O,O'-Dimethyl alpha-(2,4,5-trichlorophenoxyacetoxy)-alpha-(thien-2-yl)-methylphosphonate

ID: ALA2289464

PubChem CID: 71524705

Max Phase: Preclinical

Molecular Formula: C15H14Cl3O6PS

Molecular Weight: 459.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1cc(Cl)c(Cl)cc1Cl)c1cccs1

Standard InChI:  InChI=1S/C15H14Cl3O6PS/c1-21-25(20,22-2)15(13-4-3-5-26-13)24-14(19)8-23-12-7-10(17)9(16)6-11(12)18/h3-7,15H,8H2,1-2H3

Standard InChI Key:  QIDZWBRLXUCDPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.3072  -11.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3072  -10.4806    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3072   -9.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1244  -10.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4900  -10.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0163  -11.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1003  -12.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8987  -12.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3073  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7594  -11.3720    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981  -11.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8890  -11.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1840  -11.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8890  -10.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1840  -10.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4749  -10.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700  -10.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0609  -10.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0609  -11.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700  -11.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4749  -11.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0163   -9.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330   -9.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7710   -9.2548    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3534  -11.7067    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7710  -12.5236    0.0000 Cl  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
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289464

   [Dimethoxyphosphoryl(thiophen-2-yl)methyl] 2-(2,4,5-trichlorophenoxy)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: 459.67

Molecular Weight (Monoisotopic): 457.9314

AlogP: 5.82

#Rotatable Bonds: 8

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: -1.25

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