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

ID: ALA4284015

PubChem CID: 25099435

Max Phase: Preclinical

Molecular Formula: C23H27N3O3S2

Molecular Weight: 457.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1ccccc1NCc1ccc(C(=O)Nc2nc(CC(=O)O)cs2)s1

Standard InChI:  InChI=1S/C23H27N3O3S2/c1-2-3-4-5-8-16-9-6-7-10-19(16)24-14-18-11-12-20(31-18)22(29)26-23-25-17(15-30-23)13-21(27)28/h6-7,9-12,15,24H,2-5,8,13-14H2,1H3,(H,27,28)(H,25,26,29)

Standard InChI Key:  YNWGCQBJZMOQPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   24.8534   -3.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5683   -3.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2848   -3.5677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5641   -2.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9972   -3.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7490   -3.4847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2979   -2.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8817   -2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0757   -2.3322    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0934   -3.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5428   -3.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9616   -4.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7709   -4.4049    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.6309   -5.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8109   -5.4296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4802   -6.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6609   -6.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3301   -7.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8194   -7.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6433   -7.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9702   -6.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1727   -5.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3526   -5.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8658   -5.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0455   -5.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588   -4.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7386   -4.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1188   -2.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6003   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4212   -2.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2610   -1.5291    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
  7 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4284015

   2-[2-[[5-[(2-Hexylanilino)methyl]thiophene-2-carbonyl]amino]-1,3-thiazol-4-yl]acetic acid

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: 457.62

Molecular Weight (Monoisotopic): 457.1494

AlogP: 5.82

#Rotatable Bonds: 12

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: 5.66

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -1.70

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