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

ID: ALA1091521

PubChem CID: 46885728

Max Phase: Preclinical

Molecular Formula: C13H18N2O10P2

Molecular Weight: 424.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(CCCCOc1no[n+]([O-])c1-c1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H18N2O10P2/c16-13(26(18,19)20,27(21,22)23)8-4-5-9-24-12-11(15(17)25-14-12)10-6-2-1-3-7-10/h1-3,6-7,16H,4-5,8-9H2,(H2,18,19,20)(H2,21,22,23)

Standard InChI Key:  IOUTWBBKMSRKHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.1927  -22.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5098  -23.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573  -22.8145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380  -22.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9617  -22.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684  -21.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535  -20.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6595  -20.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776  -20.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872  -20.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794  -21.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173  -21.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077  -21.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5283  -20.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533  -20.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740  -19.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989  -19.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0196  -19.2256    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032  -20.6544    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825  -21.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504  -21.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077  -20.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633  -18.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7519  -19.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029  -18.7663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690  -23.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208  -19.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  1 26  1  0
  5  6  1  0
 17 27  1  0
M  CHG  2   1   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1091521

   [1-Hydroxy-5-[(5-oxido-4-phenyl-1,2,5-oxadiazol-5-ium-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: 424.24

Molecular Weight (Monoisotopic): 424.0437

AlogP: 0.53

#Rotatable Bonds: 9

Polar Surface Area: 197.49

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: -1.61

CX LogD: -6.46

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.21

Np Likeness Score: -0.07

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