forodesine   Click here for help

GtoPdb Ligand ID: 8272

Synonyms: BCX-1777 | BCX1777 | Fodosine® (proposed trade name) | immucillin H | immucillin-H
PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: Forodesine is a picomolar inhibitor of purine nucleoside phosphorylase (PNP) [1,4].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 134.26
Molecular weight 266.1
XLogP 0.72
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OCC1NC(C(C1O)O)c1c[nH]c2c1[nH]cnc2=O
Isomeric SMILES OC[C@H]1N[C@H]([C@@H]([C@@H]1O)O)c1c[nH]c2c1[nH]cnc2=O
InChI InChI=1S/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m1/s1
InChI Key IWKXDMQDITUYRK-KUBHLMPHSA-N
References
1. Kicska GA, Long L, Hörig H, Fairchild C, Tyler PC, Furneaux RH, Schramm VL, Kaufman HL. (2001)
Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes.
Proc. Natl. Acad. Sci. U.S.A., 98 (8): 4593-8. [PMID:11287638]
2. Kicska GA, Tyler PC, Evans GB, Furneaux RH, Kim K, Schramm VL. (2002)
Transition state analogue inhibitors of purine nucleoside phosphorylase from Plasmodium falciparum.
J. Biol. Chem., 277 (5): 3219-25. [PMID:11707439]
3. Kicska GA, Tyler PC, Evans GB, Furneaux RH, Schramm VL, Kim K. (2002)
Purine-less death in Plasmodium falciparum induced by immucillin-H, a transition state analogue of purine nucleoside phosphorylase.
J. Biol. Chem., 277 (5): 3226-31. [PMID:11706018]
4. Miles RW, Tyler PC, Furneaux RH, Bagdassarian CK, Schramm VL. (1998)
One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase.
Biochemistry, 37 (24): 8615-21. [PMID:9628722]