1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)-2-chloroethanone

ID: ALA4757878

PubChem CID: 145865973

Max Phase: Preclinical

Molecular Formula: C19H19Cl3N2O

Molecular Weight: 397.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCl)N1CCN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C19H19Cl3N2O/c20-13-18(25)23-9-11-24(12-10-23)19(14-1-5-16(21)6-2-14)15-3-7-17(22)8-4-15/h1-8,19H,9-13H2

Standard InChI Key:  VDANZSQTWKKLOV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   17.6041  -15.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1935  -14.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1935  -16.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6059  -14.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1961  -13.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3699  -13.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9554  -14.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3717  -14.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3692  -16.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9545  -16.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3693  -17.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1988  -17.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6056  -16.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9542  -12.6559    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.9555  -18.3688    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.4293  -15.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8440  -16.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8440  -14.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6693  -14.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0798  -15.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9052  -15.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6693  -16.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3198  -14.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3198  -16.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1451  -16.2292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  2  1  0
  3  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
  6 14  1  0
 11 15  1  0
  1 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 17 22  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 21 23  2  0
 21 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757878

   ---

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: 397.73

Molecular Weight (Monoisotopic): 396.0563

AlogP: 4.47

#Rotatable Bonds: 4

Polar Surface Area: 23.55

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.15

CX LogP: 4.52

CX LogD: 4.52

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.17

References

1. Eaton JK,Furst L,Cai LL,Viswanathan VS,Schreiber SL.  (2020)  Structure-activity relationships of GPX4 inhibitor warheads.,  30  (23.0): [PMID:32920142] [10.1016/j.bmcl.2020.127538]

2. Karaj E, Sindi SH, Kuganesan N, Perera L, Taylor W, Tillekeratne LMV..  (2022)  Tunable Cysteine-Targeting Electrophilic Heteroaromatic Warheads Induce Ferroptosis.,  65  (17.0): [PMID:35984756] [10.1021/acs.jmedchem.2c00909]

Source

Source(1):

• Scientific Literature