2,6-dichlorophenylaminomethylenebisphosphonic acid

ID: ALA2252811

PubChem CID: 24866780

Max Phase: Preclinical

Molecular Formula: C7H9Cl2NO6P2

Molecular Weight: 336.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1c(Cl)cccc1Cl)P(=O)(O)O

Standard InChI:  InChI=1S/C7H9Cl2NO6P2/c8-4-2-1-3-5(9)6(4)10-7(17(11,12)13)18(14,15)16/h1-3,7,10H,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  KGPZOMGTNDRRAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   30.0545   -2.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2373   -2.6579    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.6459   -3.3656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5303   -0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9430   -1.4321    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.3515   -0.7198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4087   -1.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4076   -2.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1156   -3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8253   -2.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8225   -1.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1138   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5286   -1.4382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2379   -1.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6533   -1.8388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1114   -0.6270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.4449   -2.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5336   -3.0796    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14  5  1  0
 14  2  1  0
  5 15  2  0
 12 16  1  0
  2 17  2  0
 10 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252811

   2,6-DICHLOROPHENYLAMINOMETHYLENEBISPHOSPHONIC 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: 336.00

Molecular Weight (Monoisotopic): 334.9282

AlogP: 2.04

#Rotatable Bonds: 4

Polar Surface Area: 127.09

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.95

CX Basic pKa: ┄

CX LogP: 1.19

CX LogD: -3.63

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.53

Np Likeness Score: -0.42

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