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

ID: ALA1091856

PubChem CID: 46866079

Product Number: B608917, Order Now?

Max Phase: Preclinical

Molecular Formula: C13H18N2O11P2S

Molecular Weight: 472.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H18N2O11P2S/c16-13(27(17,18)19,28(20,21)22)8-4-5-9-25-11-12(15-26-14-11)29(23,24)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:  PSWFNEHHRVMWEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    9.9594  -21.7644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6421  -22.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2945  -21.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0146  -20.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1899  -20.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4425  -20.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2671  -20.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6957  -19.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5204  -19.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9491  -18.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7736  -18.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2023  -18.1819    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.1696  -19.6101    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.7409  -20.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6088  -20.3005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9719  -19.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1554  -17.3568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9301  -18.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8907  -17.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6824  -20.3237    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0939  -19.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3140  -18.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7264  -18.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9198  -18.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7043  -19.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2935  -19.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9648  -20.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3951  -19.9086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5675  -19.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 13 14  2  0
 11 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091856

   (5-{[4-(benzenesulfonyl)-1,2,5-oxadiazol-3-yl]oxy}-1-hydroxy-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: 472.31

Molecular Weight (Monoisotopic): 472.0107

AlogP: 0.45

#Rotatable Bonds: 10

Polar Surface Area: 217.58

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: -0.14

CX LogD: -5.07

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: -0.72

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