6-Methyl-N-(4-methylthiazol-2-yl)-4-(pyrimidin-5-yloxy)-picolinamide

ID: ALA4089038

PubChem CID: 137643022

Max Phase: Preclinical

Molecular Formula: C15H13N5O2S

Molecular Weight: 327.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Oc2cncnc2)cc(C(=O)Nc2nc(C)cs2)n1

Standard InChI:  InChI=1S/C15H13N5O2S/c1-9-3-11(22-12-5-16-8-17-6-12)4-13(18-9)14(21)20-15-19-10(2)7-23-15/h3-8H,1-2H3,(H,19,20,21)

Standard InChI Key:  SGRIDZXLXCGMAU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.0156  -19.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144  -20.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225  -21.1506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4321  -20.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293  -19.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7207  -19.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064  -21.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7183  -18.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247  -18.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1316  -18.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8376  -18.2842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8356  -17.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1217  -17.0598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186  -17.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405  -21.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418  -21.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8476  -20.7389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5559  -21.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407  -21.9571    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4403  -22.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8479  -21.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000  -20.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6604  -21.3306    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
  2  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089038

   ---

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: 327.37

Molecular Weight (Monoisotopic): 327.0790

AlogP: 2.99

#Rotatable Bonds: 4

Polar Surface Area: 89.89

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 2.01

CX LogP: 1.42

CX LogD: 1.42

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -1.89

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