2-(4-((1,1-Dioxidothiomorpholino)methyl)benzamido)-6-(hydroxymethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

ID: ALA4062022

PubChem CID: 137637550

Max Phase: Preclinical

Molecular Formula: C22H27N3O5S2

Molecular Weight: 477.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=O)c2ccc(CN3CCS(=O)(=O)CC3)cc2)sc2c1CCC(CO)C2

Standard InChI:  InChI=1S/C22H27N3O5S2/c23-20(27)19-17-6-3-15(13-26)11-18(17)31-22(19)24-21(28)16-4-1-14(2-5-16)12-25-7-9-32(29,30)10-8-25/h1-2,4-5,15,26H,3,6-13H2,(H2,23,27)(H,24,28)

Standard InChI Key:  GBEPILPAVQVXJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   37.5248  -14.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7365  -14.7260    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.9483  -15.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1783  -14.5733    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.4326  -13.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7697  -13.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7684  -12.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4755  -12.0876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0601  -12.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2102  -13.5451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8167  -14.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5943  -13.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6457  -14.8919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1967  -14.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9736  -14.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1452  -13.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5338  -12.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7592  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3611  -14.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1094  -13.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3191  -13.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7748  -14.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0264  -15.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8224  -15.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9225  -13.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5297  -13.6347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3555  -14.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9588  -14.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9097  -13.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3029  -13.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4795  -15.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6802  -15.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 19  4  1  0
  4  5  1  0
  5  6  2  0
  6 20  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 19 20  2  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
 26 27  1  0
 26 30  1  0
 27 28  1  0
 28  2  1  0
  2 29  1  0
 29 30  1  0
 23 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062022

   ---

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: 477.61

Molecular Weight (Monoisotopic): 477.1392

AlogP: 1.43

#Rotatable Bonds: 6

Polar Surface Area: 129.80

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.87

CX LogP: 1.63

CX LogD: 1.63

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -1.67

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