1-(2-Hydroxy-2,2-bis-phosphono-ethyl)-3-phenyl-pyridinium

ID: ALA196726

PubChem CID: 11256898

Max Phase: Preclinical

Molecular Formula: C13H16NO7P2+

Molecular Weight: 360.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(C[n+]1cccc(-c2ccccc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H15NO7P2/c15-13(22(16,17)18,23(19,20)21)10-14-8-4-7-12(9-14)11-5-2-1-3-6-11/h1-9,15H,10H2,(H3-,16,17,18,19,20,21)/p+1

Standard InChI Key:  ZYEONEYSNIUGRA-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -0.4637   -0.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -1.5185    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -2.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -0.2810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -0.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653   -0.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -2.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798   -0.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -1.5185    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798    0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653    0.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -2.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508    0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1863   -1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653    1.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508    2.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508    3.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653    3.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798    3.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798    2.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  2  9  1  0
  2 11  1  0
  4  3  1  0
  5  3  1  0
  7  3  2  0
  8  6  2  0
 16  6  1  0
  8 10  1  0
 10 12  2  0
 13 11  1  0
 15 11  1  0
 17 11  2  0
 12 14  1  0
 14 16  2  0
 14 18  1  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
M  CHG  1   6   1
M  END

Alternative Forms

1. Parent:

   

   ALA196726

   1-(2-Hydroxy-2,2-Diphosphonoethyl)-3-Phenylpyridinium

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: 360.22

Molecular Weight (Monoisotopic): 360.0397

AlogP: 0.64

#Rotatable Bonds: 5

Polar Surface Area: 139.17

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.59

CX Basic pKa: ┄

CX LogP: -4.16

CX LogD: -7.96

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: 0.20

References

1. Kotsikorou E, Song Y, Chan JM, Faelens S, Tovian Z, Broderick E, Bakalara N, Docampo R, Oldfield E..  (2005)  Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase.,  48  (19): [PMID:16162013] [10.1021/jm058220g]

2. Hudock MP, Sanz-Rodríguez CE, Song Y, Chan JM, Zhang Y, Odeh S, Kosztowski T, Leon-Rossell A, Concepción JL, Yardley V, Croft SL, Urbina JA, Oldfield E..  (2006)  Inhibition of Trypanosoma cruzi hexokinase by bisphosphonates.,  49  (1): [PMID:16392806] [10.1021/jm0582625]

Source

Source(1):

• Scientific Literature