acelarin   Click here for help

GtoPdb Ligand ID: 7389

Synonyms: NUC-1031
Compound class: Synthetic organic
Comment: Acelerin is a candidate pro-drug. The proposed route to the active monophosphate form is depicted in Scheme 4 in [2]. Acerlarin is an analogue of gemcitabine, the main therapeutic used to treat pancreatic cancer. Acelarin is termed a ProTide, and structurally is gemcitabine with an attached phosphoramidate group. The aim of this chemical modification is to achieve improved cellular delivery of the activated drug, overcoming resistance mechanisms and protecting against enzymatic breakdown to toxic byproducts [2], and hopefully achieving better disease response. The chemical structure depicted here was drawn from [2] where acelerin is compound 6f.

Acelarin is the first ProTide to reach clinical trial and is only one member of a large development pipeline covering many nucleoside anti-metabolite anti-neoplastic drugs.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 174.04
Molecular weight 580.15
XLogP 3.18
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C(C(NP(=O)(Oc1ccccc1)OCC1OC(C(C1O)(F)F)n1ccc(nc1=O)N)C)OCc1ccccc1
Isomeric SMILES O=C([C@@H](NP(=O)(Oc1ccccc1)OC[C@H]1O[C@H](C([C@H]1O)(F)F)n1ccc(nc1=O)N)C)OCc1ccccc1
InChI InChI=1S/C25H27F2N4O8P/c1-16(22(33)36-14-17-8-4-2-5-9-17)30-40(35,39-18-10-6-3-7-11-18)37-15-19-21(32)25(26,27)23(38-19)31-13-12-20(28)29-24(31)34/h2-13,16,19,21,23,32H,14-15H2,1H3,(H,30,35)(H2,28,29,34)/t16-,19+,21-,23+,40?/m0/s1
InChI Key NHTKGYOMICWFQZ-BSMFTPRPSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
benzyl (2S)-2-[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(phenoxy)phosphoryl)amino]propanoate
Synonyms Click here for help
NUC-1031
Database Links Click here for help
GtoPdb PubChem SID 178103961
PubChem CID 73755261
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