6-(Hydroxymethyl)-2-(4-(piperidin-1-ylmethyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

ID: ALA4069874

PubChem CID: 137639205

Max Phase: Preclinical

Molecular Formula: C23H29N3O3S

Molecular Weight: 427.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=O)c2ccc(CN3CCCCC3)cc2)sc2c1CCC(CO)C2

Standard InChI:  InChI=1S/C23H29N3O3S/c24-21(28)20-18-9-6-16(14-27)12-19(18)30-23(20)25-22(29)17-7-4-15(5-8-17)13-26-10-2-1-3-11-26/h4-5,7-8,16,27H,1-3,6,9-14H2,(H2,24,28)(H,25,29)

Standard InChI Key:  XNXQXKGYYKFAPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.3599   -3.9292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.6142   -3.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9513   -2.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9500   -1.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6571   -1.4435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2417   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3918   -2.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9983   -3.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7759   -3.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8273   -4.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3783   -3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1552   -3.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3268   -2.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7154   -2.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9408   -2.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5427   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2910   -3.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5007   -2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9564   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2080   -4.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0040   -4.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1041   -2.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7113   -2.9905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5371   -3.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1404   -4.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9192   -4.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0913   -3.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4845   -2.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6611   -4.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8618   -4.8011    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 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 20 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069874

   ---

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: 427.57

Molecular Weight (Monoisotopic): 427.1930

AlogP: 3.18

#Rotatable Bonds: 6

Polar Surface Area: 95.66

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.81

CX LogP: 3.82

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.49

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