2-(3-Benzoylthioureido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide

ID: ALA4757077

PubChem CID: 4504215

Max Phase: Preclinical

Molecular Formula: C16H15N3O2S2

Molecular Weight: 345.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=S)NC(=O)c2ccccc2)sc2c1CCC2

Standard InChI:  InChI=1S/C16H15N3O2S2/c17-13(20)12-10-7-4-8-11(10)23-15(12)19-16(22)18-14(21)9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H2,17,20)(H2,18,19,21,22)

Standard InChI Key:  IRRJZAVFRDACKO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.8429  -24.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -24.8247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307  -25.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307  -24.1535    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767  -26.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699  -26.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6294  -26.8856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1196  -25.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9116  -25.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3968  -24.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9045  -24.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1211  -24.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054  -24.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7804  -24.1103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -23.3958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679  -24.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429  -24.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7804  -25.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1355  -24.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113  -24.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8979  -24.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3148  -25.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1377  -25.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3  8  1  0
 12  4  1  0
  4  1  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 12  2  0
  2 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757077

   2-(benzoylcarbamothioylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide

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: 345.45

Molecular Weight (Monoisotopic): 345.0606

AlogP: 2.46

#Rotatable Bonds: 3

Polar Surface Area: 84.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.64

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -2.38

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