2,5-dichlorophenylaminomethylenebisphosphonic acid

ID: ALA2252810

PubChem CID: 24866944

Max Phase: Preclinical

Molecular Formula: C7H9Cl2NO6P2

Molecular Weight: 336.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1cc(Cl)ccc1Cl)P(=O)(O)O

Standard InChI:  InChI=1S/C7H9Cl2NO6P2/c8-4-1-2-5(9)6(3-4)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:  VLVPKMQLPUGWRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   23.8306   -2.6538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0134   -2.6538    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.4220   -3.3615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3065   -0.7181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7192   -1.4280    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.1276   -0.7157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1849   -1.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1837   -2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8918   -3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6014   -2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5986   -1.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8900   -1.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3048   -1.4341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0140   -1.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3109   -3.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4294   -1.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8875   -0.6229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.8916   -3.8947    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
  2 15  2  0
  5 16  2  0
 12 17  1  0
  9 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252810

   2,5-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: -0.85

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