2-chloro-4-hydroxy-3-isopropyl-5-(3-phenoxyphenyl)thieno[2,3-b]pyridin-6(7H)-one

ID: ALA201440

Chembl Id: CHEMBL201440

PubChem CID: 54715302

Max Phase: Preclinical

Molecular Formula: C22H18ClNO3S

Molecular Weight: 411.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1c(Cl)sc2nc(O)c(-c3cccc(Oc4ccccc4)c3)c(O)c12

Standard InChI:  InChI=1S/C22H18ClNO3S/c1-12(2)16-18-19(25)17(21(26)24-22(18)28-20(16)23)13-7-6-10-15(11-13)27-14-8-4-3-5-9-14/h3-12H,1-2H3,(H2,24,25,26)

Standard InChI Key:  QNBWBOVXXZTOCG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA201440

   2-chloro-4-hydroxy-5-(3-phenoxyphenyl)-3-propan-2-yl-7H-thieno[2,3-b]pyridin-6-one

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: 411.91

Molecular Weight (Monoisotopic): 411.0696

AlogP: 6.94

#Rotatable Bonds: 4

Polar Surface Area: 62.58

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.37

CX Basic pKa: ┄

CX LogP: 7.15

CX LogD: 7.14

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -0.39

References

1. Buchstaller HP, Siebert CD, Steinmetz R, Frank I, Berger ML, Gottschlich R, Leibrock J, Krug M, Steinhilber D, Noe CR..  (2006)  Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [3H]glycine binding to the N-methyl-D-aspartate (NMDA) receptor.,  49  (3): [PMID:16451052] [10.1021/jm0503493]

Source

Source(1):

• Scientific Literature