2-(2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenoxy)propanamidooxy)acetic acid

ID: ALA2288766

PubChem CID: 76313021

Max Phase: Preclinical

Molecular Formula: C17H15F3N2O6

Molecular Weight: 400.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1)C(=O)NOCC(=O)O

Standard InChI:  InChI=1S/C17H15F3N2O6/c1-10(16(25)22-26-9-15(23)24)27-12-3-5-13(6-4-12)28-14-7-2-11(8-21-14)17(18,19)20/h2-8,10H,9H2,1H3,(H,22,25)(H,23,24)

Standard InChI Key:  KHGMCUUOLBTTGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   17.6980  -17.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0953  -18.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9088  -18.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3259  -17.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9237  -16.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1115  -16.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7103  -16.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3077  -19.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1248  -19.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5238  -19.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5430  -18.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3601  -18.4344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1440  -17.7101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8931  -16.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4964  -15.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6800  -15.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2632  -16.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6689  -16.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4839  -16.9630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7590  -19.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5762  -19.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9751  -19.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7922  -19.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5569  -20.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4461  -16.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0439  -15.5246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0311  -16.9400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6281  -16.2324    0.0000 F   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
  9 11  1  0
 11 12  1  0
 11 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 17 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288766

   2-[2-[4-[5-(Trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoylamino]oxyacetic acid

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: 400.31

Molecular Weight (Monoisotopic): 400.0882

AlogP: 2.79

#Rotatable Bonds: 8

Polar Surface Area: 106.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.15

CX Basic pKa: 0.80

CX LogP: 2.66

CX LogD: -1.70

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.49

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