5-((3-bromo-10-methyl-9H-benzo[f]imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]diazepin-6-yl)methyl)-3-methyl-1,2,4-oxadiazole

ID: ALA1081861

PubChem CID: 16117222

Max Phase: Preclinical

Molecular Formula: C17H14BrN7O

Molecular Weight: 412.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1noc(Cc2nc3n(n2)Cc2c(C)ncn2-c2ccc(Br)cc2-3)n1

Standard InChI:  InChI=1S/C17H14BrN7O/c1-9-14-7-25-17(21-15(22-25)6-16-20-10(2)23-26-16)12-5-11(18)3-4-13(12)24(14)8-19-9/h3-5,8H,6-7H2,1-2H3

Standard InChI Key:  GCTGWUUTZLTQAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   -5.4678  -12.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783  -13.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801  -11.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901  -12.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882  -12.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407  -11.6450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286  -11.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395  -11.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111  -10.4678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5534  -10.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802  -13.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4030  -13.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4762  -14.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987  -14.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449  -14.0548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500  -10.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1661  -13.3699    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023  -15.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727  -15.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852  -16.7991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598  -16.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6342  -16.2486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967  -15.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196  -17.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  8  1  0
 13 14  1  0
  3  6  2  0
  5  9  1  0
  5 13  1  0
 14  6  1  0
  6  7  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  7  8  1  0
 10 18  1  0
  8  9  1  0
  2 19  1  0
  1  2  2  0
 16 20  1  0
  7  4  2  0
 20 21  1  0
 21 22  2  0
  4  1  1  0
  2  3  1  0
  9 10  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 10 11  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081861

   5-[(15-Bromo-5-methyl-2,4,8,9,11-pentazatetracyclo[11.4.0.02,6.08,12]heptadeca-1(13),3,5,9,11,14,16-heptaen-10-yl)methyl]-3-methyl-1,2,4-oxadiazole

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: 412.25

Molecular Weight (Monoisotopic): 411.0443

AlogP: 2.85

#Rotatable Bonds: 2

Polar Surface Area: 87.45

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.41

CX Basic pKa: 4.69

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -1.56

References

1. Buettelmann B, Ballard TM, Gasser R, Fischer H, Hernandez MC, Knoflach F, Knust H, Stadler H, Thomas AW, Trube G..  (2009)  Imidazo[1,5-a][1,2,4]-triazolo[1,5-d][1,4]benzodiazepines as potent and highly selective GABAA alpha5 inverse agonists with potential for the treatment of cognitive dysfunction.,  19  (20): [PMID:19740657] [10.1016/j.bmcl.2009.08.027]

Source

Source(1):

• Scientific Literature