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

ID: ALA425925

PubChem CID: 11601799

Max Phase: Preclinical

Molecular Formula: C8H13NO7P2

Molecular Weight: 297.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cccc(CC(O)(P(=O)(O)O)P(=O)(O)O)c1

Standard InChI:  InChI=1S/C8H13NO7P2/c9-7-3-1-2-6(4-7)5-8(10,17(11,12)13)18(14,15)16/h1-4,10H,5,9H2,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  PFCOEWWKLLBGMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.9125   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -3.1542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.6125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -3.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -3.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -3.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375   -1.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -3.1542    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 12  2  0
 14 13  1  0
 15 14  1  0
 16 17  2  0
 17 12  1  0
 18 16  1  0
 14 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA425925

   [2-(3-Amino-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: 297.14

Molecular Weight (Monoisotopic): 297.0167

AlogP: -0.19

#Rotatable Bonds: 4

Polar Surface Area: 161.31

Molecular Species: ACID

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.66

CX Basic pKa: 4.23

CX LogP: -2.28

CX LogD: -6.26

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.33

Np Likeness Score: 0.07

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