alpha-Sulfanyl(2-methoxybenzyl)phosphonic acid

ID: ALA1173798

Max Phase: Preclinical

Molecular Formula: C8H11O4PS

Molecular Weight: 234.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alpha-Sulfanyl(2-Methoxybenzyl)Phosphonic Acid

Canonical SMILES:  COc1ccccc1C(S)P(=O)(O)O

Standard InChI:  InChI=1S/C8H11O4PS/c1-12-7-5-3-2-4-6(7)8(14)13(9,10)11/h2-5,8,14H,1H3,(H2,9,10,11)

Standard InChI Key:  QXHIPTMANGQMPP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    5.2543   -4.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543   -5.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687   -4.0668    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398   -4.0668    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.8253   -3.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -4.7813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -3.3524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687   -5.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687   -6.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543   -6.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398   -6.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398   -5.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6832   -5.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3977   -5.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  2  8  2  0
  8  9  1  0
  4  5  2  0
  9 10  2  0
  1  3  1  0
 10 11  1  0
  4  6  1  0
 11 12  2  0
 12  2  1  0
  1  2  1  0
  8 13  1  0
  4  7  1  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1173798

   ---

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: 234.21

Molecular Weight (Monoisotopic): 234.0116

AlogP: 1.80

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.50

CX Basic pKa: ┄

CX LogP: 0.88

CX LogD: -1.52

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.55

Np Likeness Score: -0.19

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