N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-phenylacetamide

ID: ALA397167

Cas Number: 301307-93-7

PubChem CID: 684674

Max Phase: Preclinical

Molecular Formula: C17H16N2OS

Molecular Weight: 296.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(NC(=O)Cc2ccccc2)sc2c1CCCC2

Standard InChI:  InChI=1S/C17H16N2OS/c18-11-14-13-8-4-5-9-15(13)21-17(14)19-16(20)10-12-6-2-1-3-7-12/h1-3,6-7H,4-5,8-10H2,(H,19,20)

Standard InChI Key:  XAECXGNGYGUEJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -5.9063  -10.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063  -11.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921  -11.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921   -9.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867  -11.3333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2029  -10.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6891   -9.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4732  -10.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718  -11.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781  -10.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334   -9.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800   -8.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9644  -11.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755  -12.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396  -11.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7259  -12.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1414  -12.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7285  -13.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972  -13.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082  -12.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928  -12.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 10  1  0
  8  9  2  0
 11 12  3  0
  7 11  1  0
  1  2  1  0
 10 13  1  0
  6  7  2  0
 13 14  2  0
  1  4  1  0
 13 15  1  0
  2  3  1  0
 15 16  1  0
  3  9  1  0
 16 17  2  0
  5  6  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  8  4  1  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA397167

   N-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-2-phenylacetamide

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: 296.39

Molecular Weight (Monoisotopic): 296.0983

AlogP: 3.68

#Rotatable Bonds: 3

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.42

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.94

Np Likeness Score: -2.28

References

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2. Nankervis JL, Feil SC, Hancock NC, Zheng Z, Ng HL, Morton CJ, Holien JK, Ho PW, Frazzetto MM, Jennings IG, Manallack DT, Martin TJ, Thompson PE, Parker MW..  (2011)  Thiophene inhibitors of PDE4: crystal structures show a second binding mode at the catalytic domain of PDE4D2.,  21  (23): [PMID:22030030] [10.1016/j.bmcl.2011.09.109]

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15. He, Yuanjun and 9 more authors.  2014-01-01  Synthesis and SAR of novel isoxazoles as potent c-jun N-terminal kinase (JNK) inhibitors.  [PMID:24332487]

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Source

Source(1):

• Scientific Literature