Rac-N-(1-(4-(benzyloxy)phenyl)-4-(2,4-dichlorophenyl)azetidin-2-ylidene)-4-iodoaniline

ID: ALA4864325

PubChem CID: 164624515

Max Phase: Preclinical

Molecular Formula: C28H21Cl2IN2O

Molecular Weight: 599.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Clc1ccc(C2C/C(=N\c3ccc(I)cc3)N2c2ccc(OCc3ccccc3)cc2)c(Cl)c1

Standard InChI:  InChI=1S/C28H21Cl2IN2O/c29-20-6-15-25(26(30)16-20)27-17-28(32-22-9-7-21(31)8-10-22)33(27)23-11-13-24(14-12-23)34-18-19-4-2-1-3-5-19/h1-16,27H,17-18H2/b32-28+

Standard InChI Key:  PWXMMKROOCQOOS-VEWQFJOQSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   34.3570   -3.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3570   -4.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1839   -4.7579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1839   -3.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7685   -5.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5540   -6.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1350   -6.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9348   -6.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1464   -5.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5638   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7656   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5652   -3.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1467   -2.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5521   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7711   -5.3439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9722   -5.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7614   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9633   -4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3764   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5972   -5.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3948   -5.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   -7.0971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3202   -6.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1303   -1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9298   -2.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5810   -4.4921    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   38.9020   -7.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6876   -8.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2686   -8.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0643   -8.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2758   -7.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6932   -7.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5103   -1.5980    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.7564   -2.3449    0.0000 Cl  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  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3  5  1  0
 11 12  2  0
 12 13  1  0
 13 25  2  0
 24 14  2  0
 14 11  1  0
  4 11  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 22  1  0
 22 23  1  0
 24 25  1  0
 19 26  1  0
 23 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 25 33  1  0
 14 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4864325

   ---

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: 599.30

Molecular Weight (Monoisotopic): 598.0076

AlogP: 8.86

#Rotatable Bonds: 6

Polar Surface Area: 24.83

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 6.76

CX LogP: 8.87

CX LogD: 8.78

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: -1.10

References

1. Romero E, Oueslati S, Benchekroun M, D'Hollander ACA, Ventre S, Vijayakumar K, Minard C, Exilie C, Tlili L, Retailleau P, Zavala A, Elisée E, Selwa E, Nguyen LA, Pruvost A, Naas T, Iorga BI, Dodd RH, Cariou K..  (2021)  Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D).,  219  [PMID:33862516] [10.1016/j.ejmech.2021.113418]

Source

Source(1):

• Scientific Literature