2-(5-chloro-2-(3-(4-fluorophenylthio)-6-(pyridin-2-ylthio)picolinamido)thiazol-4-yl)acetic acid

ID: ALA4065127

PubChem CID: 76900521

Max Phase: Preclinical

Molecular Formula: C22H14ClFN4O3S3

Molecular Weight: 533.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1nc(NC(=O)c2nc(Sc3ccccn3)ccc2Sc2ccc(F)cc2)sc1Cl

Standard InChI:  InChI=1S/C22H14ClFN4O3S3/c23-20-14(11-18(29)30)26-22(34-20)28-21(31)19-15(32-13-6-4-12(24)5-7-13)8-9-17(27-19)33-16-3-1-2-10-25-16/h1-10H,11H2,(H,29,30)(H,26,28,31)

Standard InChI Key:  KOPZKACIIKMKDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   29.0955   -3.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0944   -4.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8024   -4.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5121   -4.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5093   -3.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8007   -2.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3877   -2.8438    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.6801   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2205   -4.4788    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.2217   -5.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5134   -5.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5143   -6.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2232   -6.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9326   -6.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9282   -5.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2256   -7.7460    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.2154   -2.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9247   -3.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2124   -2.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6308   -2.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3779   -3.1604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9225   -2.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5112   -1.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7125   -2.0179    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.9724   -2.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2653   -3.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2651   -4.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9778   -4.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6821   -4.0664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7355   -2.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2133   -1.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0264   -2.0528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8781   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8407   -1.0970    0.0000 Cl  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
  1  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
  5 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  8 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29  8  1  0
 22 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 23 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4065127

   2-[5-Chloro-2-[[3-(4-fluorophenyl)sulfanyl-6-pyridin-2-ylsulfanylpyridine-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: 533.03

Molecular Weight (Monoisotopic): 531.9901

AlogP: 5.91

#Rotatable Bonds: 8

Polar Surface Area: 105.07

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.18

CX Basic pKa: 2.28

CX LogP: 6.52

CX LogD: 3.40

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.29

Np Likeness Score: -1.69

References

1. Xu J, Lin S, Myers RW, Trujillo ME, Pachanski MJ, Malkani S, Chen HS, Chen Z, Campbell B, Eiermann GJ, Elowe N, Farrer BT, Feng W, Fu Q, Kats-Kagan R, Kavana M, McMasters DR, Mitra K, Tong X, Xu L, Zhang F, Zhang R, Addona GH, Berger JP, Zhang B, Parmee ER..  (2017)  Discovery of orally active hepatoselective glucokinase activators for treatment of Type II Diabetes Mellitus.,  27  (9): [PMID:28284809] [10.1016/j.bmcl.2016.10.088]

Source

Source(1):

• Scientific Literature