Ethyl 3-carbamoyl-2-(4-(morpholinomethyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carboxylate

ID: ALA4067164

PubChem CID: 137631365

Max Phase: Preclinical

Molecular Formula: C24H29N3O5S

Molecular Weight: 471.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1CCc2c(sc(NC(=O)c3ccc(CN4CCOCC4)cc3)c2C(N)=O)C1

Standard InChI:  InChI=1S/C24H29N3O5S/c1-2-32-24(30)17-7-8-18-19(13-17)33-23(20(18)21(25)28)26-22(29)16-5-3-15(4-6-16)14-27-9-11-31-12-10-27/h3-6,17H,2,7-14H2,1H3,(H2,25,28)(H,26,29)

Standard InChI Key:  HMWWISUHIQOXJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    4.4078  -22.8566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6622  -22.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993  -21.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980  -20.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051  -20.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897  -20.3731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398  -21.8285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463  -22.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238  -22.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753  -23.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4263  -22.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2032  -22.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3748  -21.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7634  -21.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9888  -21.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5907  -22.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390  -22.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487  -21.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044  -22.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560  -23.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520  -23.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1520  -21.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7593  -21.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5851  -22.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1884  -23.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9672  -23.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1393  -22.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5325  -21.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091  -23.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098  -23.7286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614  -24.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3628  -24.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365  -24.1656    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
 20 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067164

   ---

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: 471.58

Molecular Weight (Monoisotopic): 471.1828

AlogP: 2.60

#Rotatable Bonds: 7

Polar Surface Area: 110.96

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.86

CX Basic pKa: 6.60

CX LogP: 3.55

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: -1.61

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