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

ID: ALA5278841

Max Phase: Preclinical

Molecular Formula: C21H18BrFN2O4

Molecular Weight: 461.29

Names and Identifiers

Canonical SMILES:  O=C(CNc1ccc(C(=O)/C=C/c2ccc(Br)cc2F)cc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C21H18BrFN2O4/c22-15-5-1-13(17(23)11-15)4-8-19(26)14-2-6-16(7-3-14)24-12-20(27)25-18-9-10-29-21(18)28/h1-8,11,18,24H,9-10,12H2,(H,25,27)/b8-4+/t18-/m0/s1

Standard InChI Key:  YOAIJIBGXCVXAN-PYJQOMOHSA-N

Molfile:  

 
     RDKit          2D

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    3.4823   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -0.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028   -0.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028    0.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    1.7668    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -0.6976    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7706    0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589    0.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6355    0.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0745   -0.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864   -0.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864    0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    0.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -0.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2098   -0.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215   -0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332   -0.2853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -1.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1457   -1.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6146   -1.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1246   -0.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3373    0.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215   -1.5179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
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  1  9  1  0
  9 10  2  0
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 12 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  1
 23 22  1  0
 23 24  1  0
 24 25  1  0
 26 25  1  0
 22 26  1  0
 26 27  2  0
 20 28  2  0
 11 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278841

   ---

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: 461.29

Molecular Weight (Monoisotopic): 460.0434

AlogP: 3.33

#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: 2.89

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.98

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