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

ID: ALA414849

Cas Number: 427899-21-6

PubChem CID: 9994754

Product Number: N612204, Order Now?

Max Phase: Preclinical

Molecular Formula: C8H13NO7P2

Molecular Weight: 297.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1CC(O)(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C8H13NO7P2/c9-7-4-2-1-3-6(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:  VJXYJONFUZXZJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    9.1373    0.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1359   -0.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8489   -1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5682   -0.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5651    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8469    0.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2774    0.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9940    0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4056    0.8590    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.8099    1.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1224    0.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6893    1.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5725   -0.5637    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.6999   -0.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1555   -1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8623   -0.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2826   -0.9836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8431    1.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  9 10  1  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
  9 12  2  0
  6  1  1  0
  8 13  1  0
  1  2  2  0
  8 14  1  0
  5  7  1  0
 13 15  1  0
  3  4  2  0
 13 16  2  0
  7  8  1  0
 13 17  1  0
  6 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA414849

   NE21650

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: 0.65

CX Basic pKa: 3.64

CX LogP: -2.28

CX LogD: -6.27

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.33

Np Likeness Score: 0.16

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. Dunford JE, Kwaasi AA, Rogers MJ, Barnett BL, Ebetino FH, Russell RG, Oppermann U, Kavanagh KL..  (2008)  Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.,  51  (7): [PMID:18327899] [10.1021/jm7015733]

3. Hounslow AM, Carran J, Brown RJ, Rejman D, Blackburn GM, Watts DJ..  (2008)  Determination of the microscopic equilibrium dissociation constants for risedronate and its analogues reveals two distinct roles for the nitrogen atom in nitrogen-containing bisphosphonate drugs.,  51  (14): [PMID:18590315] [10.1021/jm7015792]

4. Song Y, Chan JM, Tovian Z, Secrest A, Nagy E, Krysiak K, Bergan K, Parniak MA, Oldfield E..  (2008)  Bisphosphonate inhibitors of ATP-mediated HIV-1 reverse transcriptase catalyzed excision of chain-terminating 3'-azido, 3'-deoxythymidine: a QSAR investigation.,  16  (19): [PMID:18789701] [10.1016/j.bmc.2008.08.047]

Source

Source(1):

• Scientific Literature