(E)-4-ethoxy-4-oxobut-2-enyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate

ID: ALA2228654

PubChem CID: 56650112

Max Phase: Preclinical

Molecular Formula: C20H15ClF3NO7

Molecular Weight: 473.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/COC(=O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C20H15ClF3NO7/c1-2-30-18(26)4-3-9-31-19(27)14-11-13(6-7-16(14)25(28)29)32-17-8-5-12(10-15(17)21)20(22,23)24/h3-8,10-11H,2,9H2,1H3/b4-3+

Standard InChI Key:  POOBUTPAWIUQLD-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   17.7993   -2.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7982   -3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5062   -3.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2159   -3.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2131   -2.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5044   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0915   -2.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0913   -1.5437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3839   -2.7697    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2984   -2.1462    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.9192   -2.3545    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.9242   -3.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6313   -3.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3363   -3.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0429   -3.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0421   -2.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3287   -2.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6251   -2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7511   -3.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7519   -4.8101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4583   -3.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1665   -3.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8737   -3.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7528   -2.3526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7504   -1.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4617   -2.7591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5819   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2891   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9973   -3.9883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2883   -2.7633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7046   -3.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4127   -3.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  5 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  2  0
 24 26  1  0
 16 24  1  0
 23 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  1  0
 31 32  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2228654

   [(E)-4-ethoxy-4-oxobut-2-enyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 473.79

Molecular Weight (Monoisotopic): 473.0489

AlogP: 5.34

#Rotatable Bonds: 8

Polar Surface Area: 104.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 5.79

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.22

Np Likeness Score: -0.90

References

1. Yu H, Yang H, Cui D, Lv L, Li B..  (2011)  Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates.,  59  (21): [PMID:21958315] [10.1021/jf2039444]

Source

Source(1):

• Scientific Literature