[3-(6-hydroxypyridin-3-yl)phenylamino]methylenebiphosphonic acid

ID: ALA200720

PubChem CID: 11689044

Max Phase: Preclinical

Molecular Formula: C12H14N2O7P2

Molecular Weight: 360.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Nc1cccc(-c2ccc(O)nc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C12H14N2O7P2/c15-11-5-4-9(7-13-11)8-2-1-3-10(6-8)14-12(22(16,17)18)23(19,20)21/h1-7,12,14H,(H,13,15)(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  QZXJYXJXLXFTEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   12.4111  -14.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4099  -15.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1247  -15.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8412  -15.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8383  -14.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1229  -13.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5512  -13.9478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2672  -14.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9802  -13.9424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.2704  -15.1826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.2625  -16.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0953  -15.1850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4454  -15.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6917  -13.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3965  -14.6547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5639  -13.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6986  -13.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6997  -13.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9860  -12.7161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2707  -13.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2735  -13.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9878  -14.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5555  -12.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 12  1  0
  6  1  2  0
 10 13  1  0
  1  2  1  0
  9 14  2  0
  5  7  1  0
  9 15  1  0
  3  4  1  0
  9 16  1  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  2  0
 19 20  1  0
  8 10  1  0
 20 21  2  0
  2  3  2  0
 21 22  1  0
 22 17  2  0
  1 17  1  0
 10 11  2  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200720

   [[3-(6-oxo-1H-pyridin-3-yl)anilino]-phosphonomethyl]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: 360.20

Molecular Weight (Monoisotopic): 360.0276

AlogP: 1.51

#Rotatable Bonds: 5

Polar Surface Area: 160.21

Molecular Species: ACID

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.91

CX Basic pKa: 2.14

CX LogP: -0.44

CX LogD: -3.99

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: -0.72

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