(S,E)-2-(4-(3-(3-nitrophenyl)acryloyl)phenoxy)-N-(2-oxotetrahydrofuran-3-yl)acetamide

ID: ALA4520055

PubChem CID: 155542147

Max Phase: Preclinical

Molecular Formula: C21H18N2O7

Molecular Weight: 410.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc(C(=O)/C=C/c2cccc([N+](=O)[O-])c2)cc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C21H18N2O7/c24-19(9-4-14-2-1-3-16(12-14)23(27)28)15-5-7-17(8-6-15)30-13-20(25)22-18-10-11-29-21(18)26/h1-9,12,18H,10-11,13H2,(H,22,25)/b9-4+/t18-/m0/s1

Standard InChI Key:  SQSFMLVFUDDONF-URPWPPKMSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.9908  -24.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8080  -24.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624  -23.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994  -23.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407  -23.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701  -23.1744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982  -22.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778  -23.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855  -23.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778  -24.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932  -23.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6009  -23.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074  -23.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0147  -23.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0151  -22.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3024  -21.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5981  -22.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223  -21.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4305  -22.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7212  -21.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1377  -21.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8459  -22.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8447  -23.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521  -23.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2603  -23.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565  -22.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5485  -21.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9622  -21.9400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6719  -22.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9583  -21.1228    0.0000 O   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  1  1  0
  3  6  1  1
  4  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4520055

   ---

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: 410.38

Molecular Weight (Monoisotopic): 410.1114

AlogP: 2.30

#Rotatable Bonds: 8

Polar Surface Area: 124.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.49

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.23

Np Likeness Score: -0.88

References

1. Yu B, Liu H, Kong X, Chen X, Wu C..  (2019)  Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation.,  163  [PMID:30553142] [10.1016/j.ejmech.2018.12.014]

Source

Source(1):

• Scientific Literature