SB-657836-AAA

ID: ALA1909342

PubChem CID: 16236469

Max Phase: Preclinical

Molecular Formula: C17H21N3O6S

Molecular Weight: 305.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SB-657836-AAA | SB-657836AAA | SB-657836-AAA|CHEMBL1909342|SB-657836AAA|HMS3303C14|HMS3305G07|AKOS001035059|N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-y|F0239-0482

Canonical SMILES:  N#Cc1c(NC(=O)CN2CCOCC2)sc2c1CCCC2.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C15H19N3O2S.C2H2O4/c16-9-12-11-3-1-2-4-13(11)21-15(12)17-14(19)10-18-5-7-20-8-6-18;3-1(4)2(5)6/h1-8,10H2,(H,17,19);(H,3,4)(H,5,6)

Standard InChI Key:  GLZXTMBTCQJTRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    6.1580   -0.5048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.5048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -1.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830   -1.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -1.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830   -0.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1580    0.9241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830    0.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4680    1.5916    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2526    1.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9671    1.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815    1.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815    0.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9671    0.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2526    0.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4680    0.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2130   -0.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9581   -1.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 18  2  0
 18 19  1  0
 11 19  2  0
 19 20  1  0
 20 21  3  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  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: 305.40

Molecular Weight (Monoisotopic): 305.1198

AlogP: 1.77

#Rotatable Bonds: 3

Polar Surface Area: 65.36

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.24

CX Basic pKa: 4.36

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.92

Np Likeness Score: -2.96

References

1. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

2. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

3. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

Source

Source(1):

• GSK Published Kinase Inhibitor Set