tert-butyl 6-(2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetamido)hexylcarbamate

ID: ALA4783350

PubChem CID: 162665976

Max Phase: Preclinical

Molecular Formula: C24H34Cl2N2O5

Molecular Weight: 501.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(CC)C(=O)c1ccc(OCC(=O)NCCCCCCNC(=O)OC(C)(C)C)c(Cl)c1Cl

Standard InChI:  InChI=1S/C24H34Cl2N2O5/c1-6-16(2)22(30)17-11-12-18(21(26)20(17)25)32-15-19(29)27-13-9-7-8-10-14-28-23(31)33-24(3,4)5/h11-12H,2,6-10,13-15H2,1,3-5H3,(H,27,29)(H,28,31)

Standard InChI Key:  BLNSJDGPVIVNCE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
   18.6950  -11.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6977  -12.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8360  -12.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1194  -12.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5321  -11.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7065  -11.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4098  -12.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9880  -12.9898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318  -13.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0084  -12.5887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7198  -11.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5786  -11.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2895  -11.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4314  -13.8271    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0046  -11.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5782  -12.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2938  -13.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4304  -12.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4304  -11.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0046  -10.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1453  -11.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7207  -12.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1479  -12.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175  -12.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8637  -13.0045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054  -12.9997    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2895  -12.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2949  -13.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8594  -11.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1424  -12.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8532  -12.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5652  -12.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2760  -12.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0
  2  7  1  0
  4  3  1  0
  2  1  2  0
  8  2  1  0
  4  6  1  0
  5  4  1  0
 15 11  1  0
 13 27  2  0
 24 26  1  0
 17 10  1  0
 23 25  1  0
 21 19  2  0
  9 23  2  0
 11 24  2  0
 23 21  1  0
 19 11  1  0
 12 13  1  0
 24  9  1  0
  9 14  1  0
 13 15  1  0
 15 20  2  0
 29 12  1  0
 22 18  1  0
 25 16  1  0
 10 22  1  0
 16 17  1  0
 17 28  2  0
 18 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4783350

   ---

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: 501.45

Molecular Weight (Monoisotopic): 500.1845

AlogP: 5.72

#Rotatable Bonds: 13

Polar Surface Area: 93.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.23

CX LogD: 5.23

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: -0.47

References

1. Li X,Lü Z,Wang C,Li K,Xu F,Xu P,Niu Y.  (2021)  Induction of Apoptosis in Cancer Cells by Glutathione Transferase Inhibitor Mediated Hydrophobic Tagging Molecules.,  12  (5.0): [PMID:34055217] [10.1021/acsmedchemlett.0c00627]

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