6-((7-Nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexyl-4-oxo-4-(o-tolylamino)butanoate

ID: ALA4757338

PubChem CID: 162657201

Max Phase: Preclinical

Molecular Formula: C23H26N4O6S

Molecular Weight: 486.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccccc1NC(=O)CCC(=O)OCCCCCCSc1ccc([N+](=O)[O-])c2nonc12

Standard InChI:  InChI=1S/C23H26N4O6S/c1-16-8-4-5-9-17(16)24-20(28)12-13-21(29)32-14-6-2-3-7-15-34-19-11-10-18(27(30)31)22-23(19)26-33-25-22/h4-5,8-11H,2-3,6-7,12-15H2,1H3,(H,24,28)

Standard InChI Key:  WUJVTMVDVOILKL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    1.5091  -11.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080  -11.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2160  -12.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143  -10.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229  -11.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277  -11.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121  -12.1551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1921  -11.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7043  -10.8232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -9.8596    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -9.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272   -9.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3337   -9.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -9.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491   -9.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4581   -9.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1645   -9.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9954   -9.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7043   -9.8343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9929   -8.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8759  -10.6599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4108   -9.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2138  -13.1343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057  -13.5421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211  -13.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1188   -9.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8248   -9.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8228   -8.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1089   -8.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4058   -8.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1202  -10.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9  5  2  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18 24  2  0
 22 25  1  0
 26 27  1  0
 26 28  2  0
  3 26  1  0
 25 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 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:

   

   ALA4757338

   ---

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: 486.55

Molecular Weight (Monoisotopic): 486.1573

AlogP: 5.05

#Rotatable Bonds: 13

Polar Surface Area: 137.46

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -1.51

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