ID: ALA1099309

Max Phase: Preclinical

Molecular Formula: C10H11N2O6P

Molecular Weight: 286.18

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)C(O)(Cc1cnc2ccccn12)P(=O)(O)O

Standard InChI:  InChI=1S/C10H11N2O6P/c13-9(14)10(15,19(16,17)18)5-7-6-11-8-3-1-2-4-12(7)8/h1-4,6,15H,5H2,(H,13,14)(H2,16,17,18)

Standard InChI Key:  XZINREBMYQRVSH-UHFFFAOYSA-N

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

Properties

Molecular Weight: 286.18

Molecular Weight (Monoisotopic): 286.0355

AlogP: -0.17

#Rotatable Bonds: 4

Polar Surface Area: 132.36

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.05

CX Basic pKa: 6.09

CX LogP: -2.55

CX LogD: -5.74

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.57

Np Likeness Score: -0.73

References

1. McKenna CE, Kashemirov BA, Błazewska KM, Mallard-Favier I, Stewart CA, Rojas J, Lundy MW, Ebetino FH, Baron RA, Dunford JE, Kirsten ML, Seabra MC, Bala JL, Marma MS, Rogers MJ, Coxon FP..  (2010)  Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid.,  53  (9): [PMID:20394422] [10.1021/jm900232u]

2. McKenna CE, Kashemirov BA, Błazewska KM, Mallard-Favier I, Stewart CA, Rojas J, Lundy MW, Ebetino FH, Baron RA, Dunford JE, Kirsten ML, Seabra MC, Bala JL, Marma MS, Rogers MJ, Coxon FP..  (2010)  Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid.,  53  (9): [PMID:20394422] [10.1021/jm900232u]

3. McKenna CE, Kashemirov BA, Błazewska KM, Mallard-Favier I, Stewart CA, Rojas J, Lundy MW, Ebetino FH, Baron RA, Dunford JE, Kirsten ML, Seabra MC, Bala JL, Marma MS, Rogers MJ, Coxon FP..  (2010)  Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid.,  53  (9): [PMID:20394422] [10.1021/jm900232u]

4. Błażewska KM, Ni F, Haiges R, Kashemirov BA, Coxon FP, Stewart CA, Baron R, Rogers MJ, Seabra MC, Ebetino FH, McKenna CE..  (2011)  Synthesis, stereochemistry and SAR of a series of minodronate analogues as RGGT inhibitors.,  46  (10): [PMID:21889236] [10.1016/j.ejmech.2011.04.063]

5. Ochocki JD, Distefano MD..  (2013)  Prenyltransferase Inhibitors: Treating Human Ailments from Cancer to Parasitic Infections.,  4  (3): [PMID:25530833] [10.1039/c2md20299a]

6. Kaźmierczak A, Kusy D, Niinivehmas SP, Gmach J, Joachimiak Ł, Pentikäinen OT, Gendaszewska-Darmach E, Błażewska KM..  (2017)  Identification of the Privileged Position in the Imidazo[1,2-a]pyridine Ring of Phosphonocarboxylates for Development of Rab Geranylgeranyl Transferase (RGGT) Inhibitors.,  60  (21): [PMID:28953373] [10.1021/acs.jmedchem.7b00811]

Source

Source(1):

• Scientific Literature