(4-chlorophenylamino)methylenediphosphonic acid

ID: ALA2440579

PubChem CID: 15629940

Max Phase: Preclinical

Molecular Formula: C7H10ClNO6P2

Molecular Weight: 301.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1ccc(Cl)cc1)P(=O)(O)O

Standard InChI:  InChI=1S/C7H10ClNO6P2/c8-5-1-3-6(4-2-5)9-7(16(10,11)12)17(13,14)15/h1-4,7,9H,(H2,10,11,12)(H2,13,14,15)

Standard InChI Key:  PPOZCMYPJMEBPT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   18.5308   -3.0988    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.9420   -3.8050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3480   -3.0957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2339   -1.8704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.6451   -2.5765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0510   -1.8673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6986   -2.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6974   -3.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4055   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1151   -3.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1123   -2.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4037   -1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8185   -1.8757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5277   -2.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8246   -3.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2308   -1.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9894   -3.5181    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
M  END

Alternative Forms

1. Parent:

   

   ALA2440579

   (4-CHLOROPHENYLAMINO)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: 301.56

Molecular Weight (Monoisotopic): 300.9672

AlogP: 1.39

#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: 0.63

CX LogD: -4.19

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.53

Np Likeness Score: -0.66

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]

Source

Source(1):

• Scientific Literature