2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylpyrazin-2-yl)methyl)thiazole-5-carboxamide

ID: ALA3104411

PubChem CID: 57744457

Max Phase: Preclinical

Molecular Formula: C16H15N5O3S

Molecular Weight: 357.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc(CNC(=O)c2sc(-n3ccc(O)cc3=O)nc2C)cn1

Standard InChI:  InChI=1S/C16H15N5O3S/c1-9-6-18-11(7-17-9)8-19-15(24)14-10(2)20-16(25-14)21-4-3-12(22)5-13(21)23/h3-7,22H,8H2,1-2H3,(H,19,24)

Standard InChI Key:  BVGDWOAIZUYMOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   16.2751  -18.3212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5783  -17.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5591  -17.0655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7705  -16.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3082  -17.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8084  -18.1598    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4972  -16.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4872  -17.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0543  -16.8360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0949  -18.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2333  -16.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046  -16.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2404  -19.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9330  -19.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6614  -19.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6929  -18.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9960  -17.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0253  -17.1158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3564  -19.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1956  -15.4384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7634  -14.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9416  -14.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5537  -15.4903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9882  -16.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5111  -14.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  2  3  2  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  4  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
  1 13  1  0
  1 17  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 15 19  1  0
 12 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 12  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104411

   2-(4-Hydroxy-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylpyrazin-2-yl)methyl)thiazole-5-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: 357.40

Molecular Weight (Monoisotopic): 357.0896

AlogP: 1.34

#Rotatable Bonds: 4

Polar Surface Area: 110.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.61

CX Basic pKa: 1.06

CX LogP: -0.32

CX LogD: -0.53

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.65

References

1. Sun S, Zhang Z, Raina V, Pokrovskaia N, Hou D, Namdari R, Khakh K, Ratkay LG, McLaren DG, Mork M, Fu J, Ferreira S, Hubbard B, Winther MD, Dales N..  (2014)  Discovery of thiazolylpyridinone SCD1 inhibitors with preferential liver distribution and reduced mechanism-based adverse effects.,  24  (2): [PMID:24370012] [10.1016/j.bmcl.2013.12.035]

Source

Source(1):

• Scientific Literature