Diisopropyl 2-(sulfanylmethyl)phenylphosphonate

ID: ALA1173337

PubChem CID: 46173032

Max Phase: Preclinical

Molecular Formula: C13H21O3PS

Molecular Weight: 288.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OP(=O)(OC(C)C)c1ccccc1CS

Standard InChI:  InChI=1S/C13H21O3PS/c1-10(2)15-17(14,16-11(3)4)13-8-6-5-7-12(13)9-18/h5-8,10-11,18H,9H2,1-4H3

Standard InChI Key:  JFZVPWMZPZJUTE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.4590   -0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    0.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555   -0.0983    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    1.1392    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735   -0.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735   -1.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4590   -1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    0.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055   -0.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6680   -0.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    0.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930   -0.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0
  1  5  2  0
  1  9  1  0
  2  3  2  0
 13  3  1  0
 14  3  1  0
 10  4  1  0
  5 10  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 11 15  1  0
 12 16  1  0
 16 13  1  0
 15 14  1  0
 15 17  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1173337

   Bis(1-Methylethyl) [2-(Sulfanylmethyl)phenyl]phosphonate

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: 288.35

Molecular Weight (Monoisotopic): 288.0949

AlogP: 3.78

#Rotatable Bonds: 6

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.92

CX Basic pKa: ┄

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: -0.34

References

1. Lassaux P, Hamel M, Gulea M, Delbrück H, Mercuri PS, Horsfall L, Dehareng D, Kupper M, Frère JM, Hoffmann K, Galleni M, Bebrone C..  (2010)  Mercaptophosphonate compounds as broad-spectrum inhibitors of the metallo-beta-lactamases.,  53  (13): [PMID:20527888] [10.1021/jm100213c]

Source

Source(1):

• Scientific Literature