2-(2-(3-(4-methoxyphenylthio)-6-(4-methyl-4H-1,2,4-triazol-3-ylthio)picolinamido)thiazol-5-ylthio)acetic acid

ID: ALA4062363

PubChem CID: 76902401

Max Phase: Preclinical

Molecular Formula: C21H18N6O4S4

Molecular Weight: 546.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Sc2ccc(Sc3nncn3C)nc2C(=O)Nc2ncc(SCC(=O)O)s2)cc1

Standard InChI:  InChI=1S/C21H18N6O4S4/c1-27-11-23-26-21(27)34-15-8-7-14(33-13-5-3-12(31-2)4-6-13)18(24-15)19(30)25-20-22-9-17(35-20)32-10-16(28)29/h3-9,11H,10H2,1-2H3,(H,28,29)(H,22,25,30)

Standard InChI Key:  MJHNYEFAOUYNSZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.1494  -12.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4330  -11.3612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9775  -10.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7676  -10.2187    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170  -10.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7081   -9.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0376   -8.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8500   -8.3729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5547   -7.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741  -16.3575    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
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  1  7  1  0
  7  8  1  0
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  4 13  1  0
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 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
  5 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
  9 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 20 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062363

   ({2-[({3-[(4-methoxyphenyl)sulfanyl]-6-[(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]pyridin-2-yl}carbonyl)amino]-1,3-thiazol-5-yl}sulfanyl)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: 546.68

Molecular Weight (Monoisotopic): 546.0272

AlogP: 4.41

#Rotatable Bonds: 10

Polar Surface Area: 132.12

Molecular Species: ACID

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.05

CX Basic pKa: 1.51

CX LogP: 4.02

CX LogD: 0.71

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -1.83

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