[2-(4-{[2-(3-Methyl-butyl)-phenylamino]-methyl}-benzoylamino)-thiazol-4-yl]-acetic acid

ID: ALA4286817

PubChem CID: 145488943

Max Phase: Preclinical

Molecular Formula: C24H27N3O3S

Molecular Weight: 437.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCc1ccccc1NCc1ccc(C(=O)Nc2nc(CC(=O)O)cs2)cc1

Standard InChI:  InChI=1S/C24H27N3O3S/c1-16(2)7-10-18-5-3-4-6-21(18)25-14-17-8-11-19(12-9-17)23(30)27-24-26-20(15-31-24)13-22(28)29/h3-6,8-9,11-12,15-16,25H,7,10,13-14H2,1-2H3,(H,28,29)(H,26,27,30)

Standard InChI Key:  SZPIDKVNLJYYCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   19.0191  -12.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0179  -13.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7328  -13.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4492  -13.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4463  -12.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7310  -12.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1593  -12.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8752  -12.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5882  -12.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3026  -12.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0149  -12.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0123  -11.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2913  -10.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5818  -11.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7273  -10.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4438  -11.2553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7230  -10.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1562  -10.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9080  -11.1722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4569  -10.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0407   -9.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2347  -10.0196    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7285  -11.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0128  -10.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0104  -10.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7236   -9.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2947   -9.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2778  -10.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7593   -9.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5802  -10.0505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4199   -9.2165    0.0000 O   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
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  1  0
 15 17  2  0
 12 15  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  6 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4286817

   ---

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: 437.57

Molecular Weight (Monoisotopic): 437.1773

AlogP: 5.22

#Rotatable Bonds: 10

Polar Surface Area: 91.32

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.33

CX Basic pKa: 3.96

CX LogP: 4.99

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.43

References

1. Iida T, Ubukata M, Mitani I, Nakagawa Y, Maeda K, Imai H, Ogoshi Y, Hotta T, Sakata S, Sano R, Morinaga H, Negoro T, Oshida S, Tanaka M, Inaba T..  (2018)  Discovery of potent liver-selective stearoyl-CoA desaturase-1 (SCD1) inhibitors, thiazole-4-acetic acid derivatives, for the treatment of diabetes, hepatic steatosis, and obesity.,  158  [PMID:30248655] [10.1016/j.ejmech.2018.09.003]

Source

Source(1):

• Scientific Literature