rac-(2-chlorophenyl)(hydroxy)methylphosphonic acid

ID: ALA2252816

PubChem CID: 24866947

Max Phase: Preclinical

Molecular Formula: C7H8ClO4P

Molecular Weight: 222.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)c1ccccc1Cl

Standard InChI:  InChI=1S/C7H8ClO4P/c8-6-4-2-1-3-5(6)7(9)13(10,11)12/h1-4,7,9H,(H2,10,11,12)

Standard InChI Key:  LZUSFIFHMFOUOQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    3.8904  -11.8422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823  -12.5586    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068  -12.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275  -12.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263  -13.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410  -13.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572  -13.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543  -12.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392  -12.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670  -12.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639  -11.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4859  -13.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367  -11.3337    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10  2  1  0
 10 11  1  0
  2 12  2  0
  9 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252816

   (2-CHLOROPHENYL)(HYDROXY)METHYLPHOSPHONIC ACID

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: 222.56

Molecular Weight (Monoisotopic): 221.9849

AlogP: 1.51

#Rotatable Bonds: 2

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.22

CX Basic pKa: ┄

CX LogP: 0.74

CX LogD: -1.71

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.66

Np Likeness Score: -0.29

References

1. Forlani G, Occhipinti A, Berlicki L, Dziedzioła G, Wieczorek A, Kafarski P..  (2008)  Tailoring the structure of aminobisphosphonates to target plant P5C reductase.,  56  (9): [PMID:18399639] [10.1021/jf800029t]

2. Occhipinti A, Berlicki Ł, Giberti S, Dziedzioła G, Kafarski P, Forlani G..  (2010)  Effectiveness and mode of action of phosphonate inhibitors of plant glutamine synthetase.,  66  (1): [PMID:19697446] [10.1002/ps.1830]

Source

Source(1):

• Scientific Literature