4-((5-Fluoropyridin-3-yl)oxy)-6-methyl-N-(4-methylthiazol-2-yl)-picolinamide

ID: ALA4093386

PubChem CID: 137653256

Max Phase: Preclinical

Molecular Formula: C16H13FN4O2S

Molecular Weight: 344.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Oc2cncc(F)c2)cc(C(=O)Nc2nc(C)cs2)n1

Standard InChI:  InChI=1S/C16H13FN4O2S/c1-9-3-12(23-13-4-11(17)6-18-7-13)5-14(19-9)15(22)21-16-20-10(2)8-24-16/h3-8H,1-2H3,(H,20,21,22)

Standard InChI Key:  LXFZGMMUMWNUIT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.5466  -11.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5454  -12.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2535  -12.6733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9631  -12.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9603  -11.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2517  -11.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2492  -10.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9557   -9.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6625  -10.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3685   -9.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3665   -8.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6526   -8.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9496   -8.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6715  -12.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6728  -13.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3785  -12.2616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0869  -12.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1717  -13.4798    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.9713  -13.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3788  -12.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8310  -12.3337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1914  -12.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6473   -7.7653    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.8374  -12.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 20 22  1  0
 12 23  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093386

   ---

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: 344.37

Molecular Weight (Monoisotopic): 344.0743

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 77.00

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 2.67

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -2.13

References

1. Felts AS, Rodriguez AL, Blobaum AL, Morrison RD, Bates BS, Thompson Gray A, Rook JM, Tantawy MN, Byers FW, Chang S, Venable DF, Luscombe VB, Tamagnan GD, Niswender CM, Daniels JS, Jones CK, Conn PJ, Lindsley CW, Emmitte KA..  (2017)  Discovery of N-(5-Fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (VU0424238): A Novel Negative Allosteric Modulator of Metabotropic Glutamate Receptor Subtype 5 Selected for Clinical Evaluation.,  60  (12): [PMID:28530802] [10.1021/acs.jmedchem.7b00410]

Source

Source(1):

• Scientific Literature