ethyl 2-(2-(4-(3,5-dichloropyridin-2-yloxy)phenoxy)propanamido)acetate

ID: ALA2288773

PubChem CID: 12942999

Max Phase: Preclinical

Molecular Formula: C18H18Cl2N2O5

Molecular Weight: 413.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CNC(=O)C(C)Oc1ccc(Oc2ncc(Cl)cc2Cl)cc1

Standard InChI:  InChI=1S/C18H18Cl2N2O5/c1-3-25-16(23)10-21-17(24)11(2)26-13-4-6-14(7-5-13)27-18-15(20)8-12(19)9-22-18/h4-9,11H,3,10H2,1-2H3,(H,21,24)

Standard InChI Key:  KZDRZOFIRNIPBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   32.3125  -22.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7098  -23.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5233  -23.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9405  -22.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5382  -22.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7260  -22.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3248  -21.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9222  -24.2981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7393  -24.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1575  -23.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9746  -23.6182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7586  -22.8939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5077  -21.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1109  -20.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2945  -20.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8778  -21.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2834  -22.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0984  -22.1468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5286  -20.0296    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.0606  -21.4198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.3736  -24.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1907  -24.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5896  -25.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1383  -25.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6089  -23.6404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4067  -25.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8057  -25.7800    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
  6  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  7 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
 14 19  1  0
 16 20  1  0
 11 21  1  0
 21 22  1  0
 22 23  1  0
  9 24  1  0
 22 25  2  0
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288773

   Ethyl 2-[2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoylamino]acetate

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: 413.26

Molecular Weight (Monoisotopic): 412.0593

AlogP: 3.63

#Rotatable Bonds: 8

Polar Surface Area: 86.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.57

References

1. MATSUMOTO K, IDE K, HAYASE Y, TAKAHASHI T, TAKEDA R, HAYASHI Y.  (1996)  Selective Herbicidal Activity of 3, 5-Dichloropyridyloxy-phenoxypropionamidoxyacetic Acid Derivatives between Wheat and Wild Oat,  21  (2): [10.1584/jpestics.21.165]

Source

Source(1):

• Scientific Literature