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

ID: ALA4063392

PubChem CID: 137637115

Max Phase: Preclinical

Molecular Formula: C20H25N3O3S

Molecular Weight: 387.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc(C(=O)Nc2sc3c(c2C(N)=O)CCC(CO)C3)cc1

Standard InChI:  InChI=1S/C20H25N3O3S/c1-23(2)10-12-3-6-14(7-4-12)19(26)22-20-17(18(21)25)15-8-5-13(11-24)9-16(15)27-20/h3-4,6-7,13,24H,5,8-11H2,1-2H3,(H2,21,25)(H,22,26)

Standard InChI Key:  HUBSGXCDUQSQLS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   30.4383   -9.1171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.6926   -8.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0297   -7.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0284   -7.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7355   -6.6314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3201   -6.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4702   -8.0889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0767   -8.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8543   -8.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9057   -9.4357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4567   -8.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2336   -8.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4053   -7.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7938   -7.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0193   -7.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6211   -9.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3694   -8.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5791   -8.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0348   -8.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2864   -9.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0824   -9.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1825   -7.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7897   -8.1785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6155   -8.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5629   -7.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7395  -10.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9402   -9.9890    0.0000 O   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 25  1  0
 20 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063392

   ---

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: 387.51

Molecular Weight (Monoisotopic): 387.1617

AlogP: 2.26

#Rotatable Bonds: 6

Polar Surface Area: 95.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.48

CX LogP: 2.97

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -1.52

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