1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)prop-2-yn-1-one

ID: ALA4779501

PubChem CID: 162663256

Max Phase: Preclinical

Molecular Formula: C20H18Cl2N2O

Molecular Weight: 373.28

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18Cl2N2O/c1-2-19(25)23-11-13-24(14-12-23)20(15-3-7-17(21)8-4-15)16-5-9-18(22)10-6-16/h1,3-10,20H,11-14H2

Standard InChI Key:  LGFAIWUEBNWVDP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   29.1371  -15.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7264  -14.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7264  -16.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1389  -13.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7289  -13.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9026  -13.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4879  -13.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9044  -14.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9018  -16.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4871  -16.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9020  -17.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7317  -17.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1385  -16.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4868  -12.5351    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.4881  -18.2496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.9626  -15.3940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3774  -16.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3774  -14.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2029  -14.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6135  -15.3940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4390  -15.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2029  -16.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8539  -14.6786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8539  -16.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2664  -16.8238    0.0000 C   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  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4779501

   ---

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: 373.28

Molecular Weight (Monoisotopic): 372.0796

AlogP: 3.86

#Rotatable Bonds: 3

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: 5.38

CX LogP: 4.39

CX LogD: 4.38

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.97

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