N-(3-(4-hydroxy-3-methoxybenzylcarbamoyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)nicotinamide

ID: ALA5283691

Max Phase: Preclinical

Molecular Formula: C22H21N3O4S

Molecular Weight: 423.49

Names and Identifiers

Canonical SMILES:  COc1cc(CNC(=O)c2c(NC(=O)c3cccnc3)sc3c2CCC3)ccc1O

Standard InChI:  InChI=1S/C22H21N3O4S/c1-29-17-10-13(7-8-16(17)26)11-24-21(28)19-15-5-2-6-18(15)30-22(19)25-20(27)14-4-3-9-23-12-14/h3-4,7-10,12,26H,2,5-6,11H2,1H3,(H,24,28)(H,25,27)

Standard InChI Key:  JHOZJHIYUZQILN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
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    2.0954   -0.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073   -1.4156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808   -1.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662   -1.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662   -2.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -1.4193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -1.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -2.6570    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672   -2.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379   -2.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5459   -1.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -0.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    0.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061    1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194    1.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371    2.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0056    0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073   -3.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7984   -2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    2.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507    3.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4478    3.5642    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
 15 16  2  0
 15 17  1  0
 17 18  1  0
 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
 25 26  1  0
 27 26  1  0
 13 27  1  0
 22 28  1  0
 21 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283691

   ---

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: 423.49

Molecular Weight (Monoisotopic): 423.1253

AlogP: 3.53

#Rotatable Bonds: 6

Polar Surface Area: 100.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.93

CX Basic pKa: 3.50

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -1.57

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