N-[2-(2-Adamantan-1-yl-acetylamino)-ethyl]-2-[2,3-dichloro-4-(2-methylene-butyryl)-phenoxy]-acetamide

ID: ALA4760889

PubChem CID: 162658747

Max Phase: Preclinical

Molecular Formula: C27H34Cl2N2O4

Molecular Weight: 521.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(CC)C(=O)c1ccc(OCC(=O)NCCNC(=O)CC23CC4CC(CC(C4)C2)C3)c(Cl)c1Cl

Standard InChI:  InChI=1S/C27H34Cl2N2O4/c1-3-16(2)26(34)20-4-5-21(25(29)24(20)28)35-15-23(33)31-7-6-30-22(32)14-27-11-17-8-18(12-27)10-19(9-17)13-27/h4-5,17-19H,2-3,6-15H2,1H3,(H,30,32)(H,31,33)

Standard InChI Key:  VFVKVAKVCDPVQT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   25.5953   -3.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7100   -3.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0497   -3.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6399   -2.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9977   -2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1539   -2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2932   -3.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4635   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0015   -3.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4200   -2.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1093   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8211   -2.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5288   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2407   -2.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5288   -3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9525   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2407   -1.3661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9502   -3.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6612   -3.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3740   -3.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3714   -2.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6598   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0864   -3.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7977   -3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5059   -3.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2172   -3.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5070   -4.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2415   -3.8252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6608   -4.6482    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.9262   -3.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6326   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3416   -3.8164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0480   -3.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7570   -3.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0455   -2.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 18 28  1  0
 19 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34  8  1  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760889

   ---

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: 521.49

Molecular Weight (Monoisotopic): 520.1896

AlogP: 5.36

#Rotatable Bonds: 11

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: -0.39

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