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
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydropyrrolo[2,3-e]pyrimidin-4-one
International Nonproprietary Names Click here for help
INN number INN
8558 forodesine
Synonyms Click here for help
BCX-1777 | BCX1777 | Fodosine® (proposed trade name) | immucillin H | immucillin-H
Database Links Click here for help
CAS Registry No. 209799-67-7
ChEBI CHEBI:43362
ChEMBL Ligand CHEMBL218291
DrugCentral Ligand 5229
GtoPdb PubChem SID 252166484
PubChem CID 135409409
RCSB PDB Ligand IMH
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SynPHARM 81910 (in complex with purine nucleoside phosphorylase)
Wikipedia Forodesine