3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide

ID: ALA207012

Chembl Id: CHEMBL207012

Cas Number: 55557-48-7

PubChem CID: 359052

Max Phase: Preclinical

Molecular Formula: C8H7N3OS

Molecular Weight: 193.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2ncccc2c1N

Standard InChI:  InChI=1S/C8H7N3OS/c9-5-4-2-1-3-11-8(4)13-6(5)7(10)12/h1-3H,9H2,(H2,10,12)

Standard InChI Key:  XZIZYTUIRQMBPN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA207012

   3-Aminothieno[2,3-b]pyridine-2-carboxamide

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: 193.23

Molecular Weight (Monoisotopic): 193.0310

AlogP: 0.98

#Rotatable Bonds: 1

Polar Surface Area: 82.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.10

CX LogP: 0.80

CX LogD: 0.80

Aromatic Rings: 2

Heavy Atoms: 13

QED Weighted: 0.71

Np Likeness Score: -2.10

References

1. Morwick T, Berry A, Brickwood J, Cardozo M, Catron K, DeTuri M, Emeigh J, Homon C, Hrapchak M, Jacober S, Jakes S, Kaplita P, Kelly TA, Ksiazek J, Liuzzi M, Magolda R, Mao C, Marshall D, McNeil D, Prokopowicz A, Sarko C, Scouten E, Sledziona C, Sun S, Watrous J, Wu JP, Cywin CL..  (2006)  Evolution of the thienopyridine class of inhibitors of IkappaB kinase-beta: part I: hit-to-lead strategies.,  49  (10): [PMID:16686533] [10.1021/jm0510979]

2. Sleebs BE, Nikolakopoulos G, Street IP, Falk H, Baell JB..  (2011)  Identification of 5,6-substituted 4-aminothieno[2,3-d]pyrimidines as LIMK1 inhibitors.,  21  (19): [PMID:21852129] [10.1016/j.bmcl.2011.07.050]

3. Sleebs BE, Levit A, Street IP, Falk H, Hammonds T, Wong AC, Charles MD, Olson MF, Baell JB.  (2011)  Identification of 3-aminothieno[2,3-b]pyridine-2-carboxamides and 4-aminobenzothieno[3,2-d]pyrimidines as LIMK1 inhibitors,  2  (10): [10.1039/C1MD00137J]

4. Sleebs BE, Ganame D, Levit A, Street IP, Gregg A, Falk H, Baell JB.  (2011)  Development of substituted 7-phenyl-4-aminobenzothieno[3,2-d] pyrimidines as potent LIMK1 inhibitors,  2  (10): [10.1039/C1MD00138H]

5. Manetti F..  (2018)  Recent advances in the rational design and development of LIM kinase inhibitors are not enough to enter clinical trials.,  155  [PMID:29908439] [10.1016/j.ejmech.2018.06.016]

Source

Source(1):

• Scientific Literature