N-(5-fluoropyridin-2-yl)-6-(5-fluoropyridin-3-yloxy)-3-methyl-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide

ID: ALA4094617

PubChem CID: 118104069

Max Phase: Preclinical

Molecular Formula: C18H12F2N6O2

Molecular Weight: 382.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc2c(C(=O)Nc3ccc(F)cn3)cc(Oc3cncc(F)c3)cn12

Standard InChI:  InChI=1S/C18H12F2N6O2/c1-10-24-25-17-15(18(27)23-16-3-2-11(19)7-22-16)5-14(9-26(10)17)28-13-4-12(20)6-21-8-13/h2-9H,1H3,(H,22,23,27)

Standard InChI Key:  WBWHBHWEZVQLRK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   21.4602  -12.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8767  -13.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8739  -12.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1653  -12.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1671  -14.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4593  -13.7655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8545  -14.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1885  -15.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9997  -14.9700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1628  -11.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8693  -11.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5761  -11.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2821  -11.3050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2801  -10.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5662  -10.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8632  -10.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5609   -9.2635    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5851  -14.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5864  -14.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2921  -13.7598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0005  -14.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9972  -14.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7047  -15.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4127  -14.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4088  -14.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7007  -13.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1216  -15.3871    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.0547  -14.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  5  2  1  0
  2  3  2  0
  3  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
  7 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094617

   N-(5-fluoropyridin-2-yl)-6-(5-fluoropyridin-3-yl)oxy-3-methyl-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide

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: 382.33

Molecular Weight (Monoisotopic): 382.0990

AlogP: 3.15

#Rotatable Bonds: 4

Polar Surface Area: 94.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: 2.51

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.76

References

1. Felts AS, Rodriguez AL, Morrison RD, Bollinger KA, Venable DF, Blobaum AL, Byers FW, Thompson Gray A, Daniels JS, Niswender CM, Jones CK, Conn PJ, Lindsley CW, Emmitte KA..  (2017)  Discovery of imidazo[1,2-a]-, [1,2,4]triazolo[4,3-a]-, and [1,2,4]triazolo[1,5-a]pyridine-8-carboxamide negative allosteric modulators of metabotropic glutamate receptor subtype 5.,  27  (21): [PMID:28958625] [10.1016/j.bmcl.2017.09.042]

Source

Source(1):

• Scientific Literature