3,4-dichlorophenylaminomethylenebisphosphonic acid

ID: ALA2440433

PubChem CID: 24866945

Max Phase: Preclinical

Molecular Formula: C7H9Cl2NO6P2

Molecular Weight: 336.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1ccc(Cl)c(Cl)c1)P(=O)(O)O

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

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    5.4144  -21.6714    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.8257  -22.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2316  -21.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175  -20.4429    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288  -21.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9347  -20.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5822  -20.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5811  -21.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891  -22.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988  -21.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960  -20.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873  -20.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7021  -20.4482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4114  -20.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083  -22.0826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1145  -19.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731  -22.0907    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8744  -20.4547    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  4  1  0
  4  6  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  4  1  0
 14  1  1  0
  1 15  2  0
  4 16  2  0
  8 17  1  0
  7 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2440433

   3,4-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: -0.83

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]

3. Tauro M, Laghezza A, Loiodice F, Agamennone M, Campestre C, Tortorella P..  (2013)  Arylamino methylene bisphosphonate derivatives as bone seeking matrix metalloproteinase inhibitors.,  21  (21): [PMID:24071448] [10.1016/j.bmc.2013.08.054]

4. Tauro M, Loiodice F, Ceruso M, Supuran CT, Tortorella P..  (2014)  Arylamino bisphosphonates: potent and selective inhibitors of the tumor-associated carbonic anhydrase XII.,  24  (8): [PMID:24650641] [10.1016/j.bmcl.2014.03.001]

Source

Source(1):

• Scientific Literature