[(3,5-Dichloro-phenylamino)-phosphono-methyl]-phosphonic acid

ID: ALA55518

Cas Number: 195000-01-2

PubChem CID: 405402

Max Phase: Preclinical

Molecular Formula: C7H9Cl2NO6P2

Molecular Weight: 336.00

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (3,5-Dichlorophenylamino)Methylenediphosphonic Acid | {[(3,5-dichlorophenyl)amino]methanediyl}bis(phosphonic acid)|195000-01-2|(3,5-Dichlorophenylamino)Methylenediphosphonic Acid|{[(3,5-dichlorophenyl)amino]methylene}bis(phosphonic acid)|NSC722628|[[(3,1-bisphosphonate|CHEMBL55518|DTXSID20328071|BDBM50487061|NSC-722628|BWJ

Canonical SMILES:  O=P(O)(O)C(Nc1cc(Cl)cc(Cl)c1)P(=O)(O)O

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

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.7417   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.6917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -0.2667    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -1.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -1.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667    0.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    0.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625   -2.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -2.6667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -3.9167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  2  2  0
  7  3  2  0
  8  5  2  0
  9  5  1  0
 10  9  2  0
 11  8  1  0
 12 10  1  0
 13  3  1  0
 14  3  1  0
 15  2  1  0
 16  2  1  0
 17 11  1  0
 18 10  1  0
 11 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA55518

   (3,5-DICHLOROPHENYLAMINO)METHYLENEDIPHOSPHONIC 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: -0.56

References

1. Ghosh S, Chan JM, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E..  (2004)  Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.,  47  (1): [PMID:14695831] [10.1021/jm030084x]

2. Leon A, Liu L, Yang Y, Hudock MP, Hall P, Yin F, Studer D, Puan KJ, Morita CT, Oldfield E..  (2006)  Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.,  49  (25): [PMID:17149863] [10.1021/jm060492b]

3. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

4. Forlani G, Giberti S, Berlicki L, Petrollino D, Kafarski P..  (2007)  Plant P5C reductase as a new target for aminomethylenebisphosphonates.,  55  (11): [PMID:17474756] [10.1021/jf0701032]

5. 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]

6. 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]

7. Obojska A, Berlicki L, Kafarski P, Lejczak B, Chicca M, Forlani G..  (2004)  Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.,  52  (11): [PMID:15161194] [10.1021/jf049843q]

Source

Source(1):

• Scientific Literature