2-(4-(bis(4-chlorophenyl)methyl)piperazine-1-carbonyl)but-2-enenitrile

ID: ALA4758630

PubChem CID: 162656230

Max Phase: Preclinical

Molecular Formula: C22H21Cl2N3O

Molecular Weight: 414.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C(\C#N)C(=O)N1CCN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C22H21Cl2N3O/c1-2-16(15-25)22(28)27-13-11-26(12-14-27)21(17-3-7-19(23)8-4-17)18-5-9-20(24)10-6-18/h2-10,21H,11-14H2,1H3/b16-2+

Standard InChI Key:  DMVGRADEFWHFMB-APQPDGGLSA-N

Molfile:  

 
     RDKit          2D

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    5.0662   -3.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680   -2.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283   -1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4179   -2.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301   -3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8275   -4.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171   -5.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276   -6.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6569   -5.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676   -5.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4168   -1.0025    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -6.7137    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8912   -3.8597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267   -3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5412   -3.8597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3662   -3.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7767   -3.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7767   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3662   -5.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0163   -5.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9554   -6.0070    0.0000 N   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
 24 26  2  0
 26 27  1  0
 25 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4758630

   ---

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: 414.34

Molecular Weight (Monoisotopic): 413.1062

AlogP: 4.70

#Rotatable Bonds: 4

Polar Surface Area: 47.34

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.45

CX LogP: 4.94

CX LogD: 4.93

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.10

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]

Source

Source(1):

• Scientific Literature