rac-(4-chlorophenyl)(hydroxy)methylphosphonic acid

ID: ALA2252820

PubChem CID: 18702410

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)c1ccc(Cl)cc1

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

Standard InChI Key:  HPPXSNUAVNMIES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   35.3047  -10.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8964  -10.9754    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   35.7210  -10.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0419  -10.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0407  -11.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7553  -12.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4714  -11.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4686  -10.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7535  -10.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1812  -10.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1782   -9.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9002  -11.8035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3262  -12.2268    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
  5 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252820

   (4-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: -0.06

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