4-(4-chlorobenzoyl)-5-(4-chlorophenyl)-3-hydroxy-1-(5-(propylthio)-1,3,4-thiadiazol-2-yl)-1H-pyrrol-2(5H)-one

ID: ALA3344319

PubChem CID: 71762786

Max Phase: Preclinical

Molecular Formula: C22H17Cl2N3O3S2

Molecular Weight: 506.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCSc1nnc(N2C(=O)C(O)=C(C(=O)c3ccc(Cl)cc3)C2c2ccc(Cl)cc2)s1

Standard InChI:  InChI=1S/C22H17Cl2N3O3S2/c1-2-11-31-22-26-25-21(32-22)27-17(12-3-7-14(23)8-4-12)16(19(29)20(27)30)18(28)13-5-9-15(24)10-6-13/h3-10,17,29H,2,11H2,1H3

Standard InChI Key:  RNNONJZCEWUIHC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.2348   -4.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0520   -4.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3063   -3.8623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6434   -3.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9846   -3.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0835   -3.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7439   -4.0925    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4057   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1543   -2.8354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3371   -2.8344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5301   -5.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4877   -6.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8203   -5.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3395   -5.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7536   -5.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9410   -5.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0850   -6.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6137   -4.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8019   -4.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3199   -5.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6554   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4662   -5.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2073   -3.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6421   -2.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1826   -3.8666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.7906   -3.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5675   -3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1755   -3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9682   -7.2834    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.5072   -4.9523    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6  7  1  0
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  8  9  2  0
  9 10  1  0
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  2 11  1  0
  1 17  1  0
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 17 19  2  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
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  5 25  1  0
  4 26  2  0
  8 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 31  1  0
 22 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344319

   (4E)-5-(4-chlorophenyl)-4-[(4-chlorophenyl)-hydroxymethylidene]-1-(5-propylsulfanyl-1,3,4-thiadiazol-2-yl)pyrrolidine-2,3-dione

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: 506.44

Molecular Weight (Monoisotopic): 505.0088

AlogP: 6.13

#Rotatable Bonds: 7

Polar Surface Area: 83.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.14

CX Basic pKa: ┄

CX LogP: 5.67

CX LogD: 5.22

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.24

Np Likeness Score: -1.67

References

1. Bhakat S, Karubiu W, Jayaprakash V, Soliman ME..  (2014)  A perspective on targeting non-structural proteins to combat neglected tropical diseases: Dengue, West Nile and Chikungunya viruses.,  87  [PMID:25305334] [10.1016/j.ejmech.2014.10.010]

2. Voss S, Nitsche C..  (2021)  Targeting the protease of West Nile virus.,  12  (8.0): [PMID:34458734] [10.1039/D1MD00080B]

Source

Source(1):

• Scientific Literature