[2-(3-Dimethylaminomethyl-phenyl)-1-hydroxy-1-phosphono-ethyl]-phosphonic acid

ID: ALA199254

PubChem CID: 5277502

Max Phase: Preclinical

Molecular Formula: C11H19NO7P2

Molecular Weight: 339.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1cccc(CC(O)(P(=O)(O)O)P(=O)(O)O)c1

Standard InChI:  InChI=1S/C11H19NO7P2/c1-12(2)8-10-5-3-4-9(6-10)7-11(13,20(14,15)16)21(17,18)19/h3-6,13H,7-8H2,1-2H3,(H2,14,15,16)(H2,17,18,19)

Standard InChI Key:  BXKVPYZFERQXNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    9.2000   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2000   -4.2125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.6042   -2.6667    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3750   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917   -2.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917   -5.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -1.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -2.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -1.7417    0.0000 C   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  2  2  0
  6  3  2  0
  7  1  1  0
  8  2  1  0
  9  2  1  0
 10  3  1  0
 11  3  1  0
 12  4  1  0
 13 14  1  0
 14 12  2  0
 15 13  1  0
 16 15  1  0
 17 18  2  0
 18 12  1  0
 19 17  1  0
 20 16  1  0
 21 16  1  0
 13 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA199254

   [2-[3-(Dimethylaminomethyl)phenyl]-1-hydroxy-1-phosphono-ethyl]phosphonic 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: 339.22

Molecular Weight (Monoisotopic): 339.0637

AlogP: 0.29

#Rotatable Bonds: 6

Polar Surface Area: 138.53

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.68

CX Basic pKa: 8.93

CX LogP: -2.44

CX LogD: -4.82

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: -0.31

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]

Source

Source(1):

• Scientific Literature