N-(3-fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

ID: ALA3104406

PubChem CID: 54742333

Max Phase: Preclinical

Molecular Formula: C17H14FN3O3S

Molecular Weight: 359.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(-n2ccc(O)cc2=O)sc1C(=O)NCc1cccc(F)c1

Standard InChI:  InChI=1S/C17H14FN3O3S/c1-10-15(16(24)19-9-11-3-2-4-12(18)7-11)25-17(20-10)21-6-5-13(22)8-14(21)23/h2-8,22H,9H2,1H3,(H,19,24)

Standard InChI Key:  BHUCOKRFLNIIRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.6808  -19.2127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9881  -18.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9689  -17.9611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1845  -17.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7221  -18.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2223  -19.0513    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9111  -16.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9052  -18.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4765  -17.7316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5171  -19.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6597  -17.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2309  -17.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6219  -16.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1939  -15.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3761  -15.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9883  -16.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4186  -17.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6461  -20.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3346  -20.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0588  -20.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0903  -19.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3975  -18.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4268  -18.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7497  -20.5204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1715  -16.4205    0.0000 F   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
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 22  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104406

   N-(3-Fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-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: 359.38

Molecular Weight (Monoisotopic): 359.0740

AlogP: 2.38

#Rotatable Bonds: 4

Polar Surface Area: 84.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.61

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.90

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