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

ID: ALA4088423

PubChem CID: 137642084

Max Phase: Preclinical

Molecular Formula: C22H27N3O4S

Molecular Weight: 429.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=O)c2ccc(CN3CCOCC3)cc2)sc2c1CCC(CO)C2

Standard InChI:  InChI=1S/C22H27N3O4S/c23-20(27)19-17-6-3-15(13-26)11-18(17)30-22(19)24-21(28)16-4-1-14(2-5-16)12-25-7-9-29-10-8-25/h1-2,4-5,15,26H,3,6-13H2,(H2,23,27)(H,24,28)

Standard InChI Key:  LVAXPNLWVSQKIP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   17.0826   -3.7104    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3369   -2.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6740   -2.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6727   -1.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3798   -1.2247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9644   -1.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1145   -2.6823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7210   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4986   -2.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5500   -4.0290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1010   -3.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8779   -3.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0495   -2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4381   -1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6635   -2.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2654   -3.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0137   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2234   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6791   -3.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9307   -4.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7267   -4.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8268   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4340   -2.7718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2598   -3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631   -4.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6419   -3.8658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8140   -3.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2072   -2.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3838   -4.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5845   -4.5823    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:

   

   ALA4088423

   ---

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: 429.54

Molecular Weight (Monoisotopic): 429.1722

AlogP: 2.03

#Rotatable Bonds: 6

Polar Surface Area: 104.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.60

CX LogP: 2.75

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.65

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