8-ethynyl-6-(pyridin-2-yl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid

ID: ALA2332214

Chembl Id: CHEMBL2332214

PubChem CID: 21930927

Max Phase: Preclinical

Molecular Formula: C19H12N4O2

Molecular Weight: 328.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc2c(c1)C(c1ccccn1)=NCc1c(C(=O)O)ncn1-2

Standard InChI:  InChI=1S/C19H12N4O2/c1-2-12-6-7-15-13(9-12)17(14-5-3-4-8-20-14)21-10-16-18(19(24)25)22-11-23(15)16/h1,3-9,11H,10H2,(H,24,25)

Standard InChI Key:  LNWKMCTYBSXUHQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2332214

   8-ethynyl-6-pyridin-2-yl-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

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: 328.33

Molecular Weight (Monoisotopic): 328.0960

AlogP: 2.30

#Rotatable Bonds: 2

Polar Surface Area: 80.37

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.80

CX Basic pKa: 3.63

CX LogP: 1.75

CX LogD: -0.98

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.82

References

1. Namjoshi OA, Wang ZJ, Rallapalli SK, Johnson EM, Johnson YT, Ng H, Ramerstorfer J, Varagic Z, Sieghart W, Majumder S, Roth BL, Rowlett JK, Cook JM..  (2013)  Search for α3β₂/₃γ2 subtype selective ligands that are stable on human liver microsomes.,  21  (1): [PMID:23218469] [10.1016/j.bmc.2012.10.057]

2. Poe MM, Methuku KR, Li G, Verma AR, Teske KA, Stafford DC, Arnold LA, Cramer JW, Jones TM, Cerne R, Krambis MJ, Witkin JM, Jambrina E, Rehman S, Ernst M, Cook JM, Schkeryantz JM..  (2016)  Synthesis and Characterization of a Novel γ-Aminobutyric Acid Type A (GABAA) Receptor Ligand That Combines Outstanding Metabolic Stability, Pharmacokinetics, and Anxiolytic Efficacy.,  59  (23): [PMID:27933953] [10.1021/acs.jmedchem.6b01332]

Source

Source(1):

• Scientific Literature