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

ID: ALA1093434

PubChem CID: 46885683

Max Phase: Preclinical

Molecular Formula: C13H18N2O9P2

Molecular Weight: 408.24

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  IWJQOGFLQREZFX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -2.9010   -8.2940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -8.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -8.2520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -7.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701   -7.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1767   -6.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8619   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3678   -5.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859   -5.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -6.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9877   -6.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256   -6.7637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -6.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1800   -6.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450   -6.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -5.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8906   -5.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3113   -4.6631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948   -6.0919    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742   -6.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -6.7774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993   -6.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550   -3.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436   -5.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -4.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773   -8.5734    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
  1 26  1  0
M  CHG  2   1   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1093434

   5-(3-Phenylfuroxan-4-yloxy)pentylidenebis(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: 1.21

#Rotatable Bonds: 9

Polar Surface Area: 177.26

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.21

CX Basic pKa: ┄

CX LogP: -1.58

CX LogD: -6.24

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.27

Np Likeness Score: -0.20

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