[4-fluoro-3-phenylphenylamino]methylenebiphosphonic acid

ID: ALA202878

PubChem CID: 11631880

Max Phase: Preclinical

Molecular Formula: C13H14FNO6P2

Molecular Weight: 361.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1ccc(F)c(-c2ccccc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H14FNO6P2/c14-12-7-6-10(8-11(12)9-4-2-1-3-5-9)15-13(22(16,17)18)23(19,20)21/h1-8,13,15H,(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  GYJMOIAZSFBVFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    9.4777  -24.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4766  -25.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1914  -25.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9078  -25.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9050  -24.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1896  -24.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6179  -24.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3339  -24.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468  -24.1216    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3370  -25.3618    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3292  -26.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1620  -25.3642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5120  -25.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7583  -23.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4631  -24.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6306  -23.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7653  -24.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7664  -23.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0527  -22.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3373  -23.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3402  -24.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545  -24.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618  -25.7851    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
 10 13  1  0
  1  2  2  0
  9 14  2  0
  5  7  1  0
  9 15  1  0
  3  4  2  0
  9 16  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 17  1  0
  1 17  1  0
 10 11  2  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA202878

   [4-Fluoro-3-phenylphenylamino]methylenebiphosphonic 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: 361.20

Molecular Weight (Monoisotopic): 361.0280

AlogP: 2.54

#Rotatable Bonds: 5

Polar Surface Area: 127.09

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.95

CX Basic pKa: ┄

CX LogP: 1.87

CX LogD: -2.95

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: -0.73

References

1. Hudock MP, Sanz-Rodríguez CE, Song Y, Chan JM, Zhang Y, Odeh S, Kosztowski T, Leon-Rossell A, Concepción JL, Yardley V, Croft SL, Urbina JA, Oldfield E..  (2006)  Inhibition of Trypanosoma cruzi hexokinase by bisphosphonates.,  49  (1): [PMID:16392806] [10.1021/jm0582625]

Source

Source(1):

• Scientific Literature