(S,E)-2-((4-(3-(2-chlorophenyl)acryloyl)phenyl)amino)-N-(2-oxotetrahydrofuran-3-yl)acetamide

ID: ALA5283130

Max Phase: Preclinical

Molecular Formula: C21H19ClN2O4

Molecular Weight: 398.85

Names and Identifiers

Canonical SMILES:  O=C(CNc1ccc(C(=O)/C=C/c2ccccc2Cl)cc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C21H19ClN2O4/c22-17-4-2-1-3-14(17)7-10-19(25)15-5-8-16(9-6-15)23-13-20(26)24-18-11-12-28-21(18)27/h1-10,18,23H,11-13H2,(H,24,26)/b10-7+/t18-/m0/s1

Standard InChI Key:  RWALYVZWJRSMCV-HKMNZKMDSA-N

Molfile:  

 
     RDKit          2D

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    1.7098    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    0.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    0.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322   -0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -0.6989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758   -0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758   -1.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2903   -0.2864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048   -0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7876   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2795   -1.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088   -1.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048   -1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2823   -0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953   -0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4243    0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2795   -0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2795    0.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5678    0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5678    1.7738    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
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  6 18  2  0
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 26 27  1  0
 27 22  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283130

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.85

Molecular Weight (Monoisotopic): 398.1033

AlogP: 3.08

#Rotatable Bonds: 7

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.90

CX Basic pKa: 1.35

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.96

References

1. Ampomah-Wireko M, Luo C, Cao Y, Wang H, Nininahazwe L, Wu C..  (2021)  Chemical probe of AHL modulators on quorum sensing in Gram-Negative Bacteria and as antiproliferative agents: A review.,  226  [PMID:34626877] [10.1016/j.ejmech.2021.113864]

Source

Source(1):

• Scientific Literature