8-(Methylthio)-N-(2-(thiazol-2-yl)ethyl)quinoline-3-carboxamide

ID: ALA4070030

PubChem CID: 126609831

Max Phase: Preclinical

Molecular Formula: C16H15N3OS2

Molecular Weight: 329.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1cccc2cc(C(=O)NCCc3nccs3)cnc12

Standard InChI:  InChI=1S/C16H15N3OS2/c1-21-13-4-2-3-11-9-12(10-19-15(11)13)16(20)18-6-5-14-17-7-8-22-14/h2-4,7-10H,5-6H2,1H3,(H,18,20)

Standard InChI Key:  CXOUBSQVKSFXEB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   25.9862   -9.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9851  -10.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6999  -10.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6981   -8.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4134   -9.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4142  -10.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1295  -10.4592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8446  -10.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8398   -9.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1240   -8.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7018  -11.2902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.5518   -8.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2688   -9.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5467   -7.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9807   -8.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6976   -9.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4096   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1628   -9.1139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7111   -8.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2942   -7.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4883   -7.9620    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.9882  -11.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 11 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4070030

   ---

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: 329.45

Molecular Weight (Monoisotopic): 329.0657

AlogP: 3.39

#Rotatable Bonds: 5

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.65

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -2.06

References

1. Perez C, Li J, Parlati F, Rouffet M, Ma Y, Mackinnon AL, Chou TF, Deshaies RJ, Cohen SM..  (2017)  Discovery of an Inhibitor of the Proteasome Subunit Rpn11.,  60  (4): [PMID:28191850] [10.1021/acs.jmedchem.6b01379]

2. Perez, Christian C and 8 more authors.  2017-02-23  Discovery of an Inhibitor of the Proteasome Subunit Rpn11.  [PMID:28191850]

Source

Source(1):

• Scientific Literature