puromycin   Click here for help

GtoPdb Ligand ID: 13311

Synonyms: achromycin
PDB Ligand
Compound class: Natural product
Comment: Puromycin is an aminoacyl nucleoside antimicrobial compound, originally isolated from Streptomyces alboniger [4]. It is a potent inhibitor of protein translation in both eukaryotic and prokaryotic organisms [5] and has not been of clinical utility due to its non-selective systemic toxicity. Instead it is used extensively in the laboratory to study mechanisms of protein synthesis and also as a selective agent in mammalian cell culture systems (reviewed in [2]).
Please note that puromycin was formerly known as achromycin, which was also a trade name used for tetracycline.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
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 12
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 157.6
Molecular weight 471.51
XLogP -1.28
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 CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@@H](CO)O3)NC(=O)[C@H](CC4=CC=C(C=C4)OC)N)O
Isomeric SMILES CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](CC4=CC=C(C=C4)OC)N)O
InChI InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1
InChI Key RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(2S)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylaminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
International Nonproprietary Names Click here for help
INN number INN
1962 puromycin
Synonyms Click here for help
achromycin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Puromycin
Other databases
BindingDB Ligand 50277158
CAS Registry No. 53-79-2 (source: Scifinder)
ChEBI CHEBI:17939
ChEMBL Ligand CHEMBL469912
DrugBank Ligand DB08437
GtoPdb PubChem SID 496703281
PubChem CID 439530
RCSB PDB Ligand PUY
Search Google for chemical match using the InChIKey RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Search Google for chemicals with the same backbone RXWNCPJZOCPEPQ
Search PubMed clinical trials puromycin
Search PubMed titles puromycin
Search PubMed titles/abstracts puromycin
UniChem Compound Search for chemical match using the InChIKey RXWNCPJZOCPEPQ-NVWDDTSBSA-N
UniChem Connectivity Search for chemical match using the InChIKey RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Wikipedia Puromycin