(dimethoxyphosphoryl)(phenyl)methyl 2-(2,4-dichlorophenoxy)acetate

ID: ALA2227682

PubChem CID: 12099425

Max Phase: Preclinical

Molecular Formula: C17H17Cl2O6P

Molecular Weight: 419.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccc(Cl)cc1Cl)c1ccccc1

Standard InChI:  InChI=1S/C17H17Cl2O6P/c1-22-26(21,23-2)17(12-6-4-3-5-7-12)25-16(20)11-24-15-9-8-13(18)10-14(15)19/h3-10,17H,11H2,1-2H3

Standard InChI Key:  WQIOJXADIUGZPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   25.4454  -16.0819    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.2228  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4073  -15.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0004  -16.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4078  -16.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2263  -16.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6296  -16.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1832  -16.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7745  -16.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9573  -16.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5485  -17.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5489  -16.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7317  -16.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3232  -15.3755    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.5061  -15.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7320  -14.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1115  -16.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3222  -16.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0976  -14.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3243  -16.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5060  -16.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0973  -17.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5058  -18.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3272  -18.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7322  -17.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9993  -14.6716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 15 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 13 20  1  0
  7  1  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2227682

   [Dimethoxyphosphoryl(phenyl)methyl] 2-(2,4-dichlorophenoxy)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: 419.20

Molecular Weight (Monoisotopic): 418.0140

AlogP: 5.10

#Rotatable Bonds: 8

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.79

References

1. He HW, Yuan JL, Peng H, Chen T, Shen P, Wan SQ, Li Y, Tan HL, He YH, He JB, Li Y..  (2011)  Studies of O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex.,  59  (9): [PMID:21452831] [10.1021/jf104247w]

Source

Source(1):

• Scientific Literature