6-((7-Nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexyl-4-((2-chlorophenyl)amino)-4-oxo-butan-oate

ID: ALA4762005

PubChem CID: 162659214

Max Phase: Preclinical

Molecular Formula: C22H23ClN4O6S

Molecular Weight: 506.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCC(=O)OCCCCCCSc1ccc([N+](=O)[O-])c2nonc12)Nc1ccccc1Cl

Standard InChI:  InChI=1S/C22H23ClN4O6S/c23-15-7-3-4-8-16(15)24-19(28)11-12-20(29)32-13-5-1-2-6-14-34-18-10-9-17(27(30)31)21-22(18)26-33-25-21/h3-4,7-10H,1-2,5-6,11-14H2,(H,24,28)

Standard InChI Key:  ZHYMGFQECXGQIJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.5685   -3.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5673   -4.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2754   -4.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2736   -2.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9822   -3.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.2711   -1.9643    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.9776   -1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.3930   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1020   -1.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.2239   -1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.7636   -1.9389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0522   -0.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9352   -2.7645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4701   -1.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2731   -5.2389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5650   -5.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9804   -5.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1817   -1.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8877   -1.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8857   -0.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1718   -0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4687   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1831   -2.7554    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
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  3 26  1  0
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 32 33  2  0
 33 25  1  0
 29 34  1  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4762005

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 506.97

Molecular Weight (Monoisotopic): 506.1027

AlogP: 5.40

#Rotatable Bonds: 13

Polar Surface Area: 137.46

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 4.87

CX LogD: 4.87

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.11

Np Likeness Score: -1.57

References

1. Liu Q,Liu Z,Hua W,Gou S.  (2021)  Discovery of 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol Derivatives as Glutathione Transferase Inhibitors with Favorable Selectivity and Tolerated Toxicity.,  64  (3.0): [PMID:33529017] [10.1021/acs.jmedchem.0c02048]

2. Yang, Xinmei X and 10 more authors.  2010-02-11  Novel oxadiazole analogues derived from ethacrynic acid: design, synthesis, and structure-activity relationships in inhibiting the activity of glutathione S-transferase P1-1 and cancer cell proliferation.  [PMID:20055416]

Source

Source(1):

• Scientific Literature