2-benzamido-4-methyl-N-phenylthiazole-5-carboxamide

ID: ALA3104387

PubChem CID: 860667

Max Phase: Preclinical

Molecular Formula: C18H15N3O2S

Molecular Weight: 337.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(NC(=O)c2ccccc2)sc1C(=O)Nc1ccccc1

Standard InChI:  InChI=1S/C18H15N3O2S/c1-12-15(17(23)20-14-10-6-3-7-11-14)24-18(19-12)21-16(22)13-8-4-2-5-9-13/h2-11H,1H3,(H,20,23)(H,19,21,22)

Standard InChI Key:  VUPOVEVEJLSSRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    0.5434  -25.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422  -26.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503  -26.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599  -26.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571  -25.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485  -24.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633  -24.8190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725  -25.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0787  -24.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3756  -26.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258  -25.1420    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3703  -24.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9590  -23.8264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604  -23.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833  -24.6150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5185  -25.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3315  -25.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0407  -26.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6622  -26.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4745  -26.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9532  -25.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6139  -24.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8026  -24.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507  -23.4553    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
  5  7  1  0
  7  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  9  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104387

   2-benzamido-4-methyl-N-phenyl-1,3-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: 337.40

Molecular Weight (Monoisotopic): 337.0885

AlogP: 3.96

#Rotatable Bonds: 4

Polar Surface Area: 71.09

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -1.95

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]

2. Sun S, Zhang Z, Kodumuru V, Pokrovskaia N, Fonarev J, Jia Q, Leung PY, Tran J, Ratkay LG, McLaren DG, Radomski C, Chowdhury S, Fu J, Hubbard B, Winther MD, Dales NA..  (2014)  Systematic evaluation of amide bioisosteres leading to the discovery of novel and potent thiazolylimidazolidinone inhibitors of SCD1 for the treatment of metabolic diseases.,  24  (2): [PMID:24374272] [10.1016/j.bmcl.2013.12.036]

Source

Source(1):

• Scientific Literature