4-Benzyl-1-(4-chloro-2-fluoro-5-iso-propoxycarbonylphenyl)piperazine-2,6-dione

ID: ALA2270107

PubChem CID: 76315932

Max Phase: Preclinical

Molecular Formula: C21H20ClFN2O4

Molecular Weight: 418.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)c1cc(N2C(=O)CN(Cc3ccccc3)CC2=O)c(F)cc1Cl

Standard InChI:  InChI=1S/C21H20ClFN2O4/c1-13(2)29-21(28)15-8-18(17(23)9-16(15)22)25-19(26)11-24(12-20(25)27)10-14-6-4-3-5-7-14/h3-9,13H,10-12H2,1-2H3

Standard InChI Key:  AJEVWTQYVBODSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    6.8155  -28.6869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1655  -28.6869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780  -27.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030  -27.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8155  -30.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8155  -27.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6405  -28.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0530  -27.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8780  -27.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2905  -28.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8780  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0530  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2905  -30.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8780  -30.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1155  -30.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5280  -30.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3530  -30.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1155  -31.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6405  -27.2553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1155  -28.6869    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3405  -28.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9280  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3405  -30.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9280  -30.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1031  -30.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906  -30.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1031  -29.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  2  7  2  0
  6  8  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 15 16  2  0
 18 19  1  0
 18 20  1  0
 17 18  1  0
 15 17  1  0
 13 15  1  0
 10 21  1  0
 12 22  1  0
  1  9  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270107

   Propan-2-yl 5-(4-benzyl-2,6-dioxopiperazin-1-yl)-2-chloro-4-fluorobenzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 418.85

Molecular Weight (Monoisotopic): 418.1096

AlogP: 3.42

#Rotatable Bonds: 5

Polar Surface Area: 66.92

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.46

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -1.25

References

1. Li B, Xiang D, Hsu CT, Liu ZL, Wu C, Yang HZ..  (2005)  A facile synthesis of novel herbicidal 1-phenyl-piperazine-2,6-diones.,  10  (9): [PMID:18007377] [10.3390/10091119]

Source

Source(1):

• Scientific Literature