N-(3-(pyridin-2-ylmethylcarbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide

ID: ALA5285158

Max Phase: Preclinical

Molecular Formula: C21H20N4O2S

Molecular Weight: 392.48

Names and Identifiers

Canonical SMILES:  O=C(Nc1sc2c(c1C(=O)NCc1ccccn1)CCCC2)c1cccnc1

Standard InChI:  InChI=1S/C21H20N4O2S/c26-19(14-6-5-10-22-12-14)25-21-18(16-8-1-2-9-17(16)28-21)20(27)24-13-15-7-3-4-11-23-15/h3-7,10-12H,1-2,8-9,13H2,(H,24,27)(H,25,26)

Standard InChI Key:  GQQVLRFJWVPNLD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.2769    0.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -0.8310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -1.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622   -0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -2.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1329   -0.8347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5816   -1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5816   -2.0726    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3858   -2.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8566   -1.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782   -0.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752    0.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946    0.3791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    1.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6247    1.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    2.5570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557    3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    2.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556    2.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    1.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -3.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5181   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582   -1.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 11 10  1  0
 11 12  1  0
 12 13  2  0
 14 13  1  0
 10 14  2  0
 14 15  1  0
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 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 12 25  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 13 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285158

   ---

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: 392.48

Molecular Weight (Monoisotopic): 392.1307

AlogP: 3.60

#Rotatable Bonds: 5

Polar Surface Area: 83.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.23

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -2.36

References

1. Wang KM, Ge YX, Zhang J, Chen YT, Zhang NY, Gu JS, Fang L, Zhang XL, Zhang J, Jiang CS..  (2023)  New cycloalkyl[b]thiophenylnicotinamide-based α-glucosidase inhibitors as promising anti-diabetic agents: Synthesis, in silico study, in vitro and in vivo evaluations.,  79  [PMID:36395995] [10.1016/j.bmcl.2022.129069]

Source

Source(1):

• Scientific Literature