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

ID: ALA2288775

PubChem CID: 76323902

Max Phase: Preclinical

Molecular Formula: C20H22Cl2N2O5

Molecular Weight: 441.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H22Cl2N2O5/c1-3-4-9-27-18(25)12-23-19(26)13(2)28-15-5-7-16(8-6-15)29-20-17(22)10-14(21)11-24-20/h5-8,10-11,13H,3-4,9,12H2,1-2H3,(H,23,26)

Standard InChI Key:  YXDCKNLSSCDATR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   10.6570  -29.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0542  -30.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8677  -30.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2849  -29.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8827  -28.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0705  -28.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6692  -27.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2666  -30.7613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0838  -30.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5019  -30.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3190  -30.0814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1030  -29.3571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8521  -27.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4553  -27.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6389  -27.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2222  -27.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6278  -28.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4429  -28.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8730  -26.4929    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4050  -27.8830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.7180  -30.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5351  -30.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9341  -31.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4827  -31.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9533  -30.1036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7512  -31.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1501  -32.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9672  -32.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3662  -32.9675    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
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288775

   Butyl 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: 441.31

Molecular Weight (Monoisotopic): 440.0906

AlogP: 4.41

#Rotatable Bonds: 10

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: 11.77

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.40

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