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
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
Search Google for chemical match using the InChIKey NHTKGYOMICWFQZ-BSMFTPRPSA-N
Search Google for chemicals with the same backbone NHTKGYOMICWFQZ
UniChem Compound Search for chemical match using the InChIKey NHTKGYOMICWFQZ-BSMFTPRPSA-N
UniChem Connectivity Search for chemical match using the InChIKey NHTKGYOMICWFQZ-BSMFTPRPSA-N