olodanrigan   Click here for help

GtoPdb Ligand ID: 8374

Synonyms: [S]-enantiomer of EMA400 [9] | [S]-enantiomer of PD-126,055 | EMA-401 | EMA401
PDB Ligand
Compound class: Synthetic organic
Comment: Olodanrigan (EMA401) is reported as a selective antagonist of the angiotensin type II receptor (AT2R) [6,9]. The compound is being assessed as a novel therapy for neuropathic pain [3].
Note that PubChem CID 23683656 refers to the potassium salt and that the sodium salt was used in [9].
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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

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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 4
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 76.07
Molecular weight 507.2
XLogP 5.36
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccc2c(c1OCc1ccccc1)CC(N(C2)C(=O)C(c1ccccc1)c1ccccc1)C(=O)O
Isomeric SMILES COc1ccc2c(c1OCc1ccccc1)C[C@H](N(C2)C(=O)C(c1ccccc1)c1ccccc1)C(=O)O
InChI InChI=1S/C32H29NO5/c1-37-28-18-17-25-20-33(31(34)29(23-13-7-3-8-14-23)24-15-9-4-10-16-24)27(32(35)36)19-26(25)30(28)38-21-22-11-5-2-6-12-22/h2-18,27,29H,19-21H2,1H3,(H,35,36)/t27-/m0/s1
InChI Key GHBCIXGRCZIPNQ-MHZLTWQESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S)-2-(2,2-diphenylacetyl)-6-methoxy-5-phenylmethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
10476 olodanrigan
Synonyms Click here for help
[S]-enantiomer of EMA400 [9] | [S]-enantiomer of PD-126,055 | EMA-401 | EMA401
Database Links Click here for help
Specialist databases
GPCRdb Ligand olodanrigan
Other databases
BindingDB Ligand 50282401
CAS Registry No. 1316755-16-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL34124
GtoPdb PubChem SID 252166586
PubChem CID 9937291
RCSB PDB Ligand VFD
Search Google for chemical match using the InChIKey GHBCIXGRCZIPNQ-MHZLTWQESA-N
Search Google for chemicals with the same backbone GHBCIXGRCZIPNQ
Search PubMed clinical trials olodanrigan
Search PubMed titles olodanrigan
Search PubMed titles/abstracts olodanrigan
UniChem Compound Search for chemical match using the InChIKey GHBCIXGRCZIPNQ-MHZLTWQESA-N
UniChem Connectivity Search for chemical match using the InChIKey GHBCIXGRCZIPNQ-MHZLTWQESA-N

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MedChemExpress
Olodanrigan (links to external site)
Cat. No. HY-13106