[(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid

ID: ALA539675

PubChem CID: 24866948

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)c1cccc(Cl)c1

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

Standard InChI Key:  HICJUVHIXUVWHA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    2.4167   -2.3917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -3.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -1.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -1.9917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  3  2  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  5  1  0
 10  9  1  0
 11  3  1  0
 12 11  2  0
 13 12  1  0
  9 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA539675

   (3-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: -0.17

References

1. Frechette RF, Ackerman C, Beers S, Look R, Moore J.  (1997)  Novel hydroxyphosphonate inhibitors of CD-45 tyrosine phosphatase,  7  (17): [10.1016/S0960-894X(97)00390-9]

2. 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]

3. 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