rac-(2,4-dichlorophenyl)(hydroxy)methylphosphonic acid

ID: ALA2252819

PubChem CID: 24866782

Max Phase: Preclinical

Molecular Formula: C7H7Cl2O4P

Molecular Weight: 257.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C7H7Cl2O4P/c8-4-1-2-5(6(9)3-4)7(10)14(11,12)13/h1-3,7,10H,(H2,11,12,13)

Standard InChI Key:  QMJHGUKCJOPYOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
   29.1356  -10.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7273  -11.2659    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.5522  -11.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8720  -11.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8707  -12.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5856  -12.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3019  -12.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2991  -11.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5838  -10.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0120  -10.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0089  -10.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7310  -12.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5812  -10.0407    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.1560  -12.5176    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
  5 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252819

   (2,4-DICHLOROPHENYL)(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: 257.01

Molecular Weight (Monoisotopic): 255.9459

AlogP: 2.16

#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: 1.31

CX LogD: -1.15

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.71

Np Likeness Score: -0.39

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