Sodium [2-({5-[(2-octyl-phenylamino)-methyl]-thiophene-2-carbonyl}-amino)-thiazol-4-yl]-acetate

ID: ALA4291877

PubChem CID: 145485632

Max Phase: Preclinical

Molecular Formula: C25H31N3O3S2

Molecular Weight: 485.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCc1ccccc1NCc1ccc(C(=O)Nc2nc(CC(=O)O)cs2)s1

Standard InChI:  InChI=1S/C25H31N3O3S2/c1-2-3-4-5-6-7-10-18-11-8-9-12-21(18)26-16-20-13-14-22(33-20)24(31)28-25-27-19(17-32-25)15-23(29)30/h8-9,11-14,17,26H,2-7,10,15-16H2,1H3,(H,29,30)(H,27,28,31)

Standard InChI Key:  BBZBQWFAPYWGBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   25.2284   -9.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9434   -9.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6599   -9.6884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9392   -8.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3722   -9.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1241   -9.6053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6730   -8.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2569   -8.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4509   -8.4528    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.4685   -9.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9180   -9.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3367  -10.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1460  -10.5256    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0059  -11.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1861  -11.5502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8552  -12.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0360  -12.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7052  -13.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1944  -13.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0183  -13.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3453  -12.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5478  -11.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7276  -11.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2408  -11.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4207  -11.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9339  -10.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1136  -10.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6268   -9.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8067  -10.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4939   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9755   -8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7964   -8.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6361   -7.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  1  2  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  1 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  1  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  7 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4291877

   ---

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: 485.68

Molecular Weight (Monoisotopic): 485.1807

AlogP: 6.60

#Rotatable Bonds: 14

Polar Surface Area: 91.32

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.01

CX Basic pKa: 3.64

CX LogP: 6.55

CX LogD: 3.86

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: -1.60

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