2-(2-(4-chlorophenyl)-2-oxoethylthio)-6-(dimethoxymethyl)nicotinonitrile

ID: ALA1673327

PubChem CID: 2745234

Max Phase: Preclinical

Molecular Formula: C17H15ClN2O3S

Molecular Weight: 362.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(OC)c1ccc(C#N)c(SCC(=O)c2ccc(Cl)cc2)n1

Standard InChI:  InChI=1S/C17H15ClN2O3S/c1-22-17(23-2)14-8-5-12(9-19)16(20-14)24-10-15(21)11-3-6-13(18)7-4-11/h3-8,17H,10H2,1-2H3

Standard InChI Key:  AASHFFLMTFAAAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.1277  -11.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266  -12.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414  -12.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578  -12.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550  -11.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396  -11.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4132  -11.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130  -10.4043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -9.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6988  -11.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990  -12.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679  -11.2228    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9839  -11.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6968  -11.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4128  -11.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6937  -10.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4128  -12.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1280  -12.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419  -12.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8361  -11.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204  -11.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5585  -12.8544    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2713  -12.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865  -13.2894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  1  0
  1  7  1  0
 14 15  1  0
  3  4  2  0
 14 16  2  0
  7  8  1  0
 15 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  7 10  1  0
 20 21  2  0
 21 15  1  0
  2  3  1  0
 19 22  1  0
 10 11  1  0
  5  6  2  0
 23 24  3  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1673327

   2-(2-(4-Chlorophenyl)-2-oxoethylthio)-6-(dimethoxymethyl)nicotinonitrile

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: 362.84

Molecular Weight (Monoisotopic): 362.0492

AlogP: 3.87

#Rotatable Bonds: 7

Polar Surface Area: 72.21

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.65

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.42

Np Likeness Score: -1.54

References

1. King-Keller S, Li M, Smith A, Zheng S, Kaur G, Yang X, Wang B, Docampo R..  (2010)  Chemical validation of phosphodiesterase C as a chemotherapeutic target in Trypanosoma cruzi, the etiological agent of Chagas' disease.,  54  (9): [PMID:20625148] [10.1128/aac.00313-10]

2. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data