MMV1497179

ID: ALA3733954

PubChem CID: 2797663

Max Phase: Preclinical

Molecular Formula: C18H17ClN2S

Molecular Weight: 328.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-n2c(-c3ccc(Cl)c(C)c3)csc2=N)c(C)c1

Standard InChI:  InChI=1S/C18H17ClN2S/c1-11-4-7-16(13(3)8-11)21-17(10-22-18(21)20)14-5-6-15(19)12(2)9-14/h4-10,20H,1-3H3

Standard InChI Key:  DEMLCABAAGGTEY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.2424    6.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    7.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    7.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896    8.8582    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859    9.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844    9.3628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   11.4401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   10.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   11.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825   12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   11.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   10.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    9.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4806   12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689    7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    6.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4718    4.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0452    4.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305    5.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5865    3.8562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    2.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  5  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
  1 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  1  1  0
 17 20  1  0
 18 21  1  0
  9 22  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA3733954

   4-(4-Chloro-3-methylphenyl)-3-(2,4-dimethylphenyl)-1,3-thiazol-2-imine;hydrochloride

2. Parent:

   

   ALA3733954

   4-(4-Chloro-3-methylphenyl)-3-(2,4-dimethylphenyl)-1,3-thiazol-2-imine

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: 328.87

Molecular Weight (Monoisotopic): 328.0801

AlogP: 5.26

#Rotatable Bonds: 2

Polar Surface Area: 28.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.82

CX LogP: 5.86

CX LogD: 5.30

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -1.48

References

1. 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(1):

• Winzeler Lab Plasmodium Screening Data