[4-(N-Methyl-N-[(3-carbamoylfuroxan-4-yl)methyl]-1-hydroxybutylidene]bis(phosphonic) acid

ID: ALA1088773

PubChem CID: 46885776

Max Phase: Preclinical

Molecular Formula: C9H18N4O10P2

Molecular Weight: 404.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCCC(O)(P(=O)(O)O)P(=O)(O)O)Cc1no[n+]([O-])c1C(N)=O

Standard InChI:  InChI=1S/C9H18N4O10P2/c1-12(5-6-7(8(10)14)13(16)23-11-6)4-2-3-9(15,24(17,18)19)25(20,21)22/h15H,2-5H2,1H3,(H2,10,14)(H2,17,18,19)(H2,20,21,22)

Standard InChI Key:  LNBBYSVYUHGJNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   10.5031  -12.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1860  -12.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8386  -12.0770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5578  -11.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7341  -11.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2273  -10.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0197  -10.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8427  -10.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3046   -9.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2037  -11.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0267  -11.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3877  -12.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2107  -12.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5717  -13.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6726  -11.5895    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.0333  -12.2708    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.4417  -12.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7458  -11.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8292  -12.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0833  -11.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6667  -10.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3833  -11.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9125  -12.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5377   -9.9129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4102  -10.7906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 12 13  1  0
 13 14  1  0
  4  7  1  0
 13 15  1  0
  2  3  1  0
 13 16  1  0
  7  8  1  0
 16 17  2  0
  3  4  2  0
 16 18  1  0
  8  9  1  0
 16 19  1  0
  4  5  1  0
 15 20  2  0
  8 10  1  0
 15 21  1  0
  5  1  2  0
 15 22  1  0
 10 11  1  0
  1 23  1  0
  1  2  1  0
  6 24  2  0
 11 12  1  0
  6 25  1  0
M  CHG  2   1   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1088773

   [4-[(4-Carbamoyl-5-oxido-1,2,5-oxadiazol-5-ium-3-yl)methyl-methylamino]-1-hydroxy-1-phosphonobutyl]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: 404.21

Molecular Weight (Monoisotopic): 404.0498

AlogP: -2.38

#Rotatable Bonds: 9

Polar Surface Area: 234.59

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.69

CX Basic pKa: 5.77

CX LogP: -7.39

CX LogD: -10.27

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.19

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