2-(5-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-4,5,6,7-tetrahydro-1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropanenitrile

ID: ALA3735720

PubChem CID: 127034894

Max Phase: Preclinical

Molecular Formula: C18H17FN6O

Molecular Weight: 352.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C#N)n1nnc2c1CCC(c1nc(-c3ccc(F)cc3)no1)C2

Standard InChI:  InChI=1S/C18H17FN6O/c1-18(2,10-20)25-15-8-5-12(9-14(15)22-24-25)17-21-16(23-26-17)11-3-6-13(19)7-4-11/h3-4,6-7,12H,5,8-9H2,1-2H3

Standard InChI Key:  GXCVAGOKZOYKBO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168   -1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580   -2.9756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730   -1.9836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8393   -4.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0560   -5.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -7.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2699   -7.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0549   -6.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3406   -4.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8414   -8.3424    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    2.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    3.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    3.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203    3.1886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  3 10  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  9 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 23 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735720

   ---

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: 352.37

Molecular Weight (Monoisotopic): 352.1448

AlogP: 3.00

#Rotatable Bonds: 3

Polar Surface Area: 93.42

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.75

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.78

References

1. Ellard JM, Madin A, Philps O, Hopkin M, Henderson S, Birch L, O'Connor D, Arai T, Takase K, Morgan L, Reynolds D, Talma S, Howley E, Powney B, Payne AH, Hall A, Gartlon JE, Dawson LA, Castro L, Atkinson PJ..  (2015)  Identification and optimisation of a series of tetrahydrobenzotriazoles as metabotropic glutamate receptor 5-selective positive allosteric modulators that improve performance in a preclinical model of cognition.,  25  (24): [PMID:26531152] [10.1016/j.bmcl.2015.10.050]

Source

Source(1):

• Scientific Literature