N-benzyl-2-(3-benzylisoxazol-5-yl)-4-methylthiazole-5-carboxamide

ID: ALA3104611

PubChem CID: 24960062

Max Phase: Preclinical

Molecular Formula: C22H19N3O2S

Molecular Weight: 389.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(-c2cc(Cc3ccccc3)no2)sc1C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C22H19N3O2S/c1-15-20(21(26)23-14-17-10-6-3-7-11-17)28-22(24-15)19-13-18(25-27-19)12-16-8-4-2-5-9-16/h2-11,13H,12,14H2,1H3,(H,23,26)

Standard InChI Key:  VVCCFRMGZHTIFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.9157   -6.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6237   -6.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3334   -6.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3305   -5.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6219   -4.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0417   -6.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7488   -6.1244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4571   -6.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1642   -6.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4584   -7.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9069   -6.4546    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4527   -5.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0430   -5.1393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2440   -5.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6344   -4.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2671   -5.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6769   -6.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4759   -6.4607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5601   -5.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8130   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2671   -5.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9755   -5.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9720   -6.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6795   -6.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3875   -6.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3835   -5.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6754   -5.2327    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
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 10  2  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 13 17  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104611

   N-benzyl-2-(3-benzylisoxazol-5-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: 389.48

Molecular Weight (Monoisotopic): 389.1198

AlogP: 4.63

#Rotatable Bonds: 6

Polar Surface Area: 68.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.81

References

1. 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