SPRi3   Click here for help

GtoPdb Ligand ID: 10130

Synonyms: example 23 [WO2011047156] | SPR inhibitor 3
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SPRi3 is a potent small-molecule inhibitor of sepiapterin reductase [2-3], which is the terminal enzyme in the synthetic pathway for the metabolite and enzyme co-factor BH4 (also known as sapropterin). Structurally SPRi3 is a N-acetylserotonin analogue. It is one of the chemical structures (example 23) claimed in patent WO2011047156A1 [1].
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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.

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View interactive charts of activity data across species

SPRi3 is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 74.35
Molecular weight 262.13
XLogP 1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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.

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Canonical SMILES COCC(=O)NCCc1c(C)[nH]c2c1cc(O)cc2
Isomeric SMILES COCC(=O)NCCc1c(C)[nH]c2c1cc(O)cc2
InChI InChI=1S/C14H18N2O3/c1-9-11(5-6-15-14(18)8-19-2)12-7-10(17)3-4-13(12)16-9/h3-4,7,16-17H,5-6,8H2,1-2H3,(H,15,18)
InChI Key YBXBWBBVLXZQBJ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[2-(5-hydroxy-2-methyl-1H-indol-3-yl)ethyl]-2-methoxyacetamide
Synonyms Click here for help
example 23 [WO2011047156] | SPR inhibitor 3
Database Links Click here for help
BindingDB Ligand 187258
ChEMBL Ligand CHEMBL3948731
GtoPdb PubChem SID 381118840
PubChem CID 52911386
RCSB PDB Ligand 43O
Search Google for chemical match using the InChIKey YBXBWBBVLXZQBJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YBXBWBBVLXZQBJ
UniChem Compound Search for chemical match using the InChIKey YBXBWBBVLXZQBJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YBXBWBBVLXZQBJ-UHFFFAOYSA-N

Product suppliers

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Tocris
SPRi 3 (links to external site)
Cat. No. 6597