(R)-butyl 2-(4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy)propanoate

ID: ALA2286495

PubChem CID: 76316397

Max Phase: Preclinical

Molecular Formula: C18H19ClFNO4

Molecular Weight: 367.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC(=O)[C@@H](C)Oc1ccc(Oc2ncc(Cl)cc2F)cc1

Standard InChI:  InChI=1S/C18H19ClFNO4/c1-3-4-9-23-18(22)12(2)24-14-5-7-15(8-6-14)25-17-16(20)10-13(19)11-21-17/h5-8,10-12H,3-4,9H2,1-2H3/t12-/m1/s1

Standard InChI Key:  WAHCDVGKSSIALI-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

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    9.9026  -29.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9038  -28.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1957  -28.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4861  -28.8351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4889  -29.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1975  -30.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6118  -28.4266    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2000  -30.8802    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7827  -30.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0735  -29.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0738  -28.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3653  -28.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582  -28.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639  -29.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729  -30.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484  -28.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2428  -28.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330  -28.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2470  -29.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414  -30.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567  -30.0831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316  -29.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1260  -30.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162  -29.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120  -28.8754    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
  2  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286495

   butyl (2R)-2-[4-(5-chloro-3-fluoropyridin-2-yl)oxyphenoxy]propanoate

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: 367.80

Molecular Weight (Monoisotopic): 367.0987

AlogP: 4.78

#Rotatable Bonds: 8

Polar Surface Area: 57.65

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.96

CX LogD: 4.96

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -1.34

References

1. Tajik H, Dadras A, Aghabeygi S.  (2011)  A facile synthesis of novel optically active R,R-2-(4-(2-(4-(5-chloro-3-halo-pyridin-2-yloxy)-phenoxy)-propionyloxy)-phenoxy)-propionic acid esters using cyanuric chloride as potential herbicide,  22  (5): [10.1016/j.cclet.2010.12.001]

Source

Source(1):

• Scientific Literature