-14)21(24,25)26/h1-6,9-11,27H,7-8,12H2

Standard InChI Key:  YFQXADHNTBCBFF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   21.2797  -12.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2432  -11.5317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7840  -12.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0294  -11.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0498  -12.5811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8331  -12.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2969  -12.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8001  -11.4922    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9700  -12.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0475  -13.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6099  -14.2311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3776  -15.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9400  -15.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7078  -16.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9125  -16.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6801  -17.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2428  -17.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0410  -17.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2696  -16.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0116  -18.7364    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8854  -17.5490    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.5468  -11.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7337  -11.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3470  -12.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7795  -12.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5912  -12.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5302  -12.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7869  -12.3287    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.9701  -11.6607    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.0115  -12.9840    0.0000 F   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
  3  9  1  0
  1 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 16 21  1  0
  9 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  9  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4574886

   ---

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: 470.35

Molecular Weight (Monoisotopic): 469.0394

AlogP: 6.72

#Rotatable Bonds: 6

Polar Surface Area: 29.33

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.43

CX LogP: 6.40

CX LogD: 4.39

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.32

Np Likeness Score: -1.83

References

1. Liang D, Li L, Lynch C, Mackowiak B, Hedrich WD, Ai Y, Yin Y, Heyward S, Xia M, Wang H, Xue F..  (2019)  Human constitutive androstane receptor agonist DL5016: A novel sensitizer for cyclophosphamide-based chemotherapies.,  179  [PMID:31247375] [10.1016/j.ejmech.2019.06.031]

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