fludarabine   Click here for help

GtoPdb Ligand ID: 4802

Synonyms: 2-F-Ara-A | CCRIS 3382 | F-Ara-A | Fludara®
Approved drug
fludarabine is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Fludarabine is a chemotherapy drug used to treat blood cancers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 139.54
Molecular weight 285.09
XLogP -1.17
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1nc(F)nc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1nc(F)nc2N
InChI InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
InChI Key HBUBKKRHXORPQB-FJFJXFQQSA-N
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Sodium/nucleoside cotransporter 2 2
Equilibrative nucleoside transporter 3 1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ribonucleotide reductase catalytic subunit M1 Primary target of this compound Hs Inhibitor Inhibition 6.0 pIC50 - 3
pIC50 6.0 (IC50 1x10-6 M) [3]
Description: Inhibition of ADP reduction by ribonucleotide reductase from HeLa cells
ribonucleotide reductase regulatory subunit M2 Primary target of this compound Hs Inhibitor Inhibition 6.0 pIC50 - 3
pIC50 6.0 (IC50 1x10-6 M) [3]
Description: Inhibition of ADP reduction by ribonucleotide reductase from HeLa cells