(S)-3-(1-(2-chlorophenyl)ethoxy)-5-(6-((1-methylpiperidin-4-yl)methoxy)-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxamide

ID: ALA1794069

Chembl Id: CHEMBL1794069

PubChem CID: 25263124

Max Phase: Preclinical

Molecular Formula: C27H29ClN4O3S

Molecular Weight: 525.07

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK571989A | GSK571989A|CHEMBL1794069|BDBM28214|HMS3304F01|HMS3305O14|NSC756178|NSC-756178|benzimidazole thiophene carboxamide, 22|AB01092181-01|3-[(1R)-1-(2-chlorophenyl)ethoxy]-5-{6-[(1-methylpiperidin-4-yl)methoxy]-1H-1,3-benzodiazol-1-yl}thiophene-2-carboxamide

Canonical SMILES:  C[C@@H](Oc1cc(-n2cnc3ccc(OCC4CCN(C)CC4)cc32)sc1C(N)=O)c1ccccc1Cl

Standard InChI:  InChI=1S/C27H29ClN4O3S/c1-17(20-5-3-4-6-21(20)28)35-24-14-25(36-26(24)27(29)33)32-16-30-22-8-7-19(13-23(22)32)34-15-18-9-11-31(2)12-10-18/h3-8,13-14,16-18H,9-12,15H2,1-2H3,(H2,29,33)/t17-/m1/s1

Standard InChI Key:  FCJBLTLQBCHRIE-QGZVFWFLSA-N

Alternative Forms

1. Parent:

   

   ALA1794069

   GSK-571989A

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: 525.07

Molecular Weight (Monoisotopic): 524.1649

AlogP: 5.70

#Rotatable Bonds: 8

Polar Surface Area: 82.61

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.93

CX Basic pKa: 9.18

CX LogP: 4.99

CX LogD: 3.21

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: -1.13

References

1. Emmitte KA, Adjabeng GM, Andrews CW, Alberti JG, Bambal R, Chamberlain SD, Davis-Ward RG, Dickson HD, Hassler DF, Hornberger KR, Jackson JR, Kuntz KW, Lansing TJ, Mook RA, Nailor KE, Pobanz MA, Smith SC, Sung CM, Cheung M..  (2009)  Design of potent thiophene inhibitors of polo-like kinase 1 with improved solubility and reduced protein binding.,  19  (6): [PMID:19237286] [10.1016/j.bmcl.2009.01.094]

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

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

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

Source

Source(2):

• Scientific Literature
• GSK Published Kinase Inhibitor Set