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

ID: ALA5276204

Max Phase: Preclinical

Molecular Formula: C21H19BrN2O4

Molecular Weight: 443.30

Names and Identifiers

Canonical SMILES:  O=C(CNc1ccc(C(=O)/C=C/c2ccccc2Br)cc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C21H19BrN2O4/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:  PFJDBMHSBALKII-HKMNZKMDSA-N

Molfile:  

 
     RDKit          2D

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    1.7096    1.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096    0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    0.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -0.6989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611   -0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -1.5238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901   -0.2864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0007    0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2791   -1.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8084   -1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -1.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2823   -0.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385    0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5692   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2791   -0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2791    0.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    1.7736    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  0
 17 16  1  0
 17 12  1  0
  6 18  2  0
 18 19  1  0
 19  3  2  0
 20  2  1  0
 21 20  2  0
 22 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276204

   ---

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: 443.30

Molecular Weight (Monoisotopic): 442.0528

AlogP: 3.19

#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: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -0.79

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