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

ID: ALA1093785

PubChem CID: 46885775

Max Phase: Preclinical

Molecular Formula: C9H18N4O9P2

Molecular Weight: 388.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCCC(O)(P(=O)(O)O)P(=O)(O)O)Cc1nonc1C(N)=O

Standard InChI:  InChI=1S/C9H18N4O9P2/c1-13(5-6-7(8(10)14)12-22-11-6)4-2-3-9(15,23(16,17)18)24(19,20)21/h15H,2-5H2,1H3,(H2,10,14)(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  LYOVRYZOAILBHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.5552  -11.9649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723  -12.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198  -11.9228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005  -11.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3242  -11.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310  -10.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386  -10.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844  -10.5188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -9.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454  -11.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683  -11.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294  -12.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523  -12.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134  -12.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142  -11.4353    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750  -12.1167    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833  -12.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875  -11.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708  -12.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250  -10.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083  -10.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250  -11.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206   -9.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482  -10.6365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  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
  6 23  2  0
  1  2  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093785

   [4-[(4-Carbamoyl-1,2,5-oxadiazol-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: 388.21

Molecular Weight (Monoisotopic): 388.0549

AlogP: -1.62

#Rotatable Bonds: 9

Polar Surface Area: 220.54

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.69

CX Basic pKa: 6.32

CX LogP: -5.02

CX LogD: -7.99

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.26

Np Likeness Score: -0.79

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