1-hydroxy-2-[3-(2,4-difluoro-5-methylphenyl)phenyl]ethylidene-1,1-biphosphonic acid

ID: ALA200107

PubChem CID: 11640119

Max Phase: Preclinical

Molecular Formula: C15H16F2O7P2

Molecular Weight: 408.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cccc(CC(O)(P(=O)(O)O)P(=O)(O)O)c2)c(F)cc1F

Standard InChI:  InChI=1S/C15H16F2O7P2/c1-9-5-12(14(17)7-13(9)16)11-4-2-3-10(6-11)8-15(18,25(19,20)21)26(22,23)24/h2-7,18H,8H2,1H3,(H2,19,20,21)(H2,22,23,24)

Standard InChI Key:  AIIFWEAZXJDTSZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    0.8845  -13.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005  -13.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123  -14.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108  -13.2117    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935  -14.6448    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165  -12.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7276  -13.6199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947  -12.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749  -15.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078  -15.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4797  -14.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833  -13.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984  -13.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2988  -13.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178  -14.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9300  -14.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1317  -14.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790  -12.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632  -11.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425  -11.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0414  -11.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2577  -12.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768  -12.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653  -11.7563    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6224  -11.0034    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550  -12.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  2  0
  4  8  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  5  9  2  0
 14 18  1  0
  2  5  1  0
 18 19  2  0
  5 10  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
  5 11  1  0
 21 22  1  0
  4  6  2  0
 22 23  2  0
 23 18  1  0
  1 12  1  0
 19 24  1  0
  1  2  1  0
 21 25  1  0
 12 13  2  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200107

   1-Hydroxy-2-[3-(2,4-difluoro-5-methylphenyl)phenyl]ethylidene-1,1-biphosphonic 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: 408.23

Molecular Weight (Monoisotopic): 408.0339

AlogP: 2.48

#Rotatable Bonds: 5

Polar Surface Area: 135.29

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: -3.04

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: -0.29

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