(dimethoxyphosphoryl)(thiophen-2-yl)methyl 2-(2-chloro-4-fluorophenoxy)acetate

ID: ALA2289463

PubChem CID: 76313082

Max Phase: Preclinical

Molecular Formula: C15H15ClFO6PS

Molecular Weight: 408.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccc(F)cc1Cl)c1cccs1

Standard InChI:  InChI=1S/C15H15ClFO6PS/c1-20-24(19,21-2)15(13-4-3-7-25-13)23-14(18)9-22-12-6-5-10(17)8-11(12)16/h3-8,15H,9H2,1-2H3

Standard InChI Key:  VBHFVDVBMSXXIQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   17.3087   -4.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3087   -3.4850    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.3087   -2.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1258   -3.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4915   -3.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0177   -4.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1018   -5.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9002   -5.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3088   -4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7609   -4.3764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5996   -4.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8905   -4.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1855   -4.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8905   -3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1855   -3.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4764   -3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7715   -3.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0624   -3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0624   -4.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7715   -4.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4764   -4.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0177   -2.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5344   -2.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7725   -2.2592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3548   -4.7111    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:

   

   ALA2289463

   [Dimethoxyphosphoryl(thiophen-2-yl)methyl] 2-(2-chloro-4-fluorophenoxy)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: 408.77

Molecular Weight (Monoisotopic): 408.0000

AlogP: 4.65

#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: 3.80

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: -1.60

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