3-(1-cyclopentyl-1H-benzo[d][1,2,3]triazol-5-yl)-5-(4-fluorophenyl)-1,2,4-oxadiazole

ID: ALA3735905

PubChem CID: 22583268

Max Phase: Preclinical

Molecular Formula: C19H16FN5O

Molecular Weight: 349.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(-c2nc(-c3ccc4c(c3)nnn4C3CCCC3)no2)cc1

Standard InChI:  InChI=1S/C19H16FN5O/c20-14-8-5-12(6-9-14)19-21-18(23-26-19)13-7-10-17-16(11-13)22-24-25(17)15-3-1-2-4-15/h5-11,15H,1-4H2

Standard InChI Key:  LRRVNQIIXFMMNH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
    2.1749    2.6315    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.8711    0.0000 N   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
    1.3751    3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    5.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    2.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 10 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735905

   1-cyclopentyl-5-[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]-1H-1,2,3-benzotriazole

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: 349.37

Molecular Weight (Monoisotopic): 349.1339

AlogP: 4.40

#Rotatable Bonds: 3

Polar Surface Area: 69.63

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.15

CX LogP: 4.95

CX LogD: 4.95

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -2.15

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