2-(5-Ethyl-4-hydroxy-6-methyl-pyrimidin-2-ylsulfanyl)-N-[5-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide

ID: ALA4781948

PubChem CID: 139024910

Max Phase: Preclinical

Molecular Formula: C19H20N4O3S2

Molecular Weight: 416.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1c(C)nc(SCC(=O)Nc2ncc(-c3ccc(OC)cc3)s2)nc1O

Standard InChI:  InChI=1S/C19H20N4O3S2/c1-4-14-11(2)21-19(23-17(14)25)27-10-16(24)22-18-20-9-15(28-18)12-5-7-13(26-3)8-6-12/h5-9H,4,10H2,1-3H3,(H,20,22,24)(H,21,23,25)

Standard InChI Key:  VJTRWLBHMXKGFT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   19.1920   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4801   -4.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4801   -3.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6954   -3.6077    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.2104   -4.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6954   -4.9425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3853   -4.2752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9728   -3.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1479   -3.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3853   -2.8462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9087   -3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6203   -3.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6159   -2.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8939   -2.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1854   -2.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3273   -2.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0449   -2.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7353   -4.2752    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9103   -4.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5028   -3.5613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6785   -3.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2652   -4.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6821   -4.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5050   -4.9897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721   -5.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4401   -4.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0267   -3.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2664   -2.8462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  2  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  1 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  1  1  0
 13 16  1  0
 16 17  1  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781948

   ---

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: 416.53

Molecular Weight (Monoisotopic): 416.0977

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 97.23

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.89

CX Basic pKa: 1.49

CX LogP: 4.17

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.99

References

1. Choi SH,Ryu S,Sim K,Song C,Shin I,Kim SS,Lee YS,Park JY,Sim T.  (2020)  Anti-glioma effects of 2-aminothiophene-3-carboxamide derivatives, ANO1 channel blockers.,  208  [PMID:32906067] [10.1016/j.ejmech.2020.112688]

2. Tradtrantip, Lukmanee L, Namkung, Wan W and Verkman, A S AS.  2010-01  Crofelemer, an antisecretory antidiarrheal proanthocyanidin oligomer extracted from Croton lechleri, targets two distinct intestinal chloride channels.  [PMID:19808995]

3. Kumar, Satish; Namkung, Wan; Verkman, A S and Sharma, Pawan K.  2012-07-15  Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors.  [PMID:22739085]

4. Truong, Eric C EC and 11 more authors.  2017-06-08  Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A).  [PMID:28493701]

5. Seo, Yohan Y and 5 more authors.  2018-12-05  Synthesis and biological evaluation of novel Ani9 derivatives as potent and selective ANO1 inhibitors.  [PMID:30347323]

6. Choi, Seung-Hye and 8 more authors.  2020-12-15  Anti-glioma effects of 2-aminothiophene-3-carboxamide derivatives, ANO1 channel blockers.  [PMID:32906067]

Source

Source(1):

• Scientific Literature