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

ID: ALA2289459

PubChem CID: 76309371

Max Phase: Preclinical

Molecular Formula: C16H16F3O6PS

Molecular Weight: 424.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccc(C(F)(F)F)cc1)c1cccs1

Standard InChI:  InChI=1S/C16H16F3O6PS/c1-22-26(21,23-2)15(13-4-3-9-27-13)25-14(20)10-24-12-7-5-11(6-8-12)16(17,18)19/h3-9,15H,10H2,1-2H3

Standard InChI Key:  SORRHFVAGCRBGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.1506  -23.4236    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.1506  -22.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9678  -23.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3334  -23.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8597  -24.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9437  -25.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7421  -25.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1507  -24.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6029  -24.3150    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4415  -24.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7324  -24.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0275  -24.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7324  -23.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0275  -23.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3184  -23.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6134  -23.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9043  -23.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9043  -24.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6134  -24.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3184  -24.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8597  -22.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3764  -22.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1968  -24.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4889  -24.2414    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1971  -25.4669    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4849  -25.0523    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
 19 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289459

   [Dimethoxyphosphoryl(thiophen-2-yl)methyl] 2-[4-(trifluoromethyl)phenoxy]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: 424.33

Molecular Weight (Monoisotopic): 424.0357

AlogP: 4.87

#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: 3.96

CX LogD: 3.96

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -1.24

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