(E)-1-ethoxy-1-oxohex-2-en-3-yl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate

ID: ALA2228785

PubChem CID: 56654889

Max Phase: Preclinical

Molecular Formula: C22H19ClF3NO7

Molecular Weight: 501.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC/C(=C\C(=O)OCC)OC(=O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C22H19ClF3NO7/c1-3-5-14(12-20(28)32-4-2)34-21(29)16-11-15(7-8-18(16)27(30)31)33-19-9-6-13(10-17(19)23)22(24,25)26/h6-12H,3-5H2,1-2H3/b14-12+

Standard InChI Key:  CBJFZNHXNLLGJY-WYMLVPIESA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   30.0366  -13.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0354  -14.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7435  -14.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4531  -14.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4503  -13.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7417  -12.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3287  -12.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3285  -11.9691    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.6211  -13.1951    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.5357  -12.5715    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.1564  -12.7799    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.1615  -14.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8685  -14.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5735  -14.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2801  -14.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2793  -13.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5660  -12.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8623  -13.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9883  -14.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9892  -15.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6955  -14.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4037  -14.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1110  -14.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4046  -15.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8191  -14.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5264  -14.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8200  -15.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2345  -14.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9900  -12.7779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9876  -11.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6989  -13.1845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6973  -15.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6982  -16.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2354  -15.2309    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  2  0
 22 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 29 30  2  0
 29 31  1  0
 16 29  1  0
 24 32  1  0
 32 33  1  0
 28 34  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2228785

   [(E)-1-ethoxy-1-oxohex-2-en-3-yl] 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: 501.84

Molecular Weight (Monoisotopic): 501.0802

AlogP: 6.46

#Rotatable Bonds: 9

Polar Surface Area: 104.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.61

CX LogD: 6.61

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.13

Np Likeness Score: -0.81

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