3-(5-isopropoxypyridin-2-yl)-N-(3-methylpyridin-2-yl)-1,2,4-thiadiazol-5-amine

ID: ALA5189355

PubChem CID: 155230579

Max Phase: Preclinical

Molecular Formula: C16H17N5OS

Molecular Weight: 327.41

Names and Identifiers

Canonical SMILES:  Cc1cccnc1Nc1nc(-c2ccc(OC(C)C)cn2)ns1

Standard InChI:  InChI=1S/C16H17N5OS/c1-10(2)22-12-6-7-13(18-9-12)15-20-16(23-21-15)19-14-11(3)5-4-8-17-14/h4-10H,1-3H3,(H,17,19,20,21)

Standard InChI Key:  IYOSZTMOGCTSQK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.1526    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443   -0.3278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1760   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961   -1.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -0.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991    1.0922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799    1.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    0.5692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    0.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386    1.7263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    1.8965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305   -0.3257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594   -0.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450    0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723   -0.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723   -1.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001   -1.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5432   -1.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  8  3  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 14 11  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 14  2  0
 20 17  1  0
 21 20  1  0
 21 22  1  0
 23 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5189355

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 327.41

Molecular Weight (Monoisotopic): 327.1154

AlogP: 3.83

#Rotatable Bonds: 5

Polar Surface Area: 72.82

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.50

CX Basic pKa: 3.18

CX LogP: 4.13

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -1.95

References

1. Hawryluk N, Robinson D, Shen Y, Kyne G, Bedore M, Menon S, Canan S, von Geldern T, Townson S, Gokool S, Ehrens A, Koschel M, Lhermitte-Vallarino N, Martin C, Hoerauf A, Hernandez G, Dalvie D, Specht S, Hübner MP, Scandale I..  (2022)  Discovery of Substituted Di(pyridin-2-yl)-1,2,4-thiadiazol-5-amines as Novel Macrofilaricidal Compounds for the Treatment of Human Filarial Infections.,  65  (16.0): [PMID:35972896] [10.1021/acs.jmedchem.2c00960]

Source

Source(1):

• Scientific Literature