4-(3-cyano-6-ethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxobut-2-enoic acid

ID: ALA4795619

PubChem CID: 6013831

Max Phase: Preclinical

Molecular Formula: C15H16N2O3S

Molecular Weight: 304.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC1CCc2c(sc(NC(=O)/C=C/C(=O)O)c2C#N)C1

Standard InChI:  InChI=1S/C15H16N2O3S/c1-2-9-3-4-10-11(8-16)15(21-12(10)7-9)17-13(18)5-6-14(19)20/h5-6,9H,2-4,7H2,1H3,(H,17,18)(H,19,20)/b6-5+

Standard InChI Key:  KBEMPPDUIDFFHB-AATRIKPKSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    1.7995  -11.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995  -12.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048  -13.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048  -11.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100  -11.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145  -12.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941  -13.0027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714  -12.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868  -11.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359  -10.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841  -10.1178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924  -13.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841  -12.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886  -12.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -13.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5183  -13.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965  -13.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9308  -13.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7480  -13.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1634  -14.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1555  -13.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  3  0
  9 10  1  0
  2 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795619

   (2E)-4-[(3-cyano-6-ethyl-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)amino]-4-oxobut-2-enoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 304.37

Molecular Weight (Monoisotopic): 304.0882

AlogP: 2.71

#Rotatable Bonds: 4

Polar Surface Area: 90.19

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.26

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: -0.01

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -1.34

References

1. Hou X,Sun JP,Ge L,Liang X,Li K,Zhang Y,Fang H.  (2020)  Inhibition of striatal-enriched protein tyrosine phosphatase by targeting computationally revealed cryptic pockets.,  190  [PMID:32078861] [10.1016/j.ejmech.2020.112131]

Source

Source(1):

• Scientific Literature