SCH772984   Click here for help

GtoPdb Ligand ID: 8056

Synonyms: SCH-772984
PDB Ligand
Compound class: Synthetic organic
Comment: SCH772984 is an experimental inhibitor of the mitogen-activated protein kinases ERK1 and ERK2 [2]. The in vitro mechanism of action of SCH772984 is notable, in that it inhibits both the catalytic activity of ERK1/2 and also inhibits phosphorylation of ERK1/2. This is in contrast to other ERK inhibitors that target the ATP-binding site and thus inhibit only the catalytic activity of the kinases. The dual action of compounds like SCH772984 is predicted to block the nuclear localization of pERK and more completely suppress MAPK pathway signaling [2]. This type of inhibitor may provide improved clinical efficacy, particularly in relation to the emergence of acquired resistance that occurs in BRAF and MEK inhibitor-treated cancers. Unfortunately, SCH772984 is not active in vivo (oral or intraperitoneal administration results in poor exposure levels) [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
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 10
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 123.24
Molecular weight 587.28
XLogP 2.69
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 O=C(N1CCN(CC1)c1ccc(cc1)c1ncccn1)CN1CCC(C1)C(=O)Nc1ccc2c(c1)c(n[nH]2)c1ccncc1
Isomeric SMILES O=C(N1CCN(CC1)c1ccc(cc1)c1ncccn1)CN1CC[C@H](C1)C(=O)Nc1ccc2c(c1)c(n[nH]2)c1ccncc1
InChI InChI=1S/C33H33N9O2/c43-30(42-18-16-41(17-19-42)27-5-2-24(3-6-27)32-35-11-1-12-36-32)22-40-15-10-25(21-40)33(44)37-26-4-7-29-28(20-26)31(39-38-29)23-8-13-34-14-9-23/h1-9,11-14,20,25H,10,15-19,21-22H2,(H,37,44)(H,38,39)/t25-/m1/s1
InChI Key HDAJDNHIBCDLQF-RUZDIDTESA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3R)-1-[2-oxo-2-[4-(4-pyrimidin-2-ylphenyl)piperazin-1-yl]ethyl]-N-(3-pyridin-4-yl-1H-indazol-5-yl)pyrrolidine-3-carboxamide
Synonyms Click here for help
SCH-772984
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9657543
Reactome Reaction Reactome logo R-HSA-9657603
Other databases
CAS Registry No. 942183-80-4
GtoPdb PubChem SID 249565736
PubChem CID 24866313
RCSB PDB Ligand 38Z, F3Z
Search Google for chemical match using the InChIKey HDAJDNHIBCDLQF-RUZDIDTESA-N
Search Google for chemicals with the same backbone HDAJDNHIBCDLQF
SynPHARM 81089 (in complex with mitogen-activated protein kinase 1)
81090 (in complex with mitogen-activated protein kinase 1)
UniChem Compound Search for chemical match using the InChIKey HDAJDNHIBCDLQF-RUZDIDTESA-N
UniChem Connectivity Search for chemical match using the InChIKey HDAJDNHIBCDLQF-RUZDIDTESA-N