2-(4-(Morpholinomethyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

ID: ALA4096148

PubChem CID: 137655267

Max Phase: Preclinical

Molecular Formula: C21H25N3O3S

Molecular Weight: 399.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=O)c2ccc(CN3CCOCC3)cc2)sc2c1CCCC2

Standard InChI:  InChI=1S/C21H25N3O3S/c22-19(25)18-16-3-1-2-4-17(16)28-21(18)23-20(26)15-7-5-14(6-8-15)13-24-9-11-27-12-10-24/h5-8H,1-4,9-13H2,(H2,22,25)(H,23,26)

Standard InChI Key:  XNGFBSQNUPKFGT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.1602  -16.9217    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4146  -16.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516  -15.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504  -14.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575  -14.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420  -14.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921  -15.8935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7987  -16.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5762  -16.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6276  -17.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786  -16.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9556  -16.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1272  -15.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5158  -15.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7412  -15.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430  -16.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0914  -16.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011  -15.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567  -16.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0084  -17.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8043  -17.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9044  -15.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5117  -15.9831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3374  -16.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9407  -17.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7196  -17.0771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8917  -16.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2849  -15.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  0
  1  2  1  0
  2  3  2  0
  3 17  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096148

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 399.52

Molecular Weight (Monoisotopic): 399.1617

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 84.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.60

CX LogP: 3.82

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: -2.13

References

1. Llona-Minguez S, Fayezi S, Alihemmati A, Juárez-Jiménez J, Piedrafita FJ, Helleday T..  (2017)  Tetrahydrobenzothiophene carboxamides: Beyond the kinase domain and into the fatty acid realm.,  27  (18): [PMID:28807439] [10.1016/j.bmcl.2017.08.006]

Source

Source(1):

• Scientific Literature