gemcitabine   Click here for help

GtoPdb Ligand ID: 4793

Synonyms: gemcitabine hydrochloride | Gemzar®
Approved drug PDB Ligand
gemcitabine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Gemcitabine is a nucleoside analogue chemotherapeutic. Chemically, the hydrogen atoms on the 2' carbon of deoxycytidine are replaced by fluorine atoms.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 110.6
Molecular weight 263.07
XLogP 0.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)(F)F)n1ccc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H](C([C@@H]1O)(F)F)n1ccc(nc1=O)N
InChI InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
InChI Key SDUQYLNIPVEERB-QPPQHZFASA-N