O,O-Dimethyl alpha-(2-methyl-4-chlorophenoxyacetoxy)-3-nitrobenzylphosphonate

ID: ALA2227944

PubChem CID: 53242609

Max Phase: Preclinical

Molecular Formula: C18H19ClNO8P

Molecular Weight: 443.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(OC)C(OC(=O)COc1ccc(Cl)cc1C)c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H19ClNO8P/c1-12-9-14(19)7-8-16(12)27-11-17(21)28-18(29(24,25-2)26-3)13-5-4-6-15(10-13)20(22)23/h4-10,18H,11H2,1-3H3

Standard InChI Key:  RDNNVCGYIMNCMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.0576  -29.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2422  -29.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353  -30.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2427  -30.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0612  -30.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4644  -30.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181  -30.1577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093  -30.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921  -30.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834  -31.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837  -30.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665  -30.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581  -29.4493    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409  -29.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5669  -28.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464  -30.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570  -30.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325  -28.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591  -30.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408  -30.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9321  -31.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406  -32.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1620  -32.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670  -31.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748  -32.9836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3920  -32.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1686  -33.6926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8342  -28.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2816  -30.1537    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 13 16  1  0
 16 17  1  0
 14 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 12 19  1  0
 25 26  2  0
 25 27  1  0
 23 25  1  0
  2 28  1  0
  6 29  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2227944

   [Dimethoxyphosphoryl-(3-nitrophenyl)methyl] 2-(4-chloro-2-methylphenoxy)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: 443.78

Molecular Weight (Monoisotopic): 443.0537

AlogP: 4.66

#Rotatable Bonds: 9

Polar Surface Area: 114.20

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: -1.17

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