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

ID: ALA3104408

PubChem CID: 54742336

Max Phase: Preclinical

Molecular Formula: C18H16FN3O3S

Molecular Weight: 373.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(-n2ccc(O)cc2=O)sc1C(=O)NCCc1ccc(F)cc1

Standard InChI:  InChI=1S/C18H16FN3O3S/c1-11-16(17(25)20-8-6-12-2-4-13(19)5-3-12)26-18(21-11)22-9-7-14(23)10-15(22)24/h2-5,7,9-10,23H,6,8H2,1H3,(H,20,25)

Standard InChI Key:  HGWXLMRDZPZHIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  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
   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
    9.9940  -16.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1824  -16.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7989  -17.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2330  -17.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0431  -17.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9822  -17.1693    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
 13 12  1  0
  1 14  1  0
  1 18  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 16 20  1  0
 13 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 13  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104408

   N-(4-Fluorophenethyl)-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: 373.41

Molecular Weight (Monoisotopic): 373.0896

AlogP: 2.42

#Rotatable Bonds: 5

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: 2.34

CX LogD: 2.13

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.50

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