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

ID: ALA2289460

PubChem CID: 76320314

Max Phase: Preclinical

Molecular Formula: C15H16FO6PS

Molecular Weight: 374.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccccc1F)c1cccs1

Standard InChI:  InChI=1S/C15H16FO6PS/c1-19-23(18,20-2)15(13-8-5-9-24-13)22-14(17)10-21-12-7-4-3-6-11(12)16/h3-9,15H,10H2,1-2H3

Standard InChI Key:  OLVIIMWWLYPCDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    8.1668  -31.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668  -30.3821    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668  -29.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9840  -30.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3497  -30.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8759  -31.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9600  -32.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7583  -32.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1669  -31.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6191  -31.2735    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4578  -31.6079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7487  -31.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0437  -31.6079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7487  -30.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0437  -29.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3346  -30.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296  -29.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206  -30.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206  -31.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297  -31.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3346  -31.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8759  -29.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3926  -29.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307  -29.1563    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
M  END

Alternative Forms

1. Parent:

   

   ALA2289460

   [Dimethoxyphosphoryl(thiophen-2-yl)methyl] 2-(2-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: 374.33

Molecular Weight (Monoisotopic): 374.0389

AlogP: 3.99

#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: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -1.45

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