1-hydroxy-2-[3-(6-hydroxypyridin-3-yl)phenyl]ethylidene-1,1-biphosphonic acid

ID: ALA199654

PubChem CID: 11581589

Max Phase: Preclinical

Molecular Formula: C13H15NO8P2

Molecular Weight: 375.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(Cc1cccc(-c2ccc(O)nc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C13H15NO8P2/c15-12-5-4-11(8-14-12)10-3-1-2-9(6-10)7-13(16,23(17,18)19)24(20,21)22/h1-6,8,16H,7H2,(H,14,15)(H2,17,18,19)(H2,20,21,22)

Standard InChI Key:  VNEJJZFEJZQSIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    6.6504  -14.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3654  -15.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0764  -15.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7753  -14.5385    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.9590  -15.9699    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1804  -13.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4911  -14.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0601  -14.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410  -16.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6724  -16.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461  -15.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8502  -15.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2693  -14.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699  -14.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512  -15.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382  -16.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6355  -15.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870  -14.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060  -13.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5274  -12.7093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296  -12.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212  -13.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937  -14.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467  -12.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12 13  2  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
  2  5  1  0
 18 19  1  0
  5 10  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
  5 11  1  0
 21 22  2  0
  4  6  2  0
 22 23  1  0
 23 18  2  0
 14 18  1  0
  1 12  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA199654

   [1-hydroxy-2-[3-(6-oxo-1H-pyridin-3-yl)phenyl]-1-phosphonoethyl]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: 375.21

Molecular Weight (Monoisotopic): 375.0273

AlogP: 1.00

#Rotatable Bonds: 5

Polar Surface Area: 168.41

Molecular Species: ACID

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.66

CX Basic pKa: 2.07

CX LogP: -1.27

CX LogD: -4.72

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.42

Np Likeness Score: -0.17

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