5-(4-Phenylsulfonylfurazan-3-yloxy)pentylidenebis(phosphonic) acid

ID: ALA1093435

PubChem CID: 46885684

Max Phase: Preclinical

Molecular Formula: C13H18N2O10P2S

Molecular Weight: 456.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(CCCCOc1nonc1S(=O)(=O)c1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H18N2O10P2S/c16-26(17,18)11(27(19,20)21)8-4-5-9-24-12-13(15-25-14-12)28(22,23)10-6-2-1-3-7-10/h1-3,6-7,11H,4-5,8-9H2,(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  MMZZEFWKJCYZRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    8.7832   -8.0701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4657   -8.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1181   -8.0282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8382   -7.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0136   -7.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2660   -6.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0905   -6.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5190   -5.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3435   -5.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7722   -5.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5965   -5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0252   -4.4881    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.9925   -5.9162    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.5639   -6.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4316   -6.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7947   -6.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9783   -3.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7529   -4.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7134   -4.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5062   -6.6297    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9178   -6.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1379   -5.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5503   -4.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439   -4.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5284   -5.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1175   -6.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7887   -7.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2188   -6.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
  6  7  1  0
 13 15  1  0
  2  3  1  0
 13 16  1  0
  7  8  1  0
 12 17  1  0
  3  4  2  0
 12 18  2  0
  8  9  1  0
 12 19  1  0
  4  5  1  0
  5 20  1  0
  9 10  1  0
 20 21  1  0
  5  1  2  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  4  6  1  0
 25 26  2  0
 26 21  1  0
 11 13  1  0
 20 27  2  0
 20 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093435

   [5-[[4-(Benzenesulfonyl)-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: 456.31

Molecular Weight (Monoisotopic): 456.0157

AlogP: 1.13

#Rotatable Bonds: 10

Polar Surface Area: 197.35

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.21

CX Basic pKa: ┄

CX LogP: 0.00

CX LogD: -4.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: -0.86

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