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

ID: ALA1091027

PubChem CID: 46885729

Max Phase: Preclinical

Molecular Formula: C13H18N2O12P2S

Molecular Weight: 488.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(CCCCOc1no[n+]([O-])c1S(=O)(=O)c1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H18N2O12P2S/c16-13(28(18,19)20,29(21,22)23)8-4-5-9-26-11-12(15(17)27-14-11)30(24,25)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:  WDZVZCQRPQEIFO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    2.2865  -27.9565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693  -28.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219  -27.9145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3412  -27.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174  -27.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619  -26.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868  -26.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075  -25.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325  -25.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2531  -25.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0781  -25.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4988  -24.3256    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.4823  -25.7544    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0617  -26.4641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9295  -26.4399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2868  -25.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4425  -23.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2311  -24.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1821  -23.8663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102  -28.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107  -26.5148    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211  -25.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393  -25.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4498  -24.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428  -24.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218  -24.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8151  -25.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917  -25.7958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083  -26.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8708  -25.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  1 20  1  0
  9 10  1  0
  5 21  1  0
  5  1  2  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
  4  6  1  0
 25 26  1  0
 11 13  1  0
 26 27  2  0
 27 22  1  0
 21 28  2  0
 13 14  2  0
 21 29  2  0
  6  7  1  0
 11 30  1  0
M  CHG  2   1   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1091027

   (5-(3-Phenylsulfonylfuroxan-4-yloxy)-1-hydroxypentylidene)bis(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: 488.30

Molecular Weight (Monoisotopic): 488.0056

AlogP: -0.31

#Rotatable Bonds: 10

Polar Surface Area: 231.63

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: -2.29

CX LogD: -7.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.16

Np Likeness Score: -0.45

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