2-(4-Methoxy-phenyl)-5H-3,3a,5,9b-tetraaza-cyclopenta[a]naphthalene-1,4-dione

ID: ALA192554

Chembl Id: CHEMBL192554

PubChem CID: 11255271

Max Phase: Preclinical

Molecular Formula: C16H12N4O3

Molecular Weight: 308.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nn3c(=O)[nH]c4ccccc4n3c2=O)cc1

Standard InChI:  InChI=1S/C16H12N4O3/c1-23-11-8-6-10(7-9-11)14-15(21)19-13-5-3-2-4-12(13)17-16(22)20(19)18-14/h2-9H,1H3,(H,17,22)

Standard InChI Key:  PKJGSRHYDOGGLB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA192554

   2-(4-methoxyphenyl)-6H-triazolo[1,2-a][1,2,4]benzotriazine-1,5-dione

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: 308.30

Molecular Weight (Monoisotopic): 308.0909

AlogP: 1.31

#Rotatable Bonds: 2

Polar Surface Area: 80.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.51

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: -0.72

References

1. Primofiore G, Da Settimo F, Taliani S, Salerno S, Novellino E, Greco G, Cosimelli B, Besnard F, Costa B, Montali M, Martini C..  (2005)  High affinity central benzodiazepine receptor ligands: synthesis and biological evaluation of a series of phenyltriazolobenzotriazindione derivatives.,  48  (8): [PMID:15828832] [10.1021/jm0408722]

2. Da Settimo F, Primofiore G, Taliani S, Marini AM, La Motta C, Simorini F, Salerno S, Sergianni V, Tuccinardi T, Martinelli A, Cosimelli B, Greco G, Novellino E, Ciampi O, Trincavelli ML, Martini C..  (2007)  5-amino-2-phenyl[1,2,3]triazolo[1,2-a][1,2,4]benzotriazin-1-one: a versatile scaffold to obtain potent and selective A3 adenosine receptor antagonists.,  50  (23): [PMID:17927167] [10.1021/jm0708376]

Source

Source(1):

• Scientific Literature