(5-(4-Phenylfurazan-3-yloxy)-1-hydroxypentylidene)-bis(phosphonic) acid

ID: ALA1091520

PubChem CID: 46885727

Max Phase: Preclinical

Molecular Formula: C13H18N2O9P2

Molecular Weight: 408.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(CCCCOc1nonc1-c1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H18N2O9P2/c16-13(25(17,18)19,26(20,21)22)8-4-5-9-23-12-11(14-24-15-12)10-6-2-1-3-7-10/h1-3,6-7,16H,4-5,8-9H2,(H2,17,18,19)(H2,20,21,22)

Standard InChI Key:  YKFHYEBQVOEUAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    8.1240  -15.5774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8068  -16.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594  -15.5353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1794  -14.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3545  -14.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9297  -14.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3338  -13.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097  -12.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839  -12.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6841  -13.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1105  -14.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6074  -14.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4322  -14.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8609  -13.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6857  -13.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1145  -12.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9392  -12.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3680  -11.9940    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3353  -13.4226    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.9065  -14.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7746  -14.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1378  -13.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3211  -11.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0960  -12.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0565  -11.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7333  -12.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 12 13  1  0
 13 14  1  0
  6  7  2  0
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  2  0
 17 18  1  0
  8  9  2  0
 17 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 19 21  1  0
  5  1  2  0
 19 22  1  0
 10 11  2  0
 18 23  1  0
 11  6  1  0
 18 24  2  0
  1  2  1  0
 18 25  1  0
  4 12  1  0
 17 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091520

   [1-Hydroxy-5-[(4-phenyl-1,2,5-oxadiazol-3-yl)oxy]-1-phosphonopentyl]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: 408.24

Molecular Weight (Monoisotopic): 408.0488

AlogP: 1.29

#Rotatable Bonds: 9

Polar Surface Area: 183.44

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: -4.51

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.30

Np Likeness Score: -0.36

References

1. Lolli ML, Rolando B, Tosco P, Chaurasia S, Di Stilo A, Lazzarato L, Gorassini E, Ferracini R, Oliaro-Bosso S, Fruttero R, Gasco A..  (2010)  Synthesis and preliminary pharmacological characterisation of a new class of nitrogen-containing bisphosphonates (N-BPs).,  18  (7): [PMID:20299227] [10.1016/j.bmc.2010.02.058]

Source

Source(1):

• Scientific Literature