O,O'-Dimethyl alpha-(2,4-difluorophenoxyacetoxy)-alpha-(thien-2-yl)-methylphosphonate

ID: ALA2289461

PubChem CID: 71524651

Max Phase: Preclinical

Molecular Formula: C15H15F2O6PS

Molecular Weight: 392.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccc(F)cc1F)c1cccs1

Standard InChI:  InChI=1S/C15H15F2O6PS/c1-20-24(19,21-2)15(13-4-3-7-25-13)23-14(18)9-22-12-6-5-10(16)8-11(12)17/h3-8,15H,9H2,1-2H3

Standard InChI Key:  ANEIYFWLGDTPGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.6252  -31.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6252  -30.2294    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.6252  -29.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4424  -30.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8080  -30.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3343  -31.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4184  -32.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2167  -32.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6253  -31.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0775  -31.1208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9162  -31.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2071  -31.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5021  -31.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2071  -30.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5021  -29.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7930  -30.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0880  -29.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3790  -30.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3790  -31.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0880  -31.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7930  -31.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3343  -29.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8510  -29.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0891  -29.0036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6714  -31.4555    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  5  2  0
  1  2  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  6 10  1  0
  1  6  1  0
 12 13  2  0
 12 14  1  0
 11 12  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 15 16  1  0
 14 15  1  0
  1 11  1  0
  3 22  1  0
  4 23  1  0
 17 24  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289461

   [Dimethoxyphosphoryl(thiophen-2-yl)methyl] 2-(2,4-difluorophenoxy)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: 392.32

Molecular Weight (Monoisotopic): 392.0295

AlogP: 4.13

#Rotatable Bonds: 8

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -1.54

References

1. He HW, Peng H, Wang T, Wang C, Yuan JL, Chen T, He J, Tan X..  (2013)  α-(Substituted-phenoxyacetoxy)-α-heterocyclylmethylphosphonates: synthesis, herbicidal activity, inhibition on pyruvate dehydrogenase complex (PDHc), and application as postemergent herbicide against broadleaf weeds.,  61  (10): [PMID:23398199] [10.1021/jf305153h]

Source

Source(1):

• Scientific Literature