3-Carbamoyl-2-(4-(morpholinomethyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carboxylic acid, ammonia salt

ID: ALA4080558

PubChem CID: 137648291

Max Phase: Preclinical

Molecular Formula: C22H28N4O5S

Molecular Weight: 443.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N.NC(=O)c1c(NC(=O)c2ccc(CN3CCOCC3)cc2)sc2c1CCC(C(=O)O)C2

Standard InChI:  InChI=1S/C22H25N3O5S.H3N/c23-19(26)18-16-6-5-15(22(28)29)11-17(16)31-21(18)24-20(27)14-3-1-13(2-4-14)12-25-7-9-30-10-8-25;/h1-4,15H,5-12H2,(H2,23,26)(H,24,27)(H,28,29);1H3

Standard InChI Key:  HIXXIVUOGDTWJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   12.3161  -15.9696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9305  -15.1179    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.1874  -14.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5180  -13.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5168  -13.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2306  -12.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8015  -12.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9724  -14.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5847  -14.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3698  -14.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4121  -15.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9780  -14.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7625  -14.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9358  -13.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3184  -13.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5364  -13.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1054  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8514  -14.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0534  -14.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5039  -14.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7579  -15.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5615  -15.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7204  -13.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3335  -14.1703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1576  -14.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7667  -15.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5531  -15.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7268  -14.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1142  -13.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2057  -16.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3987  -15.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4605  -16.9547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17  2  1  0
  2  3  1  0
  3  4  2  0
  4 18  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 10  1  0
 17 18  2  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 21 30  1  0
 30 31  1  0
 30 32  2  0
M  END

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: 443.53

Molecular Weight (Monoisotopic): 443.1515

AlogP: 2.12

#Rotatable Bonds: 6

Polar Surface Area: 121.96

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: 6.60

CX LogP: 0.46

CX LogD: -0.16

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -1.62

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