5-chloro-N-(2,4-dimethoxybenzyl)-3-methoxybenzo[b]thiophene-2-carboxamide

ID: ALA5290395

Max Phase: Preclinical

Molecular Formula: C19H18ClNO4S

Molecular Weight: 391.88

Names and Identifiers

Canonical SMILES:  COc1ccc(CNC(=O)c2sc3ccc(Cl)cc3c2OC)c(OC)c1

Standard InChI:  InChI=1S/C19H18ClNO4S/c1-23-13-6-4-11(15(9-13)24-2)10-21-19(22)18-17(25-3)14-8-12(20)5-7-16(14)26-18/h4-9H,10H2,1-3H3,(H,21,22)

Standard InChI Key:  TVGFCIHBTSPJTF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -3.2444   -0.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456   -1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329   -2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5347   -0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8165   -1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0269   -2.0509    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347   -0.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    0.0735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184    0.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9569   -0.5634    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -0.6580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5085   -0.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368    0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    0.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    1.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014    1.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756    0.7596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571    1.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1343    2.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  1  1  0
  5  4  2  0
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  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
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  1 12  1  0
  8 13  1  0
 13 14  2  0
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 15 16  1  0
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 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 23 24  1  0
 20 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290395

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.88

Molecular Weight (Monoisotopic): 391.0645

AlogP: 4.51

#Rotatable Bonds: 6

Polar Surface Area: 56.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -1.34

References

1. Spanò V, Venturini A, Genovese M, Barreca M, Raimondi MV, Montalbano A, Galietta LJV, Barraja P..  (2020)  Current development of CFTR potentiators in the last decade.,  204  [PMID:32898816] [10.1016/j.ejmech.2020.112631]

Source

Source(1):

• Scientific Literature